(S)-methyl-4-chloro-3-hydroxybutyrate

Base Information

• Chemical Name: (S)-methyl-4-chloro-3-hydroxybutyrate
• CAS No.: 86728-93-0
• Molecular Formula: C5H9ClO3
• Molecular Weight: 152.578
• Hs Code.: 2918199890
• DSSTox Substance ID: DTXSID60363764
• Nikkaji Number: J456.523A
• Wikidata: Q72489550
• Mol file: 86728-93-0.mol

Synonyms:86728-93-0;(S)-methyl-4-chloro-3-hydroxybutyrate;(S)-Methyl 4-cloro-3-hydroxybutyrate;Methyl (S)-4-chloro-3-hydroxybutyrate;methyl (3S)-4-chloro-3-hydroxybutanoate;(S)-methyl 4-chloro-3-hydroxybutanoate;(S)-METHYL-4-CLORO-3-HYDROXYBUTYRATE;methyl (s)-4-chloro-3-hydroxybutanoate;SCHEMBL1405741;DTXSID60363764;AKOS006277976;(S)-methyl 4-chloro-3-hydroxybutyrate;(S)-methyl4-chloro-3-hydroxybutanoate;BS-24144;CS-0456671;A19567;(S)-3-Hydroxy-4-chlorobutyric acid methyl ester;(s)-4-chloro-3-hydroxybutanoic acid methyl ester

Chemical Property of (S)-methyl-4-chloro-3-hydroxybutyrate

Chemical Property:

• Vapor Pressure: 0.00387mmHg at 25°C
• Refractive Index: 1.45
• Boiling Point: 248.6 °C at 760 mmHg
• PKA: 12.73±0.20(Predicted)
• Flash Point: 104.2 °C
• PSA: 46.53000
• Density: 1.232 g/cm³
• LogP: 0.14920
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 152.0240218
• Heavy Atom Count: 9
• Complexity: 94.2

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-Methyl-4-chloro-3-hydroxybutyrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC(CCl)O
• Isomeric SMILES: COC(=O)C[C@@H](CCl)O
• Uses: (S)-Methyl-4-chloro-3-hydroxybutyrate

Technology Process of (S)-methyl-4-chloro-3-hydroxybutyrate

There total 18 articles about (S)-methyl-4-chloro-3-hydroxybutyrate 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: 96.0%

methanol (67-56-1) + (S)-epichlorohydrin (67843-74-7,24969-06-0,13403-37-7) + carbon monoxide (201230-82-2) → methyl (S)-4-chloro-3-hydroxybutanoate (86728-93-0)

Guidance literature:

With 3-HYDROXYPYRIDINE; dicobalt octacarbonyl; In tetrahydrofuran; at 55 ℃; for 9h; under 31028.9 Torr;

DOI:10.1021/jo982336l

Reference yield: 95.0%

→ methyl (S)-4-chloro-3-hydroxybutanoate (86728-93-0)

Guidance literature:

Reference yield: 91.0%

Methyl 4-chloroacetoacetate (32807-28-6,935731-94-5) → methyl (S)-4-chloro-3-hydroxybutanoate (86728-93-0)

Guidance literature:

With NAD; isopropyl alcohol; In aq. phosphate buffer; at 30 ℃; for 4h; pH=7; Reagent/catalyst; stereoselective reaction; Microbiological reaction; Green chemistry; Enzymatic reaction;

DOI:10.1039/c9cy01794a

upstream raw materials:

[9,9']Biphenanthrenyl-10,10'-diol; compound with 4-chloro-3-hydroxy-butyric acid methyl ester

[9,9']Biphenanthrenyl-10,10'-diol; compound with 4-chloro-3-hydroxy-butyric acid methyl ester

Methyl 4-chloroacetoacetate

methanol

Downstream raw materials:

(S)-4-amino-3-hydroxybutyric acid methyl ester

methyl (3S)-4-azido-3-hydroxybutanoate

(3S)-4-chloro-1,3-butanediol

methyl (S)-4-chloro-3-tert-butoxybutyrate

Refernces

• 1、 Chen, Rong,Liu, Qinghai,Wang, Hualei,Wei, Dongzhi,Xie, Youyu,Yang, Zeyu,Ye, Wenjie. "Efficient Asymmetric Synthesis of Ethyl (S)-4-Chloro-3-hydroxybutyrate Using Alcohol Dehydrogenase SmADH31 with High Tolerance of Substrate and Product in a Monophasic Aqueous System". . p. 1068 - 1076. Retrieved 2020/07/06.
• 2、 Sun, Qi,Meng, Xiangju,Xiao, Feng-Shou,Liu, Xiao,Zhang, Xiaoming,Yang, Yan,Yang, Qihua. "Mesoporous cross-linked polymer copolymerized with chiral BINAP ligand coordinated to a ruthenium species as an efficient heterogeneous catalyst for asymmetric hydrogenation". supporting information. p. 10505 - 10507,3. Retrieved 2020/09/02.