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1852-04-6

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1852-04-6 Usage

Description

Undecanedioic acid, also known as 'long-chain dicarboxylic acids', is a dibasic acid in the form of a white powder or flake. It is an alpha, omega-dicarboxylic acid that is nonane with two carboxylic acid groups at positions C-1 and C-9. Undecanedioic acid has a role as a metabolite and is a conjugate acid of an undecanedioic acid anion. It is a bioactive compound found in Polygala tenuifolia root, which is used as a functional food due to its attractive health benefits.

Uses

Used in Functional Foods:
Undecanedioic acid is used as a bioactive compound in functional foods for its attractive health benefits.
Used in Corrosion Inhibitors:
Undecanedioic acid is used as a corrosion inhibitor to protect materials from the damaging effects of corrosion.
Used in Hot Melt Adhesives:
Undecanedioic acid is used as a component in hot melt adhesives, providing strong bonding properties.
Used in High-Performance Polyamides/Nylon:
Undecanedioic acid is used in the production of high-performance polyamides and nylon, enhancing their durability and strength.
Used in Metal-Working Fluids:
Undecanedioic acid is used in metal-working fluids to improve the efficiency and performance of the manufacturing process.
Used in Lubricants:
Undecanedioic acid is used as a lubricant to reduce friction and wear in various mechanical applications.
Used in Adhesives:
Undecanedioic acid is used in the formulation of adhesives, providing strong bonding capabilities.
Used in Powder Coatings:
Undecanedioic acid is used in powder coatings to provide a durable and protective finish for various surfaces.
Used in Medical Research:
Undecanedioic acid has been found in parts of human aortas with advanced atherosclerotic lesions, associated with intercellular matrix macromolecules and specifically with elastin. It may be the result of an increased hydrolysis of esters and/or a decreased esterification. Additionally, it has been found in the urine from patients under hopantenate therapy during episodes of Reye's-like syndrome, indicating its potential role in medical research and understanding of certain diseases.

Flammability and Explosibility

Nonflammable

Synthesis

Undecanedioic acid is obtained by reacting α -nitro ketone and NaOH in MeOH.To a solution of α -nitro ketone (0.7 mmol) in MeOH (4.2 ml), 25 ml of 0.5 M Na2HPO4 in a 1 N of NaOH were added and the resulting mixture was heated at 70 °C for 1-4 h, then Oxone (1.75 mmol) in water (3 ml) was added to the cold solution (r. t.). After 4 h the mixture was diluted with brine (10 ml), acidified to pH=2 with a 10% solution of HCl and extracted with EtOAc (3 x 20 ml). The combined organic layers were washed with brine (10 ml), dried over Na2SO4 and evaporated to yield pure dicarboxylic acid.Fig The synthetic method 2 of Undecanedioic acid.

Check Digit Verification of cas no

The CAS Registry Mumber 1852-04-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,5 and 2 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1852-04:
(6*1)+(5*8)+(4*5)+(3*2)+(2*0)+(1*4)=76
76 % 10 = 6
So 1852-04-6 is a valid CAS Registry Number.
InChI:InChI=1/C40H38N4O16/c45-33(46)5-1-17-21(9-37(53)54)29-14-27-19(3-7-35(49)50)23(11-39(57)58)31(43-27)16-32-24(12-40(59)60)20(4-8-36(51)52)28(44-32)15-30-22(10-38(55)56)18(2-6-34(47)48)26(42-30)13-25(17)41-29/h13-16,41,44H,1-12H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-

1852-04-6 Well-known Company Product Price

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  • Aldrich

  • (177962)  Undecanedioicacid  97%

  • 1852-04-6

  • 177962-1G

  • 774.54CNY

  • Detail

1852-04-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Undecanedioic acid

1.2 Other means of identification

Product number -
Other names Undecanedioate

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:1852-04-6 SDS

1852-04-6Synthetic route

11-hydroxyundecanoic acid
3669-80-5

11-hydroxyundecanoic acid

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With chromium(VI) oxide; periodic acid In water; acetonitrile at 0 - 5℃; for 1.25h;90%
With sodium bromate; hydrogen bromide; tert-butyl alcohol In tetrachloromethane; water for 2h; Ambient temperature;75%
Oxydation;
Methyl 11-nitroundecanoate
128224-90-8

Methyl 11-nitroundecanoate

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With hydrogenchloride In water for 4h; Nef reaction; Reflux;79%
carbon monoxide
201230-82-2

carbon monoxide

non-2-en-1-ol
22104-79-6

non-2-en-1-ol

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With HeMaRaphos; water; toluene-4-sulfonic acid; palladium dichloride In tetrahydrofuran at 125℃; under 30003 Torr; for 24h; Autoclave; Green chemistry; regioselective reaction;63%
dimethyl undecanedioate
4567-98-0

dimethyl undecanedioate

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With porcine liver esterase; sodium hydroxide; phosphate buffer for 6h;49%
Ricinoleic acid
141-22-0

Ricinoleic acid

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With recombinant escherichia coli BL21(DE3); Tween 84 In aq. buffer at 35℃; for 2h; pH=8; Enzymatic reaction;36%
cycloundecanone
878-13-7

cycloundecanone

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With chromium(VI) oxide; acetic acid
docos-11-enoic acid methyl ester
2463-07-2

docos-11-enoic acid methyl ester

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With potassium permanganate; acetone
With ozone
12-Hydroxystearic acid
106-14-9

12-Hydroxystearic acid

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With alkaline KMNO4
With recombinant escherichia coli BL21(DE3); Tween 82 In aq. buffer at 35℃; for 2h; pH=8; Enzymatic reaction;
12-Hydroxystearic acid
106-14-9

12-Hydroxystearic acid

A

undecanedioic acid
1852-04-6

undecanedioic acid

B

1,12-dodecanedioic acid
693-23-2

1,12-dodecanedioic acid

Conditions
ConditionsYield
With nitric acid
With ammonium vanadate; nitric acid
With nitric acid
methyl 12-hydroxyoctadecanoate
6114-39-2, 7309-59-3, 82008-61-5, 141-23-1

methyl 12-hydroxyoctadecanoate

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With ammonium vanadate; nitric acid; copper
11-oxoundecanoic acid
53163-99-8

11-oxoundecanoic acid

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With alkaline KMNO4
undecanedioic acid monomethyl ester
3927-60-4

undecanedioic acid monomethyl ester

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With sodium hydroxide
4-oxo-1,9-nonanedicarboxylic acid
87358-48-3

4-oxo-1,9-nonanedicarboxylic acid

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With potassium hydroxide; hydrazine hydrate; diethylene glycol
12-oxooctadecanoic acid
925-44-0

12-oxooctadecanoic acid

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With alkaline KMNO4
methyl 12-oxooctadecanoate
2380-27-0

methyl 12-oxooctadecanoate

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With ammonium vanadate; nitric acid; copper
triundecanoin
13552-80-2

triundecanoin

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
beim Abbau im menschlichen Organismus;
1,11-undecanedinitrile
71172-36-6

1,11-undecanedinitrile

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With potassium hydroxide durch Verseifen;
(alkaline hydrolysis);
undec-5-ynedioic acid
65111-12-8

undec-5-ynedioic acid

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With hydrogen; nickel
With hydrogen; platinum
methyl 4-(2-oxo-1-cycloheptyl)butyrate
82614-33-3

methyl 4-(2-oxo-1-cycloheptyl)butyrate

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
Multistep reaction;
(11Z,14R)-14-hydroxyicos-11-enoic acid

(11Z,14R)-14-hydroxyicos-11-enoic acid

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With potassium permanganate; sodium periodate
Undeca-2,9-diynedioic acid

Undeca-2,9-diynedioic acid

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With hydrogen; nickel In ethanol
10-undecenoic acid
112-38-9

10-undecenoic acid

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With chromium(VI) oxide; sodium tetrahydroborate; sulfuric acid; water; tert-butyl alcohol 1.) THF, a.) r.t., 2 h, b.) 50-55 deg C, 4 h, 2.) acetone, r.t., 10 h; Yield given. Multistep reaction;
Multi-step reaction with 6 steps
1: methanol / 6 h / 0 - 20 °C
2: ozone; triphenylphosphine / methanol; dichloromethane / 6 h / -78 - 20 °C
3: sodium hydroxide / 1.5 h / 0 - 20 °C
4: methanesulfonyl chloride; triethylamine / dichloromethane / 0.17 h / 20 °C
5: palladium 10% on activated carbon; hydrogen / ethyl acetate / 2 h / 20 °C / 2250.23 Torr
6: hydrogenchloride / water / 4 h / Reflux
View Scheme
cyclododecanol
1724-39-6

cyclododecanol

A

azelaic acid
123-99-9

azelaic acid

B

heptanedioic acid
111-16-0

heptanedioic acid

C

octane-1,8-dioic acid
505-48-6

octane-1,8-dioic acid

D

1,10-decanedioic acid
111-20-6

1,10-decanedioic acid

E

undecanedioic acid
1852-04-6

undecanedioic acid

F

1,12-dodecanedioic acid
693-23-2

1,12-dodecanedioic acid

Conditions
ConditionsYield
With nitric acid In Cyclopentane for 0.166667h; Product distribution; other temperature, other concentration of HNO3;;A n/a
B n/a
C n/a
D 0.020 (unit not given)
E 0.110 (unit not given)
F 0.824 (unit not given)
cyclododecanol
1724-39-6

cyclododecanol

A

1,10-decanedioic acid
111-20-6

1,10-decanedioic acid

B

undecanedioic acid
1852-04-6

undecanedioic acid

C

1,12-dodecanedioic acid
693-23-2

1,12-dodecanedioic acid

Conditions
ConditionsYield
With nitric acid at 50℃; for 0.166667h; Further byproducts given. Title compound not separated from byproducts;A 0.021 (unit not given)
B 0.110 (unit not given)
C 0.824
cyclododecanone
830-13-7

cyclododecanone

A

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

B

Adipic acid
124-04-9

Adipic acid

C

1,10-decanedioic acid
111-20-6

1,10-decanedioic acid

D

succinic acid
110-15-6

succinic acid

E

undecanedioic acid
1852-04-6

undecanedioic acid

F

1,12-dodecanedioic acid
693-23-2

1,12-dodecanedioic acid

Conditions
ConditionsYield
With nitric acid for 0.75h; Product distribution; other temperature, other concentration of HNO3;;A n/a
B n/a
C 0.030 (unit not given)
D n/a
E 0.117 (unit not given)
F 0.742 (unit not given)
cyclododecanone
830-13-7

cyclododecanone

A

1,10-decanedioic acid
111-20-6

1,10-decanedioic acid

B

undecanedioic acid
1852-04-6

undecanedioic acid

C

1,12-dodecanedioic acid
693-23-2

1,12-dodecanedioic acid

Conditions
ConditionsYield
With nitric acid at 45℃; for 0.166667h; Further byproducts given. Title compound not separated from byproducts;A 0.030 (unit not given)
B 0.117 (unit not given)
C 0.742
11,13-Dihydroxy-tetracosanoic acid methyl ester

11,13-Dihydroxy-tetracosanoic acid methyl ester

A

lauric acid
143-07-7

lauric acid

B

1,10-decanedioic acid
111-20-6

1,10-decanedioic acid

C

undecylenic acid
112-37-8

undecylenic acid

D

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With potassium permanganate In acetic acid Product distribution;
2,3,14-Trioxabicyclo<9.2.1>tetradecane

2,3,14-Trioxabicyclo<9.2.1>tetradecane

A

11-oxoundecanoic acid
53163-99-8

11-oxoundecanoic acid

B

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
In benzene-d6 at 80℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
2-nitrocycloundecanone
141882-58-8

2-nitrocycloundecanone

undecanedioic acid
1852-04-6

undecanedioic acid

Conditions
ConditionsYield
With Oxone; sodium hydroxide; disodium hydrogenphosphate; water 1.) MeOH, 70 deg C, 4 h, 2.) MeOH, r.t., 4 h; Yield given. Multistep reaction;
methanol
67-56-1

methanol

undecanedioic acid
1852-04-6

undecanedioic acid

dimethyl undecanedioate
4567-98-0

dimethyl undecanedioate

Conditions
ConditionsYield
With boron trifluoride at 65℃; for 0.333333h;100%
With thionyl chloride at 20℃; for 6h;
With thionyl chloride for 1.5h; Reflux;192.62 g
undecanedioic acid
1852-04-6

undecanedioic acid

pentafluorophenyl trifloroacetate
14533-84-7

pentafluorophenyl trifloroacetate

bis(perfluorophenyl) undecanedioate

bis(perfluorophenyl) undecanedioate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h;100%
undecanedioic acid
1852-04-6

undecanedioic acid

2,3-Epoxypropyl methacrylate
106-91-2

2,3-Epoxypropyl methacrylate

1,11-bis({2-hydroxy-3-[(2-methylprop-2-enoyl)oxy]propyl})undecanedioate

1,11-bis({2-hydroxy-3-[(2-methylprop-2-enoyl)oxy]propyl})undecanedioate

Conditions
ConditionsYield
With triphenylphosphine at 90℃; for 3h;99%
With methoxyhydroquinone; triphenylphosphine at 90℃; for 3h;99%
With triphenylphosphine at 90℃; for 3h; Concentration;99%
undecanedioic acid
1852-04-6

undecanedioic acid

11-chloro-11-oxoundecanoic acid

11-chloro-11-oxoundecanoic acid

Conditions
ConditionsYield
With oxalyl dichloride; N,N-dimethyl-formamide In tetrahydrofuran at 25℃; for 2h;99%
undecanedioic acid
1852-04-6

undecanedioic acid

undecanedioyl dichloride
45165-01-3

undecanedioyl dichloride

Conditions
ConditionsYield
With thionyl chloride at 20℃;95%
With thionyl chloride
With thionyl chloride
undecanedioic acid
1852-04-6

undecanedioic acid

1,11-undecanediamide
73154-82-2

1,11-undecanediamide

Conditions
ConditionsYield
With ammonia at 180 - 220℃; for 10h; Temperature;95%
Multi-step reaction with 2 steps
1: thionyl chloride / 1.5 h / Reflux
2: ammonia / methanol / 1 h / 40 °C
View Scheme
undecanedioic acid
1852-04-6

undecanedioic acid

(2S,4R)-1-[(2S)-2-azanyl-3,3-dimethylbutanoyl]-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]-4-oxidanylpyrrolidine-2-carboxamide
1448297-52-6

(2S,4R)-1-[(2S)-2-azanyl-3,3-dimethylbutanoyl]-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]-4-oxidanylpyrrolidine-2-carboxamide

10-[[(2S)-1-[(2S,4R)-4-hydroxy-2-([[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]carbamoyl)pyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]carbamoyl]decanoic acid

10-[[(2S)-1-[(2S,4R)-4-hydroxy-2-([[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]carbamoyl)pyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]carbamoyl]decanoic acid

Conditions
ConditionsYield
With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0℃; for 6h;78%
With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 0 - 20℃;76%
With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 12h; Inert atmosphere;67%
undecanedioic acid
1852-04-6

undecanedioic acid

(2S,4S)-1-[(2S)-2-amino-3,3-dimethylbutanoyl]-4-hydroxy-N-{[4-(4-methyl-1,3-thiazol-5-yl)-phenyl]methyl}pyrrolidine-2-carboxamide

(2S,4S)-1-[(2S)-2-amino-3,3-dimethylbutanoyl]-4-hydroxy-N-{[4-(4-methyl-1,3-thiazol-5-yl)-phenyl]methyl}pyrrolidine-2-carboxamide

11-(((S)-1-((2S,4S)-4hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)amino)-11-oxoundecanoic acid

11-(((S)-1-((2S,4S)-4hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)amino)-11-oxoundecanoic acid

Conditions
ConditionsYield
With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; Cooling with ice;76%
undecanedioic acid
1852-04-6

undecanedioic acid

C21H25N7O

C21H25N7O

C53H66N14O4*6ClH

C53H66N14O4*6ClH

Conditions
ConditionsYield
Stage #1: C21H25N7O With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.166667h; Cooling;
Stage #2: undecanedioic acid In N,N-dimethyl-formamide for 0.166667h; Further stages;
74%
undecanedioic acid
1852-04-6

undecanedioic acid

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Undecanedioic acid bis-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl) ester

Undecanedioic acid bis-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl) ester

Conditions
ConditionsYield
With Aliquat 336; potassium carbonate In dichloromethane; water Ambient temperature;72%
undecanedioic acid
1852-04-6

undecanedioic acid

<4.3.3>propellane-8,11-anti,anti-diol
82373-89-5

<4.3.3>propellane-8,11-anti,anti-diol

C23H36O4

C23H36O4

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 24h; Heating;70%
undecanedioic acid
1852-04-6

undecanedioic acid

template CS diol
110224-49-2

template CS diol

C62H64O4
110224-56-1

C62H64O4

Conditions
ConditionsYield
With dmap; 4-(dimethylamino)pyridine hydrochloride; dicyclohexyl-carbodiimide In chloroform for 14h; Heating;67%
undecanedioic acid
1852-04-6

undecanedioic acid

(rac)-4-(4-fluoro-2-methoxyphenyl)-N-{3-[(S-methylsulfonimidoyl)methyl]phenyl}-1,3,5-triazin-2-amine
1414943-88-6, 1414943-91-1, 1414943-94-4

(rac)-4-(4-fluoro-2-methoxyphenyl)-N-{3-[(S-methylsulfonimidoyl)methyl]phenyl}-1,3,5-triazin-2-amine

C29H36FN5O5S

C29H36FN5O5S

Conditions
ConditionsYield
With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In N,N-dimethyl-formamide at 40℃; for 3h;55%
undecanedioic acid
1852-04-6

undecanedioic acid

(x)C2H3F3O2*C31H38F3N7O2

(x)C2H3F3O2*C31H38F3N7O2

(x)C2H3F3O2*C42H56F3N7O5

(x)C2H3F3O2*C42H56F3N7O5

Conditions
ConditionsYield
With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 20℃; for 2h;52%
(6-(6-(4-methylpiperazin-1-yl)-1H-benzo[d]imidazol-2-yl)-1H-benzo[d]imidazol-2-yl)methylamine tetrahydrochloride

(6-(6-(4-methylpiperazin-1-yl)-1H-benzo[d]imidazol-2-yl)-1H-benzo[d]imidazol-2-yl)methylamine tetrahydrochloride

undecanedioic acid
1852-04-6

undecanedioic acid

C51H62N14O2*6ClH

C51H62N14O2*6ClH

Conditions
ConditionsYield
Stage #1: (6-(6-(4-methylpiperazin-1-yl)-1H-benzo[d]imidazol-2-yl)-1H-benzo[d]imidazol-2-yl)methylamine tetrahydrochloride; undecanedioic acid With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.166667h;
Stage #2: With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃;
Stage #3: With hydrogenchloride In methanol; water-d2
49.9%
undecanedioic acid
1852-04-6

undecanedioic acid

benzyl bromide
100-39-0

benzyl bromide

11-(benzyloxy)-11-oxoundecanoic acid

11-(benzyloxy)-11-oxoundecanoic acid

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;45%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;45%
undecanedioic acid
1852-04-6

undecanedioic acid

(2R,4S)-1-[(2S)-2-amino-3,3-dimethylbutanoyl]-4-hydroxy-N-[[4-(4-methylthiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide

(2R,4S)-1-[(2S)-2-amino-3,3-dimethylbutanoyl]-4-hydroxy-N-[[4-(4-methylthiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide

11-(((S)-1-((2R,4S)-4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)amino)-11-oxoundecanoic acid

11-(((S)-1-((2R,4S)-4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)amino)-11-oxoundecanoic acid

Conditions
ConditionsYield
With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 0 - 20℃; for 4h;43%
undecanedioic acid
1852-04-6

undecanedioic acid

8-O-(14-benzoylaconine) undecanedioate
1394033-52-3

8-O-(14-benzoylaconine) undecanedioate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 7h;34%
undecanedioic acid
1852-04-6

undecanedioic acid

(2S,4R)-1-[(2S)-2-amino-3,3-dimethylbutanoyl]-4-hydroxy-N-[(1S)-1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]ethyl]pyrrolidine-2-carboxamide hydrochloride

(2S,4R)-1-[(2S)-2-amino-3,3-dimethylbutanoyl]-4-hydroxy-N-[(1S)-1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]ethyl]pyrrolidine-2-carboxamide hydrochloride

11-(((S)-1-((2S,4R)-4-hydroxy-2-(((S)-1-(4-(4-methylthiazol-5-yl)phenyl)ethyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)amino)-11-oxoundecanoic acid

11-(((S)-1-((2S,4R)-4-hydroxy-2-(((S)-1-(4-(4-methylthiazol-5-yl)phenyl)ethyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)amino)-11-oxoundecanoic acid

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran; dichloromethane at 0℃; for 2h;31%
undecanedioic acid
1852-04-6

undecanedioic acid

1,3-bis(8-amino-3,6-di-tert-butyl-9H-carbazol-1-yl)urea

1,3-bis(8-amino-3,6-di-tert-butyl-9H-carbazol-1-yl)urea

C52H68N6O3

C52H68N6O3

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 24℃; for 40h; Inert atmosphere;29%
undecanedioic acid
1852-04-6

undecanedioic acid

(3E,5E,7E)-Deca-3,5,7-triene-1,10-diol
79563-45-4

(3E,5E,7E)-Deca-3,5,7-triene-1,10-diol

(4E,6E,8E)-1,12-Dioxa-cyclotricosa-4,6,8-triene-13,23-dione
79563-46-5

(4E,6E,8E)-1,12-Dioxa-cyclotricosa-4,6,8-triene-13,23-dione

Conditions
ConditionsYield
Heating;20%
undecanedioic acid
1852-04-6

undecanedioic acid

2',3'-O-isopropylideneuridine
362-43-6

2',3'-O-isopropylideneuridine

Undecanedioic acid bis-[(3aR,4R,6R,6aR)-6-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl] ester

Undecanedioic acid bis-[(3aR,4R,6R,6aR)-6-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl] ester

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dimethyl sulfoxide Ambient temperature;18%
undecanedioic acid
1852-04-6

undecanedioic acid

C48H40N6NiO4(2+)*2F6P(1-)

C48H40N6NiO4(2+)*2F6P(1-)

C70H72N6NiO8

C70H72N6NiO8

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In tetrahydrofuran at 20℃; for 91h;12%
undecanedioic acid
1852-04-6

undecanedioic acid

<4.3.3>propellane-8,11-anti,syn-diol
82373-88-4

<4.3.3>propellane-8,11-anti,syn-diol

C23H36O4

C23H36O4

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 48h; Heating;8%
undecanedioic acid
1852-04-6

undecanedioic acid

(2S,4R)-1-[(2S)-2-amino-3,3-dimethylbutanoyl]-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide hydrochloride
1448189-80-7

(2S,4R)-1-[(2S)-2-amino-3,3-dimethylbutanoyl]-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide hydrochloride

11-(((S)-1-((2S,4R)-4-hydroxy-2-(((S)-1-(4-(4-methylthiazol-5-yl)phenyl)ethyl)carbamoyl) pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)amino)-11-oxoundecanoic acid

11-(((S)-1-((2S,4R)-4-hydroxy-2-(((S)-1-(4-(4-methylthiazol-5-yl)phenyl)ethyl)carbamoyl) pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)amino)-11-oxoundecanoic acid

Conditions
ConditionsYield
Stage #1: undecanedioic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; for 0.5h; Inert atmosphere;
Stage #2: (2S,4R)-1-[(2S)-2-amino-3,3-dimethylbutanoyl]-4-hydroxy-N-{[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl}pyrrolidine-2-carboxamide hydrochloride In N,N-dimethyl-formamide at 25℃; for 1.5h; Inert atmosphere;
3.4%

1852-04-6Relevant articles and documents

Chemo-enzymatic synthesis of 11-hydroxyundecanoic acid and 1,11-undecanedioic acid from ricinoleic acid

Jang, Hyun-Young,Singha, Kaushik,Kim, Hwan-Hee,Kwon, Yong-Uk,Park, Jin-Byung

, p. 1089 - 1095 (2016)

A practical chemoenzymatic synthetic method for 11-hydroxyundecanoic acid and 1,11-undecanedioic acid from ricinoleic acid (12-hydroxyoleic acid) was investigated. Biotransformation of ricinoleic acid into the ester (3) via 12-ketooleic acid (2) was driven by recombinant Escherichia coli cells expressing an alcohol dehydrogenase from Micrococcus luteus and the Baeyer-Villiger monooxygenase from Pseudomonas putida KT2440. The carbon-carbon double bond of the ester (3) was chemically reduced, and the ester bond was hydrolyzed to afford n-heptanoic acid (5) and 11-hydroxyundecanoic acid (7), which were converted into other related derivatives. For example, 11-hydroxyundecanoic acid was transformed into 1,11-undecanedioic acid (8) under fairly mild reaction conditions. Whole-cell biotransformation at high cell density (i.e., 20 g dry cells per L) allowed the final ester product concentration and volumetric productivity to reach 53 mM and 6.6 mM h-1, respectively. The overall molar yield of 1,11-undecanedioic acid from ricinoleic acid was 55% based on the biotransformation and chemical transformation conversion yields of 84% and 65%, respectively.

Facile synthesis of gold icosahedra in an aqueous solution by reacting HAuCl4 with N-vinyl pyrrolidone

Yavuz, Mustafa S.,Li, Weiyang,Xia, Younan

, p. 13181 - 13187 (2009)

Herein we describe a protocol that generates Au icosahedra in high yields by simply mixing aqueous solutions of HAuCl4 and N-vinyl pyrrolidone. Our mechanistic study reveals that water plays an important role in this synthesis: as a nucleophile

Six New Polyacetylenic Alcohols from the Marine Sponges Petrosia sp. and Halichondria sp.

Gabriel, Adeyemi Francis,Li, Zhen,Kusuda, Ryouhei,Tanaka, Chiaki,Miyamoto, Tomofumi

, p. 469 - 475 (2015/09/07)

Six new polyacetylenic alcohols, termed strongylotriols A and B; pellynols J, K, and L; and isopellynol A, together with three known polyacetylenic alcohols, pellynols A, B, and C were isolated from the marine sponges Petrosia sp., and Halichondria sp. collected in Okinawa, Japan. Their planer structures were determined based on 2D-NMR and mass spectrometric analysis of the degraded products by RuCl3 oxidation. The absolute stereochemistry of isolates was examined by their Mosher's esters. The strongylotriols were found to be optically pure compounds, whereas the pellynols are diastereomeric mixtures at the C-6 position. Proliferation experiments using the HeLa and K562 cell lines suggested that the essential structural units for activity are the "hexa-2,4-diyn-1,6-diol" and "pent-1-en-4-yn-3-ol" on the termini.

Divergent process for C10, C11 and C12 ω-amino acid and α,ω-dicarboxylic acid monomers of polyamides from castor oil as a renewable resource

Koh, Moo-Hyun,Kim, Hyeonjeong,Shin, Nara,Kim, Hyun Su,Yoo, Dongwon,Kim, Young Gyu

, p. 1873 - 1878 (2012/08/07)

Polyamides have great potentials for diverse applications and the present production of their monomers mostly relies on resources from fossil fuel. Starting from undecylenic acid, a natural resource, we have developed both divergent and efficient processes for C10, C11 and C 12 ω-amino acid and α,ω-dicarboxylic acid monomers of the polyamides.

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