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  • 619-50-1 Structure
  • Basic information

    1. Product Name: Methyl 4-nitrobenzoate
    2. Synonyms: p-carbomethoxynitrobenzene;p-Nitrobenzoic acid methyl ester;p-nitrobenzoicacidmethylester;p-nitro-benzoicacimethylester;Methyl 4-nitrobenzoate/4-Nitrobenzoic acid methyl ester;Methyl DL-p-Hydroxyphenylglycine;METHYL 4-NITROBENZOATE, 99+%;BENZOICACID,PARA-NITRO-,METHYLESTER
    3. CAS NO:619-50-1
    4. Molecular Formula: C8H7NO4
    5. Molecular Weight: 181.15
    6. EINECS: 210-599-2
    7. Product Categories: Aromatic Esters;C8 to C9;Carbonyl Compounds;Esters;Building Blocks;C8 to C9;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
    8. Mol File: 619-50-1.mol
    9. Article Data: 389
  • Chemical Properties

    1. Melting Point: 94-96 °C(lit.)
    2. Boiling Point: 314.24°C (rough estimate)
    3. Flash Point: 94-96°C
    4. Appearance: light yellow to yellow fine crystalline powder
    5. Density: 1.4283 (rough estimate)
    6. Vapor Pressure: 4.19E-06mmHg at 25°C
    7. Refractive Index: 1.5468 (estimate)
    8. Storage Temp.: Store below +30°C.
    9. Solubility: Solubility in methanol is almost transparent.
    10. BRN: 1912198
    11. CAS DataBase Reference: Methyl 4-nitrobenzoate(CAS DataBase Reference)
    12. NIST Chemistry Reference: Methyl 4-nitrobenzoate(619-50-1)
    13. EPA Substance Registry System: Methyl 4-nitrobenzoate(619-50-1)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: 22-24/25
    4. WGK Germany: 3
    5. RTECS: DH5775000
    6. TSCA: Yes
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 619-50-1(Hazardous Substances Data)

619-50-1 Usage

Description

Methyl 4-nitrobenzoate is an organic compound with the chemical formula C8H7NO4. It is a derivative of benzoic acid, where a nitro group is attached to the 4-position and a methyl group is attached to the ester. It is a yellow crystalline solid and is soluble in organic solvents.

Uses

Used in Biochemical Characterization:
Methyl 4-nitrobenzoate is used as a substrate in the biochemical characterization of NfsA, the Escherichia coli major nitroreductase enzyme. This enzyme exhibits a high amino acid sequence homology to Frp, a Vibrio harveyi flavin oxidoreductase. The use of Methyl 4-nitrobenzoate helps in understanding the enzyme's activity, specificity, and mechanism of action in the reduction of nitro compounds.

Purification Methods

Dissolve the benzoate in diethyl ether, then wash it with aqueous alkali; the ether is evaporated and the ester is recrystallised from EtOH. [Beilstein 9 H 390, 9 IV 1074.]

Check Digit Verification of cas no

The CAS Registry Mumber 619-50-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 9 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 619-50:
(5*6)+(4*1)+(3*9)+(2*5)+(1*0)=71
71 % 10 = 1
So 619-50-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H7NO4/c1-5-4-6(9(12)13)2-3-7(5)8(10)11/h2-4H,1H3,(H,10,11)/p-1

619-50-1 Well-known Company Product Price

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  • Alfa Aesar

  • (A12928)  Methyl 4-nitrobenzoate, 99%   

  • 619-50-1

  • 100g

  • 386.0CNY

  • Detail
  • Alfa Aesar

  • (A12928)  Methyl 4-nitrobenzoate, 99%   

  • 619-50-1

  • 500g

  • 1549.0CNY

  • Detail
  • Alfa Aesar

  • (A12928)  Methyl 4-nitrobenzoate, 99%   

  • 619-50-1

  • 2500g

  • 6184.0CNY

  • Detail

619-50-1SDS

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 Methyl 4-nitrobenzoate

1.2 Other means of identification

Product number -
Other names p-Nitrobenzoic acid methyl ester

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:619-50-1 SDS

619-50-1Synthetic route

methanol
67-56-1

methanol

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With dmap; 2-chloro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluorododecyl)pyridinium trifluoromethanesulfonate; triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;100%
Stage #1: 4-nitro-benzoic acid With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 20℃; for 0.0833333h; Garegg-Samuelsson type reaction;
Stage #2: methanol In dichloromethane at 20℃; Garegg-Samuelsson type reaction;
100%
With dmap; 2-chloro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluorododecyl)pyridinium trifluoromethanesulfonate; triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;100%
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

carbon monoxide
201230-82-2

carbon monoxide

triethylmethoxystannane
1067-21-6

triethylmethoxystannane

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With iodophenylbis(triphenylphosphine)palladium under 760 Torr; for 1h;100%
diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
In methanol; toluene at 20℃; for 2h;100%
In ethyl acetate60%
In methanol; diethyl ether; hexane at 20℃; for 2h; Inert atmosphere;178 mg
1-(dimethoxymethyl)pyrrolidine
5564-73-8

1-(dimethoxymethyl)pyrrolidine

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 30℃; for 25h;100%
methanol
67-56-1

methanol

diethyl N-(4-nitrobenzoyloxy)-4-fluorobenzimidoylphosphonate

diethyl N-(4-nitrobenzoyloxy)-4-fluorobenzimidoylphosphonate

A

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

B

diethyl [N-(hydroxy)imino](p-fluorophenyl)methylphosphonate
154109-07-6

diethyl [N-(hydroxy)imino](p-fluorophenyl)methylphosphonate

Conditions
ConditionsYield
for 6h; Inert atmosphere; Reflux;A 100%
B 100%
methanol
67-56-1

methanol

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With water; iodine; sodium nitrite at 20 - 70℃; chemoselective reaction;99%
With ammonium peroxydisulfate at 60℃; for 2.5h;99%
With potassium hydroxide; iodine at 0℃; for 0.0166667h;98%
methanol
67-56-1

methanol

4-nitrobenzyl chloride
619-73-8

4-nitrobenzyl chloride

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With sodium carbonate; palladium; silver(l) oxide at 80℃; for 48h; Molecular sieve;99%
With dihydrogen peroxide for 3h; Irradiation;95%
With oxygen; potassium carbonate at 60℃; under 750.075 Torr; for 20h;94%
methanol
67-56-1

methanol

ethyl 4-nitrobenzoate
99-77-4

ethyl 4-nitrobenzoate

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
scandium tris(trifluoromethanesulfonate) at 64℃; for 168h;98%
With dipotassium hydrogenphosphate for 5h; Reflux;98%
With potassium ethoxide
acrylonitrile; triphenylphosphine at 25℃; for 24h;71 % Chromat.
N,N-dimethoxyamine
88470-26-2

N,N-dimethoxyamine

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
In benzene for 3h; Heating;98%
In benzene Product distribution; Mechanism; Heating; other nucleophiles; var. reaction conditions;98%
In benzene for 3h; Mechanism; Heating;98%
dimethyl dicarbonate
4525-33-1

dimethyl dicarbonate

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
magnesium(II) perchlorate In nitromethane at 40℃; for 16h;98%
With 2,6-dimethylpyridine; fac-tris(2-phenylpyridinato-N,C2')iridium(III) In N,N-dimethyl-formamide at 20℃; for 48h; Sealed tube; Inert atmosphere; Irradiation;
methanol
67-56-1

methanol

p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

carbon monoxide
201230-82-2

carbon monoxide

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane In N,N-dimethyl-formamide at 80℃; under 2327.23 Torr;98%
With triethylamine at 100℃; under 3750.38 Torr; for 1.5h; Inert atmosphere;95%
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; under 5250.53 Torr; continuous flow reactor;81%
N-methyl-N-nitrosotoluene-p-sulfonamide
80-11-5

N-methyl-N-nitrosotoluene-p-sulfonamide

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran; methanol; water at 20℃;98%
Stage #1: N-methyl-N-nitrosotoluene-p-sulfonamide With potassium hydroxide In methanol; water; N,N-dimethyl-formamide Flow reactor;
Stage #2: 4-nitro-benzoic acid In methanol; diethyl ether; water; N,N-dimethyl-formamide at 0 - 25℃; Sonication;
90%
methanol
67-56-1

methanol

N-amino-(4-nitrophenyl)carboxamide
636-97-5

N-amino-(4-nitrophenyl)carboxamide

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate at 20℃; for 0.25h; Esterification;97%
With Oxone at 20℃; for 6h; oxidative esterification;84%
poly(p-methyltriazenestyrene)

poly(p-methyltriazenestyrene)

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
In 1,2-dimethoxyethane for 16h;97%
methyl chloroformate
79-22-1

methyl chloroformate

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With dmap; triethylamine In acetonitrile97%
tetramethylorthosilicate
681-84-5

tetramethylorthosilicate

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; (t-Bu2POH)2PdCl2 In acetonitrile at 50℃; for 24h;97%
phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With diethylazodicarboxylate In tetrahydrofuran for 2h;96%
With diethylazodicarboxylate In tetrahydrofuran for 2h; Mechanism; other phosphite, other carboxylic acid, phenols, imides and C-H acids;92%
methanol
67-56-1

methanol

formaldehyd
50-00-0

formaldehyd

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

A

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

B

bis-1,5(4-nitrophenyl)-1,5-pentanedione
21600-84-0

bis-1,5(4-nitrophenyl)-1,5-pentanedione

Conditions
ConditionsYield
hydroxocobalt(III) Schiff base at 60℃; for 1.5h; Product distribution; Mechanism; var. 4-subst. educts; var. reaction conditions;A 92%
B 96%
methanol
67-56-1

methanol

1-(4-nitrophenyl)propan-1-one
3758-70-1

1-(4-nitrophenyl)propan-1-one

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With N,N-dimethyl-formamide dimethyl acetal for 16h; Heating;95%
methyl 2-hydroxy-5-nitrobenzoate
17302-46-4

methyl 2-hydroxy-5-nitrobenzoate

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

A

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

B

5-nitrosalicylic acid
96-97-9

5-nitrosalicylic acid

Conditions
ConditionsYield
Stage #1: 4-nitro-benzoic acid With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 0.5h;
Stage #2: methyl 2-hydroxy-5-nitrobenzoate at 110℃; for 24h; Temperature;
A 95%
B n/a
methanol
67-56-1

methanol

N,N-(Boc)2-4-nitrobenzamide

N,N-(Boc)2-4-nitrobenzamide

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With C26H28N3O3S(1+)*F6P(1-); nickel diacetate; potassium carbonate; triethylamine at 25℃; for 2h;95%
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid at 80 - 85℃; for 9.5h; Neat (no solvent);94.2%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 0.0180556h; microwave irradiation;90%
With potassium carbonate In dimethyl sulfoxide at 90℃; for 16h; Inert atmosphere; Green chemistry;86%
methanol
67-56-1

methanol

4-nitro-benzoyl chloride
122-04-3

4-nitro-benzoyl chloride

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane for 0.166667h;94%
With pyridine at 70℃; for 3h;91%
at 25℃; Thermodynamic data; ΔH;
benzyl alcohol
100-51-6

benzyl alcohol

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride at 20℃; for 2.5h; Esterification;94%
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane In N,N-dimethyl-formamide at 80℃; under 2327.23 Torr;94%
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; under 11251.1 Torr; continuous flow reactor;77%
With palladium diacetate; triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; hydrazine In tetrahydrofuran; 1,4-dioxane at 100℃; under 11251.1 Torr; Temperature; Flow reactor;77%
With ruthenium(III) trichloride hydrate; 1,4-bis(2'-diphenylphosphino-3'-methylimidazolium)butane triflate; triethylamine In 1-methyl-pyrrolidin-2-one at 140℃; under 15001.5 Torr; for 16h; Autoclave;80 %Chromat.
methanol
67-56-1

methanol

1-(4-nitrophenyl)-3-phenyl-1-propanone
54914-77-1

1-(4-nitrophenyl)-3-phenyl-1-propanone

A

3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

B

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With N,N-dimethyl-formamide dimethyl acetal for 16h; Heating;A n/a
B 93%
4-nitrobenzyl chloride
619-73-8

4-nitrobenzyl chloride

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: 4-nitrobenzyl chloride With sodium chlorite; sodium dihydrogenphosphate; Me-AZADO+Cl- In dichloromethane; water at 25℃; for 1.5h;
Stage #2: With 2-methyl-but-2-ene In dichloromethane; water
Stage #3: diazomethane With hydrogenchloride; sodium hydroxide Product distribution / selectivity; more than 3 stages;
93%
Stage #1: 4-nitrobenzyl chloride With sodium chlorite; sodium dihydrogenphosphate; 2,2,6,6-tetramethylpiperidin-1-oxoammonium chloride In dichloromethane; water at 25℃; for 1.5h;
Stage #2: With 2-methyl-but-2-ene In dichloromethane; water
Stage #3: diazomethane With hydrogenchloride; sodium hydroxide Product distribution / selectivity; more than 3 stages;
63%
4-methoxycarbonylphenylboronic acid
99768-12-4

4-methoxycarbonylphenylboronic acid

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol; N–nitrosaccharin at 60℃; for 19h; Reagent/catalyst; Inert atmosphere; Schlenk technique;93%
With Iron(III) nitrate nonahydrate In toluene at 80℃; for 18h; Inert atmosphere;86%
With dipotassium peroxodisulfate; bismuth (III) nitrate pentahydrate In benzene at 70℃; for 12h; Inert atmosphere;74%
With copper(I) oxide; tetrabutylammonium nitrite In acetonitrile at 20℃;53%
methanol
67-56-1

methanol

N-(4-nitrobenzoyl)oxazolidinone
25393-54-8

N-(4-nitrobenzoyl)oxazolidinone

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With [t-Bu2SnCl(OH)]2 In toluene at 85℃; for 14h;92%
ethanol
64-17-5

ethanol

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

ethyl 4-nitrobenzoate
99-77-4

ethyl 4-nitrobenzoate

Conditions
ConditionsYield
With tert-butylamine for 10h; Heating;100%
Stage #1: ethanol With platinum(IV) oxide; hydrogen at 60℃; under 750.075 - 1500.15 Torr; for 2h; Autoclave; Green chemistry;
Stage #2: 4-nitrobenzoic acid methyl ester at 60℃; Autoclave; Inert atmosphere; Green chemistry; chemoselective reaction;
93%
With dichlorobis(1-butylimidazolium) zinc at 70 - 80℃;93%
4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

N-[(4-methoxycarbonyl)phenyl]hydroxylamine
24226-29-7

N-[(4-methoxycarbonyl)phenyl]hydroxylamine

Conditions
ConditionsYield
With 5% rhodium-on-charcoal; hydrazine hydrate In tetrahydrofuran at 0℃; for 5h; Inert atmosphere;100%
With 5% rhodium-on-charcoal; hydrazine hydrate In tetrahydrofuran at 0℃; Inert atmosphere;100%
With rhodium contaminated with carbon; hydrazine hydrate In tetrahydrofuran at 0℃; for 5h; Inert atmosphere;100%
4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

4-methoxycarbonyl aniline
619-45-4

4-methoxycarbonyl aniline

Conditions
ConditionsYield
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran; water at 20℃; for 0.5h;100%
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.5h;100%
With sodium tetrahydroborate; water In ethanol at 25℃; for 1h; Solvent; chemoselective reaction;100%
4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

acetonitrile
75-05-8

acetonitrile

methyl 4-(ethylamino)benzoate
79663-14-2

methyl 4-(ethylamino)benzoate

Conditions
ConditionsYield
With palladium 10% on activated carbon; ammonium acetate; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;100%
4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With AlBrCl3(1-)*C5H5N*H(1+) at 140℃; for 3h;99%
With methanesulfonic acid; 1-methylimidazolium hydrobromide at 120℃; for 2h;96%
With iron(III) sulfate; water In toluene at 110℃; for 4h; Ionic liquid;95%
4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

benzyl alcohol
100-51-6

benzyl alcohol

benzyl 4-nitrobenzoate
14786-27-7

benzyl 4-nitrobenzoate

Conditions
ConditionsYield
With lanthanum(III) nitrate hexahydrate; TOP at 110℃; for 5h; Reagent/catalyst; Molecular sieve;99%
With N,N'-biscyclohexyl-imidazol-2-ylidene; 4 A molecular sieve In tetrahydrofuran at 20℃; for 0.25h;96%
1,3-dicyclohexyl-imidazol-2-ylidene In tetrahydrofuran at 20℃; for 0.25h;96%
1-octadecanol
112-92-5

1-octadecanol

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

octadecyl 4-nitro-benzoate
56426-96-1

octadecyl 4-nitro-benzoate

Conditions
ConditionsYield
Stage #1: 1-octadecanol; 4-nitrobenzoic acid methyl ester In xylene for 0.5h; Heating;
Stage #2: With TiO(acac)2 In xylene for 4.5h; Heating;
99%
1.3-propanedithiol
109-80-8

1.3-propanedithiol

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

1,3-di(4-methoxycarbonylphenylthio)propane

1,3-di(4-methoxycarbonylphenylthio)propane

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 25℃; for 1.5h;99%
With magnesium methanolate In N,N-dimethyl-formamide at 80℃; for 8h;78%
4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

butan-1-ol
71-36-3

butan-1-ol

butyl p-nitrobenzoate
120-48-9

butyl p-nitrobenzoate

Conditions
ConditionsYield
With Zn4(OCOCF3)6O In di-isopropyl ether for 40h; Heating;99%
4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

hexan-1-ol
111-27-3

hexan-1-ol

4-nitrophenyl hexanoate
6268-24-2

4-nitrophenyl hexanoate

Conditions
ConditionsYield
With tetrabutylammonium acetate; oxiranyl-methanol In hexane for 2h; Reflux;99%
4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

dimethyl 4,4'-azoxydibenzoate
23663-92-5

dimethyl 4,4'-azoxydibenzoate

Conditions
ConditionsYield
With potassium hydroxide In water; isopropyl alcohol at 30℃; under 760.051 Torr; for 10h; Inert atmosphere;98%
With manganese; acetic acid In tetrahydrofuran; water at 20℃; for 15h;70%
With triethylsilane; indium(III) bromide In N,N-dimethyl-formamide at 60℃; for 12h;64%
With bismuth; sodium hydroxide; sodium tetrahydroborate; oxygen 1.) methanol, room temperature, 0.5 h, 2.) methanol, room temperate, 4 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1: 78 percent / Sb, NaBH4 / methanol / 1 h / Ambient temperature
2: 88 percent / NaOH, O2 / 4 h / Ambient temperature
View Scheme
4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

propan-1-ol-3-amine
156-87-6

propan-1-ol-3-amine

N-(3-Hydroxy-propyl)-4-nitro-benzamid
90690-76-9

N-(3-Hydroxy-propyl)-4-nitro-benzamid

Conditions
ConditionsYield
With ammonium nitrate In neat (no solvent) at 20℃; for 12h; Green chemistry;98%
In toluene at 97℃; for 4h; Acylation;79%
4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

N,N-diethylethylenediamine
100-36-7

N,N-diethylethylenediamine

N-(2-(diethylamino)ethyl)-4-nitrobenzamide
1664-52-4

N-(2-(diethylamino)ethyl)-4-nitrobenzamide

Conditions
ConditionsYield
With ammonium nitrate In neat (no solvent) at 20℃; for 12h; Green chemistry;98%
4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

4-nitrobenzamide
619-80-7

4-nitrobenzamide

Conditions
ConditionsYield
With ammonia In methanol at 70℃;98%

619-50-1Relevant articles and documents

Selective Complexation of Hydrazone Based Ketimine with 3d, 4d, and 5d Metals: Synthesis, Characterization, and Biological Activity

Ahmad,Taj,Tirmizi,Alelwani,Hajjar,Makki,Shah,Ali,Hassan,Tahir,Siddiq

, p. 142 - 147 (2019)

The hydrazone derived ketimine of dehydroacetic acid and its metal {Cu(II), Ni(II), Zn(II), Fe(III), Cd(II), Pd(II), La(III), Nd(III), Ce(III)} complexes are synthesized and characterized by IR, 1H and 13C NMR, and UV-Vis spectroscopy. DNA studies have been carried out for metal complexes by electronic absorption spectroscopy. It is determined that metal complexes bind to DNA through intercalation. The complexes of Cu(II), Zn(II) and Pd(II) demonstrate significant activity against HeLa cells (cervical cancer).

Kevill,Foss

, p. 2837 (1967)

Shain,Kirsch

, p. 5848 (1968)

Methylation with Dimethyl Carbonate/Dimethyl Sulfide Mixtures: An Integrated Process without Addition of Acid/Base and Formation of Residual Salts

Chan, Bun,Lui, Matthew Y.,Lui, Yuen Wai

, (2022/01/08)

Dimethyl sulfide, a major byproduct of the Kraft pulping process, was used as an inexpensive and sustainable catalyst/co-reagent (methyl donor) for various methylations with dimethyl carbonate (as both reagent and solvent), which afforded excellent yields of O-methylated phenols and benzoic acids, and mono-C-methylated arylacetonitriles. Furthermore, these products could be isolated using a remarkably straightforward workup and purification procedure, realized by dimethyl sulfide‘s neutral and distillable nature and the absence of residual salts. The likely mechanisms of these methylations were elucidated using experimental and theoretical methods, which revealed that the key step involves the generation of a highly reactive trimethylsulfonium methylcarbonate intermediate. The phenol methylation process represents a rare example of a Williamson-type reaction that occurs without the addition of a Br?nsted base.

Cobalt single atoms anchored on nitrogen-doped porous carbon as an efficient catalyst for oxidation of silanes

Yang, Fan,Liu, Zhihui,Liu, Xiaodong,Feng, Andong,Zhang, Bing,Yang, Wang,Li, Yongfeng

supporting information, p. 1026 - 1035 (2021/02/09)

The oxidation reactions of organic compounds are important transformations for the fine and bulk chemical industry. However, they usually involve the use of noble metal catalysts and suffer from toxic or environmental issues. Here, an efficient, environmentally friendly, and atomically dispersed Co catalyst (Co-N-C) was preparedviaa simple, porous MgO template and etching method using 1,10-phenanthroline as C and N sources, and CoCl2·6H2O as the metal source. The obtained Co-N-C catalyst exhibits excellent catalytic performance for the oxidation of silanes with 97% isolated yield of organosilanol under mild conditions (room temperature, H2O as an oxidant, 1.8 h), and good stability with 95% isolated yield after nine consecutive reactions. The turnover frequency (TOF) is as high as 381 h?1, exceeding those of most non-noble metal catalysts and some noble metal catalysts. Aberration-corrected high-angle annular dark-field scanning transmission electron microscopy (HAADF-STEM), extended X-ray absorption fine structure (EXAFS), and wavelet transform (WT) spectroscopy corroborate the existence of atomically dispersed Co. The coordination numbers of Co affected by the pyrolysis temperature in Co-N-C-700, Co-N-C-800, and Co-N-C-900 are 4.1, 3.6, and 2.2, respectively. Owing to a higher Co-N3content, Co-N-C-800 shows more outstanding catalytic performance than Co-N-C-700 and Co-N-C-800. Moreover, density functional theory (DFT) calculations reveal that the Co-N3structure exhibits more activity compared with Co-N4and Co-N2, which is because the Co atom in Co-N3was bound with both H atom and Si atom, and it induced the longest Si-H bond.

Ni-NiO heterojunctions: a versatile nanocatalyst for regioselective halogenation and oxidative esterification of aromatics

Bhardwaj, Nivedita,Goel, Bharat,Indra, Arindam,Jain, Shreyans K.,Singh, Ajit Kumar,Tripathi, Nancy

, p. 14177 - 14183 (2021/08/16)

Herein, we report a facile method for the synthesis of Ni-NiO heterojunction nanoparticles, which we utilized for the nuclear halogenation reaction of phenol and substituted phenols usingN-bromosuccinimide (NBS). A remarkablepara-selectivity was achieved for the halogenated products under semi-aqueous conditions. Interestingly, blocking of thepara-position of phenol offeredortho-selective halogenation. In addition, the Ni-NiO nanoparticles catalyzed the oxidative esterification of carbonyl compounds with alcohol, diol or dithiol in the presence of a catalytic amount of NBS. It was observed that the aromatic carbonyls substituted with an electron-donating group favoured nuclear halogenation, whereas an electron-withdrawing group substitution in carbonyl compounds facilitated the oxidation reaction. In addition, the catalyst was magnetically separated and recycled 10 times. The tuned electronic structure at the Ni-NiO heterojunction controlled selectivity and activity as no suchpara-selectivity was observed with commercially available NiO or Ni nanoparticles.

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