(S)-Ethyl 4-bromo-3-hydroxybutanoate

Base Information

• Chemical Name: (S)-Ethyl 4-bromo-3-hydroxybutanoate
• CAS No.: 95537-36-3
• Molecular Formula: C₆H₁₁BrO₃
• Molecular Weight: 211.056
• European Community (EC) Number: 619-147-2
• DSSTox Substance ID: DTXSID90369976
• Nikkaji Number: J1.624.491K
• Wikidata: Q82157274
• Mol file: 95537-36-3.mol

Synonyms:95537-36-3;(S)-Ethyl 4-bromo-3-hydroxybutanoate;ethyl (3S)-4-bromo-3-hydroxybutanoate;ethyl (S)-4-bromo-3-hydroxybutyrate;(S)-4-BROMO-3-HYDROXYBUTYRIC ACID ETHYL ETHER;Ethyl (S)-(-)-4-bromo-3-hydroxybutyrate;Ethyl-(S)-(-)-4-Bromo-3-hydroxybutanoate;ETHYL (S)-4-BROMO-3-HYDROXYBUTANOATE;SCHEMBL1405832;DTXSID90369976;AIZRKZQHJNWBEI-YFKPBYRVSA-N;(S)-Ethyl4-bromo-3-hydroxybutanoate;AKOS016842845;ethyl (3s)-4-bromo-3-hydroxybutyrate;AC-13919;CS-0370350;ETHYL(S)-4-BROMO-3-HYDROXYBUTANOATE;(S)-3-Hydroxy-4-bromobutyric acid ethyl ester;Butanoic acid,4-bromo-3-hydroxy-,ethyl ester,(3R)-;Butanoic acid,4-bromo-3-hydroxy-,ethyl ester,(3S)-;Ethyl (S)-(-)-4-bromo-3-hydroxybutyrate, technical grade

Chemical Property of (S)-Ethyl 4-bromo-3-hydroxybutanoate

Chemical Property:

• Appearance/Colour: clear yellow liquid
• Vapor Pressure: 0.000329mmHg at 25°C
• Refractive Index: n20/D 1.474(lit.)
• Boiling Point: 285.1 °C at 760 mmHg
• PKA: 13.03±0.20(Predicted)
• Flash Point: 126.2 °C
• PSA: 46.53000
• Density: 1.485 g/cm³
• LogP: 0.69540
• Storage Temp.: 2-8°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 209.98916
• Heavy Atom Count: 10
• Complexity: 105

Purity/Quality:

99%, ^*data from raw suppliers

(S)-Ethyl 4-bromo-3-hydroxybutanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)CC(CBr)O
• Isomeric SMILES: CCOC(=O)C[C@@H](CBr)O

Technology Process of (S)-Ethyl 4-bromo-3-hydroxybutanoate

There total 13 articles about (S)-Ethyl 4-bromo-3-hydroxybutanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

ethanol (64-17-5) + (S)-4-bromomethyl-β-lactone (1133438-98-8) → (S)-4-bromo-3-hydroxy-butyric acid ethyl ester (32224-01-4,95310-94-4,128052-98-2,95537-36-3)

Guidance literature:

With toluene-4-sulfonic acid; at 60 ℃; for 1h;

DOI:10.1002/adsc.201200901

Reference yield: 95.0%

4-bromoethyl acetoacetate (13176-46-0) → (S)-4-bromo-3-hydroxy-butyric acid ethyl ester (32224-01-4,95310-94-4,128052-98-2,95537-36-3)

Guidance literature:

With D-glucose; broth E_. coli HB₁₀₁; pNTS₁G; NADP; In various solvent(s); at 30 ℃; for 20h; pH=6.5; Enzymatic reaction;

DOI:10.1016/S0957-4166(01)00279-8

Reference yield: 90.0%

ethanol (64-17-5) + (3S)-hydroxy-γ-butyrolactone (5469-16-9,58081-05-3,131432-37-6,7331-52-4) → (S)-4-bromo-3-hydroxy-butyric acid ethyl ester (32224-01-4,95310-94-4,128052-98-2,95537-36-3)

Guidance literature:

With hydrogen bromide; acetic acid; at 60 ℃; for 6h;

DOI:10.1016/S0957-4166(99)00169-X

upstream raw materials:

4-bromoethyl acetoacetate

ethanol

(3S)-hydroxy-γ-butyrolactone

ethyl acetoacetate

Downstream raw materials:

(R)-4-cyano-3-hydroxybutyric acid,ethyl ester

(R)-ethyl 4-cyano-3-hydroxybutyrate

L-carnitine

(S)-carnitin

Refernces

• 1、 Chen, Xiang,Liu, Zhi-Qiang,Huang, Jian-Feng,Lin, Chao-Ping,Zheng, Yu-Guo. "Asymmetric synthesis of optically active methyl-2-benzamido-methyl-3-hydroxy-butyrate by robust short-chain alcohol dehydrogenases from Burkholderia gladioli". . p. 12328 - 12331. Retrieved 2015/07/27.
• 2、 Xu, Guochao,Yu, Huilei,Xu, Jianhe. "Facile access to chiral alcohols with pharmaceutical relevance using a ketoreductase newly mined from Pichia guilliermondii". . p. 349 - 354. Retrieved 2013/08/22.