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N,N'-DIACETYLETHYLENEDIAMINE, also known as diacetyl ethylenediamine, is a synthetic compound with the chemical formula C6H10N2O2. It is derived from ethylenediamine and acetic anhydride and is characterized by its crystalline solid form and solubility in water. With a molecular weight of 142.16 g/mol, this compound is primarily used for forming chemical bonds between different molecules, making it a vital ingredient in various industries.

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  • 871-78-3 Structure
  • Basic information

    1. Product Name: N,N'-DIACETYLETHYLENEDIAMINE
    2. Synonyms: N,N'-ETHYLENEBISACETAMIDE;N,N'-DIACETYLETHYLENEDIAMINE;N1-[2-(ACETYLAMINO)ETHYL]ACETAMIDE;TIMTEC-BB SBB007829;1,2-ETHYLENEBISACETAMIDE;ETHYLENE BISACETAMIDE;N,N'-ethylenedi(diacetamide);N,N'-Diacetylethylenediamine,98%
    3. CAS NO:871-78-3
    4. Molecular Formula: C6H12N2O2
    5. Molecular Weight: 144.17
    6. EINECS: 212-811-9
    7. Product Categories: N/A
    8. Mol File: 871-78-3.mol
    9. Article Data: 35
  • Chemical Properties

    1. Melting Point: 170-172°C
    2. Boiling Point: 438.7 °C at 760 mmHg
    3. Flash Point: 214.8 °C
    4. Appearance: /
    5. Density: 1.033 g/cm3
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. PKA: 15.67±0.46(Predicted)
    10. Water Solubility: almost transparency
    11. BRN: 1762229
    12. CAS DataBase Reference: N,N'-DIACETYLETHYLENEDIAMINE(CAS DataBase Reference)
    13. NIST Chemistry Reference: N,N'-DIACETYLETHYLENEDIAMINE(871-78-3)
    14. EPA Substance Registry System: N,N'-DIACETYLETHYLENEDIAMINE(871-78-3)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: 36/37/38
    3. Safety Statements: 26-36/37/39
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 871-78-3(Hazardous Substances Data)

871-78-3 Usage

Uses

Used in Chemical Industry:
N,N'-DIACETYLETHYLENEDIAMINE is used as a crosslinking agent for enhancing the properties of resins, rubber, and adhesives. Its ability to form chemical bonds between molecules contributes to the improved performance and durability of these materials.
Used in Analytical Chemistry:
N,N'-DIACETYLETHYLENEDIAMINE is used as a chelating agent, playing a crucial role in the analysis and detection of various chemical compounds. Its chelating properties allow for the selective binding and separation of target molecules, facilitating accurate measurements and analyses.
Used in Pharmaceutical Industry:
N,N'-DIACETYLETHYLENEDIAMINE is used in the preparation of pharmaceuticals, where its crosslinking capabilities can be employed to create stable and effective drug formulations. Its role in the synthesis of certain medications highlights its importance in the development of new therapeutic agents.
Used in Textile Industry:
N,N'-DIACETYLETHYLENEDIAMINE is used as a crosslinking agent in textiles, improving the strength, durability, and resistance to environmental factors such as UV radiation and chemical exposure. This enhances the performance and longevity of textile products.
Used in Plastics Industry:
N,N'-DIACETYLETHYLENEDIAMINE is used in the production of plastics to improve their structural integrity and resistance to wear and tear. Its crosslinking properties contribute to the development of high-performance plastic materials for various applications.
Used in Coatings Industry:
N,N'-DIACETYLETHYLENEDIAMINE is used in the formulation of coatings to enhance their adhesion, durability, and resistance to environmental factors. Its crosslinking capabilities improve the overall performance and longevity of coated surfaces.
Safety Precautions:
It is important to handle N,N'-DIACETYLETHYLENEDIAMINE with caution, as it can be toxic if ingested, inhaled, or absorbed through the skin. Proper safety measures, such as wearing protective gear and following handling guidelines, should be strictly adhered to during its use in various applications.

Check Digit Verification of cas no

The CAS Registry Mumber 871-78-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,7 and 1 respectively; the second part has 2 digits, 7 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 871-78:
(5*8)+(4*7)+(3*1)+(2*7)+(1*8)=93
93 % 10 = 3
So 871-78-3 is a valid CAS Registry Number.

871-78-3 Well-known Company Product Price

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  • Alfa Aesar

  • (A11866)  N,N'-Diacetylethylenediamine, 98%   

  • 871-78-3

  • 10g

  • 326.0CNY

  • Detail
  • Alfa Aesar

  • (A11866)  N,N'-Diacetylethylenediamine, 98%   

  • 871-78-3

  • 50g

  • 1381.0CNY

  • Detail

871-78-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name N,N-Diacetylethylenediamine

1.2 Other means of identification

Product number -
Other names N-(2-acetamidoethyl)acetamide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:871-78-3 SDS

871-78-3Synthetic route

acetic anhydride
108-24-7

acetic anhydride

ethylenediamine
107-15-3

ethylenediamine

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Conditions
ConditionsYield
yttria-stabilized zirconia In acetonitrile for 2.5h; Heating;99%
With silica gel for 0.05h; Microwave irradiation; neat (no solvent);98%
With polydopamine sulfamic acid-functionalized silica gel nanocatalyst In neat (no solvent) at 20℃; for 0.2h;96%
2,4,6-triacetyloxy-1,3,5-triazine
13483-16-4

2,4,6-triacetyloxy-1,3,5-triazine

ethylenediamine
107-15-3

ethylenediamine

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Conditions
ConditionsYield
at 25℃; for 0.0833333h; neat (no solvent);99%
1,1,1-trichloroacetone
918-00-3

1,1,1-trichloroacetone

ethylenediamine
107-15-3

ethylenediamine

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Conditions
ConditionsYield
In hexane at 25℃;97%
acetic acid
64-19-7

acetic acid

ethylenediamine
107-15-3

ethylenediamine

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Conditions
ConditionsYield
at 80 - 160℃;93%
In water at 240 - 250℃; for 0.666667h;
With lithium chloride supported solid acid catalyst at 110 - 120℃; for 2h; Temperature; Large scale;
1,8-bis(acetylamino)-3,6-diaza-4,5-dimethyl-3,5-octadiene
137465-85-1

1,8-bis(acetylamino)-3,6-diaza-4,5-dimethyl-3,5-octadiene

A

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

B

1-isocyano-2-(N-acetylamino)-ethane
137465-87-3

1-isocyano-2-(N-acetylamino)-ethane

Conditions
ConditionsYield
With oxygen; rose bengal In acetonitrile at 13℃; for 11h; Irradiation;A 87%
B 87%
ethylenediamine
107-15-3

ethylenediamine

microgel-supported-CH3CO

microgel-supported-CH3CO

A

monoacetylaminoethylamine
1001-53-2

monoacetylaminoethylamine

B

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Conditions
ConditionsYield
In tetrahydrofuran at 25℃; for 14h; Inert atmosphere;A 83.5%
B 9.9%
ethyl acetate
141-78-6

ethyl acetate

ethylenediamine
107-15-3

ethylenediamine

A

monoacetylaminoethylamine
1001-53-2

monoacetylaminoethylamine

B

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Conditions
ConditionsYield
at 100℃; for 36h;A 81%
B n/a
at 20℃; for 6h;A 70%
B n/a
at 20℃;
at 100℃;
acetic acid
64-19-7

acetic acid

ethylenediamine
107-15-3

ethylenediamine

A

lysidine
534-26-9

lysidine

B

monoacetylaminoethylamine
1001-53-2

monoacetylaminoethylamine

C

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Conditions
ConditionsYield
With copper In benzene at 80℃; for 5h;A 74%
B n/a
C n/a
C4H9ClN2O
321746-35-4

C4H9ClN2O

monoacetylaminoethylamine
1001-53-2

monoacetylaminoethylamine

A

1,2-bis(2-acetamidoethyl)-3-(acetamidomethyl)diaziridine
1021441-10-0

1,2-bis(2-acetamidoethyl)-3-(acetamidomethyl)diaziridine

B

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Conditions
ConditionsYield
With potassium carbonate In chloroform at 15℃; under 3750380 Torr; for 48h;A 57%
B n/a
ethylenediamine
107-15-3

ethylenediamine

ethyl 2-acetylacetoacetate
603-69-0

ethyl 2-acetylacetoacetate

A

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

B

ethyl (2Z)-3-[(2-{[(1Z)-3-ethoxy-1-methyl-3-oxoprop-1-enyl]amino}ethyl)amino]but-2-enoate
23652-55-3

ethyl (2Z)-3-[(2-{[(1Z)-3-ethoxy-1-methyl-3-oxoprop-1-enyl]amino}ethyl)amino]but-2-enoate

Conditions
ConditionsYield
In diethyl ether at 20℃;A 48%
B n/a
carbon dioxide
124-38-9

carbon dioxide

ethylenediamine
107-15-3

ethylenediamine

acetonitrile
75-05-8

acetonitrile

A

imidazolidone
120-93-4

imidazolidone

B

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Conditions
ConditionsYield
With ZnO-KF loaded on γ-Al2O3 at 180℃; under 7500.75 Torr; for 4h;A 27%
B n/a
(N-chloromethyl)acetamide
44398-42-7

(N-chloromethyl)acetamide

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Conditions
ConditionsYield
With copper; benzene
1,2-ethanediamine monohydrate
6780-13-8

1,2-ethanediamine monohydrate

acetic anhydride
108-24-7

acetic anhydride

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Conditions
ConditionsYield
Erhitzen bis der Siedepunkt auf 170grad bis 175grad gestiegen ist;
ethyl acetate
141-78-6

ethyl acetate

ethylenediamine
107-15-3

ethylenediamine

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

N-methyl-acetamide
79-16-3

N-methyl-acetamide

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Conditions
ConditionsYield
With di-tert-butyl peroxide
acetamide
60-35-5

acetamide

ethylenediamine
107-15-3

ethylenediamine

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

N-methyl-acetamide
79-16-3

N-methyl-acetamide

A

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

B

N,N'-dimethylsuccinamide
16873-50-0

N,N'-dimethylsuccinamide

C

N-acetyl-β-alanine N'-methylamide
33233-69-1

N-acetyl-β-alanine N'-methylamide

Conditions
ConditionsYield
In solid at -196.1℃; Product distribution; Mechanism; Irradiation; also in aqueous solution;
N,Ν,Ν'-triacetylenediamine
137706-80-0

N,Ν,Ν'-triacetylenediamine

A

peracetic acid
79-21-0

peracetic acid

B

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Conditions
ConditionsYield
With 1,2-ethanediylbistetraphosphonic acid; dihydrogen peroxide at 25℃; Kinetics; Thermodynamic data; various pH values (carbonate buffer), other temperatures; ΔH(excit.), ΔS(excit.);
N,Ν,Ν'-triacetylenediamine
137706-80-0

N,Ν,Ν'-triacetylenediamine

A

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

B

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With water at 25℃; Rate constant; pH 9.60 and 10.47 (carbonate buffer);
acetic anhydride
108-24-7

acetic anhydride

ethylenediamine
107-15-3

ethylenediamine

A

lysidine
534-26-9

lysidine

B

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Conditions
ConditionsYield
A 11 g
B 80 g
acetic acid
64-19-7

acetic acid

ethylenediamine
107-15-3

ethylenediamine

A

1H-imidazole
288-32-4

1H-imidazole

B

lysidine
534-26-9

lysidine

C

2-methylimidazole
693-98-1

2-methylimidazole

D

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Conditions
ConditionsYield
5% platinum on alumina at 280 - 400℃;
5% platinum on alumina at 280 - 400℃; Product distribution; var. catalysts, temp. and contact time;
acetic acid
64-19-7

acetic acid

ethylenediamine
107-15-3

ethylenediamine

A

lysidine
534-26-9

lysidine

B

1,2-dimethyl-1H-imidazole
1739-84-0

1,2-dimethyl-1H-imidazole

C

2-methylimidazole
693-98-1

2-methylimidazole

D

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

E

1-ethyl-2-methyl-4,5-dihydro-1H-imidazole
4814-93-1

1-ethyl-2-methyl-4,5-dihydro-1H-imidazole

Conditions
ConditionsYield
With hydrogen; Pt/Al AP-64K catalyst at 280℃; Product distribution; var. temp. and molar ratio of ragents;
acetic acid
64-19-7

acetic acid

ethylenediamine
107-15-3

ethylenediamine

A

lysidine
534-26-9

lysidine

B

1-ethyl-2-methylimidazole
21202-52-8

1-ethyl-2-methylimidazole

C

2-methylimidazole
693-98-1

2-methylimidazole

D

monoacetylaminoethylamine
1001-53-2

monoacetylaminoethylamine

E

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

F

1-ethyl-2-methyl-4,5-dihydro-1H-imidazole
4814-93-1

1-ethyl-2-methyl-4,5-dihydro-1H-imidazole

Conditions
ConditionsYield
Pt/Al2O3 at 300 - 400℃; Product distribution; other ratios of reactants;
acetic acid
64-19-7

acetic acid

ethylenediamine
107-15-3

ethylenediamine

A

lysidine
534-26-9

lysidine

B

2-methylimidazole
693-98-1

2-methylimidazole

C

monoacetylaminoethylamine
1001-53-2

monoacetylaminoethylamine

D

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Conditions
ConditionsYield
γ-Al2O3 at 330℃; for 0.4h; Product distribution; var. temp. and contact time;
N,N,N',N'-tetraacetylethylenediamine
10543-57-4

N,N,N',N'-tetraacetylethylenediamine

A

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

B

N,Ν,Ν'-triacetylenediamine
137706-80-0

N,Ν,Ν'-triacetylenediamine

Conditions
ConditionsYield
With iron(III) perchlorate In water at 20℃; for 480h; pH=2.9 - 5.5; Kinetics; Hydrolysis;
Isopropenyl acetate
108-22-5

Isopropenyl acetate

ethylenediamine
107-15-3

ethylenediamine

A

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

B

N-acetyl-ethylenediamine

N-acetyl-ethylenediamine

Conditions
ConditionsYield
With water
N,Ν,Ν'-triacetylenediamine
137706-80-0

N,Ν,Ν'-triacetylenediamine

acetic acid
64-19-7

acetic acid

A

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

B

acetic anhydride
108-24-7

acetic anhydride

Conditions
ConditionsYield
at 140℃; Kinetics; Temperature;
tetra-acetylenediamine

tetra-acetylenediamine

A

peracetic acid
79-21-0

peracetic acid

B

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Conditions
ConditionsYield
With water; dihydrogen peroxide at 20℃;
N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

acetic anhydride
108-24-7

acetic anhydride

N,Ν,Ν'-triacetylenediamine
137706-80-0

N,Ν,Ν'-triacetylenediamine

Conditions
ConditionsYield
at 125℃; for 3h; Temperature;99.62%
N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

tetra-acetylethylenediamine

tetra-acetylethylenediamine

Conditions
ConditionsYield
With acetic anhydride98%
With acetic anhydride
With acetic anhydride
With acetic anhydride
N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

acetic anhydride
108-24-7

acetic anhydride

ethylenediamine tetraacetic acid
117659-76-4

ethylenediamine tetraacetic acid

Conditions
ConditionsYield
With lithium chloride supported solid acid catalyst at 130 - 140℃; for 3h; Temperature; Large scale;93.41%
Glyoxal
131543-46-9

Glyoxal

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

1,4-diacetylpiperazine-2,3-diol
960507-67-9

1,4-diacetylpiperazine-2,3-diol

Conditions
ConditionsYield
With sodium carbonate In water at 20℃; pH=8 - 9;90%
cobalt(II) bromide hydrate

cobalt(II) bromide hydrate

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Co(2+)*2CH3CONH(CH2)2NHCOCH3*2Br(1-)*2H2O=[Co(CH3CONH(CH2)2NHCOCH3)2(H2O)2]Br2

Co(2+)*2CH3CONH(CH2)2NHCOCH3*2Br(1-)*2H2O=[Co(CH3CONH(CH2)2NHCOCH3)2(H2O)2]Br2

Conditions
ConditionsYield
With 2,2-dimethoxypropane In acetonitrile 2 equiv. of ligand, 10 vol % dimethoxypropane in MeCN; slow concn.; elem. anal.;83%
N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

acetic anhydride
108-24-7

acetic anhydride

N,N,N',N'-tetraacetylethylenediamine
10543-57-4

N,N,N',N'-tetraacetylethylenediamine

Conditions
ConditionsYield
With solid acid SO4(2-)/Al2O3 at 110 - 160℃; for 4.5h; Reagent/catalyst; Temperature;81.9%
manganese(II) bromide tetrahydrate

manganese(II) bromide tetrahydrate

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Mn(2+)*3CH3CONH(CH2)2NHCOCH3*2Br(1-)*H2O=Mn(CH3CONH(CH2)2NHCOCH3)3Br2*H2O

Mn(2+)*3CH3CONH(CH2)2NHCOCH3*2Br(1-)*H2O=Mn(CH3CONH(CH2)2NHCOCH3)3Br2*H2O

Conditions
ConditionsYield
With 2,2-dimethoxypropane In acetonitrile 2 equiv. of ligand, 10 vol % dimethoxypropane in MeCN; slow concn.; elem. anal.;79%
nickel(II) nitrate hydrate

nickel(II) nitrate hydrate

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Ni(2+)*2CH3CONH(CH2)2NHCOCH3*2NO3(1-)*3H2O=Ni(CH3CONH(CH2)2NHCOCH3)2(NO3)2*3H2O

Ni(2+)*2CH3CONH(CH2)2NHCOCH3*2NO3(1-)*3H2O=Ni(CH3CONH(CH2)2NHCOCH3)2(NO3)2*3H2O

Conditions
ConditionsYield
In methanol; acetonitrile mixing hot solns. of metal nitrate (in MeOH) with 2 equiv. ligand (in MeCN); sepn. of oil; trituration with Et2O; elem. anal.;79%
cobalt(II) nitrate hexahydrate

cobalt(II) nitrate hexahydrate

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

Co(2+)*2CH3CONH(CH2)2NHCOCH3*2NO3(1-)*2H2O=Co(CH3CONH(CH2)2NHCOCH3)2(NO3)2*2H2O

Co(2+)*2CH3CONH(CH2)2NHCOCH3*2NO3(1-)*2H2O=Co(CH3CONH(CH2)2NHCOCH3)2(NO3)2*2H2O

Conditions
ConditionsYield
In methanol; acetonitrile mixing hot solns. of metal nitrate (in MeOH) with 2 equiv. ligand (in MeCN); sepn. of oil; trituration with Et2O; elem. anal.;76%
N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

nickel dibromide

nickel dibromide

Ni(2+)*2CH3CONH(CH2)2NHCOCH3*2Br(1-)*2H2O=Ni(CH3CONH(CH2)2NHCOCH3)2Br2*2H2O

Ni(2+)*2CH3CONH(CH2)2NHCOCH3*2Br(1-)*2H2O=Ni(CH3CONH(CH2)2NHCOCH3)2Br2*2H2O

Conditions
ConditionsYield
With 2,2-dimethoxypropane In acetonitrile 2 equiv. of ligand, 10 vol % dimethoxypropane in MeCN; slow concn.; elem. anal.;66%
diethyl 1,4-cyclohexanedione-2,5-dicarboxylate
787-07-5

diethyl 1,4-cyclohexanedione-2,5-dicarboxylate

N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

2,5-bis-(2-acetylamino-ethylamino)-terephthalic acid diethyl ester
102314-88-5

2,5-bis-(2-acetylamino-ethylamino)-terephthalic acid diethyl ester

Conditions
ConditionsYield
anschliessend Behandeln mit Jod in Aethanol;
N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

lysidine
534-26-9

lysidine

Conditions
ConditionsYield
With magnesium
With calcium oxide at 220 - 265℃; for 2h; Yield given;
With calcium oxide at 210 - 220℃; for 2h;
N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

N,N'-diethylethylenediamine
111-74-0

N,N'-diethylethylenediamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether
N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

but-3-ene-1,2-diamine
73314-67-7

but-3-ene-1,2-diamine

Conditions
ConditionsYield
bei der Destillation, teilweise;
N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

N',N'''-diphenyl-N,N''-ethanediyl-bis-acetamidine

N',N'''-diphenyl-N,N''-ethanediyl-bis-acetamidine

Conditions
ConditionsYield
With phosphorus pentachloride; benzene beim Erwaermen anschliessend mit Anilin;
N,N'-diacetylethylenediamine
871-78-3

N,N'-diacetylethylenediamine

N',N'''-bis-(4-ethoxy-phenyl)-N,N''-ethanediyl-bis-acetamidine

N',N'''-bis-(4-ethoxy-phenyl)-N,N''-ethanediyl-bis-acetamidine

Conditions
ConditionsYield
aufeinanderfolgenden Umsetzen mit PCl5 und mit p-Phenetidin;

871-78-3Relevant articles and documents

Near-Ambient-Temperature Dehydrogenative Synthesis of the Amide Bond: Mechanistic Insight and Applications

Kar, Sayan,Xie, Yinjun,Zhou, Quan Quan,Diskin-Posner, Yael,Ben-David, Yehoshoa,Milstein, David

, p. 7383 - 7393 (2021/06/30)

The current existing methods for the amide bond synthesis via acceptorless dehydrogenative coupling of amines and alcohols all require high reaction temperatures for effective catalysis, typically involving reflux in toluene, limiting their potential practical applications. Herein, we report a system for this reaction that proceeds under mild conditions (reflux in diethyl ether, boiling point 34.6 °C) using ruthenium PNNH complexes. The low-temperature activity stems from the ability of Ru-PNNH complexes to activate alcohol and hemiaminals at near-ambient temperatures through the assistance of the terminal N-H proton. Mechanistic studies reveal the presence of an unexpected aldehyde-bound ruthenium species during the reaction, which is also the catalytic resting state. We further utilize the low-temperature activity to synthesize several simple amide bond-containing commercially available pharmaceutical drugs from the corresponding amines and alcohols via the dehydrogenative coupling method.

Rational design of bifunctional catalyst from KF and ZnO combination on alumina for cyclic urea synthesis from CO2 and diamine

John, Crowny,Kulal, Nagendra,Shanbhag, Ganapati V.

, (2020/04/22)

This study is mainly focused on the design of stable, active and selective catalyst for direct synthesis of 2-imidazolidinone (cyclic urea) from ethylenediamine and CO2. Based on the rationale for the catalyst properties needed for this reaction, KF, ZnO and Al2O3 combination was selected to design the catalyst. ZnO/KF/Al2O3 catalyst was prepared by stepwise wet-impregnation followed by the removal of physisorbed KF from the surface. High product yield could be achieved by tuning acid-base sites by varying the composition and calcination temperature. The catalysts were characterized by various techniques like XRD, N2-sorption, NH3-TPD, CO2-TPD, TEM, XPS and FT-IR measurements. It is shown that acidic and basic properties of the solvent can influence the activity and product selectivity for this reaction. Under optimized condition; 180 °C, 10 bar and 10 wt.% catalyst in batch mode, 96.3 % conversion and 89.6 % selectivity towards the 2-imidazolidinone were achieved.

Fe3O4@PEG core/shell nanoparticles as magnetic nanocatalyst for acetylation of amines and alcohols using ultrasound irradiations under solvent-free conditions

Veisi, Hojat,Nikseresht, Ahmad,Rostami, Afsaneh,Hemmati, Saba

, p. 507 - 520 (2018/10/24)

Abstract: Ultrasound irradiation was used to prepare one-pot Fe3O4@PEG core/shell nanostructure for the first time. The morphology, structure, and physicochemical properties were specified by different analytical techniques including field emission scanning electron microscopy, Fourier transform infrared spectroscopy, energy-dispersive X-ray spectroscopy, transmission electron microscopy, X-ray powder diffraction, and vibrating sample magnetometer. For acetylation of phenols, alcohols, and amines, the synthesized Fe3O4@PEG core/shell nanoparticles were used as an efficient heterogeneous and green catalyst with acetic anhydride under sonication applying mild reaction conditions. Different electron-withdrawing and electron-donating substrates indicate a prominent yield of desired products with the merit of reusability of Fe3O4@PEG nanocatalyst and magnetic separation. Graphical Abstract: [Figure not available: see fulltext.].

Method for catalytic synthesis of tetraacetylethylenediamine by utilizing supported lithium chloride

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Paragraph 0015; 0017; 0018; 0020; 0022; 0023, (2019/08/20)

The invention provides a method for catalytic synthesis of tetraacetylethylenediamine by utilizing supported lithium chloride. Specifically, the method comprises the following steps: (1) sufficientlymixing a lithium chloride solution, a grinding aid dispersant and a carrier under stirring at room temperature, performing high-temperature drying, and performing grinding to obtain the supported lithium chloride solid acid catalyst; (2) quickly adding anhydrous acetic acid dropwise into ethylenediamine and a conventional catalyst; performing heating, performing a heat preservation reaction, and separating water; and adding acetic anhydride and the lithium chloride catalyst, continuing heating, and performing a reaction; and (3) performing cooling, performing crystallization, performing washing, and performing drying to obtain the tetraacetylethylenediamine. The method provided by the invention utilizes the supported lithium chloride solid acid to catalyze the synthesis of the tetraacetylethylenediamine by the ethylenediamine and an acylating reagent, and the catalyst is beneficial for recovering and can be recycled and has less pollution to the environment; the catalytic efficiency ishigh, the reaction time is effectively shortened, and the product yield can reach 90% or more; and the preparation method of the catalyst is simple, has low costs, and facilitates realizing industrial production and application of the tetraacetylethylenediamine.

Preparation of Polydopamine Sulfamic Acid-Functionalized Silica Gel as Heterogeneous and Recyclable Nanocatalyst for Acetylation of Alcohols and Amines Under Solvent-Free Conditions

Veisi, Hojat,Vafajoo, Saba,Bahrami, Kiumars,Mozafari, Bita

, p. 2734 - 2745 (2018/07/30)

To fabricate SiO2/PDA–SO3H nanocatalyst, a suitable method is designed for the loading of sulfonic acid groups on the surface of polydopamine (PDA)-encapsulated SiO2 nanoparticles. To bridge the gap between heterogeneous and homogeneous catalysis, surface functionalization of silica gel is an elegant procedure. The morphology, structure, and physicochemical features were specified using different analytical techniques including field emission scanning electron microscopy (FESEM), Fourier transformed infrared spectroscopy (FT-IR), high resolution-transmission electron microscopy (HR-TEM), energy dispersive X-ray spectroscopy (EDS), wavelength-dispersive X-ray spectroscopy (WDX), X-ray photoelectron spectroscopy (XPS), and back titration. The SiO2/PDA–SO3H nanoparticles are efficient nanocatalysts for the acetylation of many alcohols, phenols, and amines with acetic anhydride under solvent-free conditions in good to excellent yields. Moreover, the reuse and recovery of the catalyst was shown seven times without detectible loss in activity. Graphical Abstract: [Figure not available: see fulltext.]

Anodic oxidation of bisamides from diaminoalkanes by constant current electrolysis

Golub, Tatiana,Becker, James Y.

, p. 861 - 868 (2018/04/30)

In general, bisamides derived from diamines and involving 3 and 4 methylene groups as spacers between the two amide functionalities behave similar to monoamides upon anodic oxidation in methanol/LiClO4 because both types undergo majorly mono- and dimethoxylations at the α-position to the N atom. However, in cases where the spacer contains two methylene groups only the anodic process leads mostly to CH2-CH2 bond cleavage to afford products of type RCONHCH2OCH3. Moreover, upon replacing LiClO4 with Et4NBF4 an additional fragmentation type of product was generated from the latter amides, namely RCONHCHO. Also, the anodic process was found to be more efficient with C felt as the anode, and in a mixture of 1:1 methanol/acetonitrile co-solvents.

Simple and Versatile Laboratory Scale CSTR for Multiphasic Continuous-Flow Chemistry and Long Residence Times

Chapman, Michael R.,Kwan, Maria H. T.,King, Georgina,Jolley, Katherine E.,Hussain, Mariam,Hussain, Shahed,Salama, Ibrahim E.,González Nino, Carlos,Thompson, Lisa A.,Bayana, Mary E.,Clayton, Adam D.,Nguyen, Bao N.,Turner, Nicholas J.,Kapur, Nikil,Blacker, A. John

, p. 1294 - 1301 (2017/09/23)

A universal multistage cascade CSTR has been developed that is suitable for a wide range of continuous-flow processes. Coined by our group the "Freactor" (free-to-access reactor), the new reactor integrates the efficiency of pipe-flow processing with the advanced mixing of a CSTR, delivering a general "plug-and-play" reactor platform which is well-suited to multiphasic continuous-flow chemistry. Importantly, the reactor geometry is easily customized to accommodate reactions requiring long residence times (≥3 h tested).

Four b acyl radicals alkane diamine method for manufacturing

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Page/Page column 11, (2017/05/12)

The present invention relates to a preparation method for tetraacetyl alkylene diamine, characterized in that tetraacetyl alkylene diamine is prepared by carrying out an acylation reaction of a diacetyl alkylene diamine and a carboxylic anhydride under the catalysis of a solid acidic catalyst.

Amide exchange reaction: A simple and efficient CuO catalyst for diacetamide synthesis

Li, Qinghe,Wang, Peixue,Deng, Youquan

, p. 40890 - 40894 (2016/05/19)

A highly copper-catalysed amide exchange reaction of hexamethylenediamine (HDA) with CH3CN and H2O for the synthesis of hexamethylenebisacetamide (HMBA) without an organic solvent or gas protection was developed. 100% HDA conversion and >99% HMBA selectivity was obtained. X-ray diffraction, scanning emission microscopy, and temperature-programmed reduction of hydrogen were used to characterize the structural properties of the catalyst. The reaction mechanism was also investigated.

Colloid and nanosized catalysts in organic synthesis: XIII. Synthesis of 2-R-2-imidazolines catalyzed by copper and iron oxide nanoparticles

Popov,Mokhov,Kalitina

, p. 281 - 285 (2016/04/20)

The reaction of carboxylic acids with ethylenediamine catalyzed by copper or iron oxide nanoparticles proceeds at 80°C with azeotropic water distilling off during 2-8 h to form 2-R-2-imidazolines. Acyl and diacyl derivatives of ethylenediamine are formed in the reaction as side products.

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