(R)-Methyl 4-chloro-3-hydroxybutanoate

Base Information

• Chemical Name: (R)-Methyl 4-chloro-3-hydroxybutanoate
• CAS No.: 88496-70-2
• Molecular Formula: C5H9ClO3
• Molecular Weight: 152.578
• Hs Code.: 2918199090
• European Community (EC) Number: 677-464-1
• DSSTox Substance ID: DTXSID80448305
• Nikkaji Number: J1.038.402H
• Wikidata: Q72451806
• Mol file: 88496-70-2.mol

Synonyms:88496-70-2;(R)-Methyl 4-chloro-3-hydroxybutanoate;Methyl (R)-4-Chloro-3-hydroxybutyrate;(R)-4-Chloro-3-hydroxybutyric acid methyl ester;methyl (3R)-4-chloro-3-hydroxybutanoate;(R)-Methyl-4-cloro-3-hydroxybutyrate;Butanoic acid, 4-chloro-3-hydroxy-, methyl ester, (3R)-;(R)4-Chloro-3-hydroxybutyric Acid methyl ester;SCHEMBL1405995;DTXSID80448305;WMRINGSAVOPXTE-SCSAIBSYSA-N;MFCD00273367;AKOS015848750;Methyl-4-chloro-3(R)-hydroxybutyrate;(R)-Methyl4-chloro-3-hydroxybutanoate;(R)methyl 4-chloro-3-hydroxybutanoate;methyl 3R-4-chloro-3-hydroxybutanoate;(R)-Methyl-4-chloro-3-hydroxybutyrate;methyl (3R)-4-chloro-3-hydroxybutyrate;AC-24011;DS-16798;Methyl (R)-4-Chloro-3-Hydroxy Butyrate;CS-0259583;M1483;EN300-73662;(3R)-4-Chloro-3-hydroxybutyric acid methylester

Chemical Property of (R)-Methyl 4-chloro-3-hydroxybutanoate

Chemical Property:

• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: 1.451
• Boiling Point: 248.644 °C at 760 mmHg
• PKA: 12.73±0.20(Predicted)
• Flash Point: 104.176 °C
• PSA: 46.53000
• Density: 1.232 g/cm³
• LogP: 0.14920
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• 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% ^*data from raw suppliers

(R)-4-Chloro-3-hydroxybutyricAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC(CCl)O
• Isomeric SMILES: COC(=O)C[C@H](CCl)O

Technology Process of (R)-Methyl 4-chloro-3-hydroxybutanoate

There total 7 articles about (R)-Methyl 4-chloro-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: 48.0%

methyl 4-chloro-3-hydroxybutanoate (10488-68-3) → (R)-3-hydroxybutyrolactone (58081-05-3) + methyl (R)-4-chloro-3-hydroxybutyrate (88496-70-2) + (3S)-hydroxy-γ-butyrolactone (5469-16-9,58081-05-3,131432-37-6,7331-52-4)

Guidance literature:

With sodium hydroxide; Enterobacter sp.DS-S-75; at 30 ℃; for 40h; pH=6.7; Further Variations:; Reagents; Product distribution; Enzymatic reaction;

DOI:10.1002/adsc.200390050

Reference yield: 40.0%

methyl 4-chloro-3-hydroxybutanoate (10488-68-3) + sodium cyanide (143-33-9,25596-52-5) → methyl (R)-4-chloro-3-hydroxybutyrate (88496-70-2) + methyl (S)-4-chloro-3-hydroxybutanoate (86728-93-0) + (S)-3-hydroxy-4-cyanobutyric acid methylester (150966-86-2)

Guidance literature:

With halohydrin dehalogenase Trp₂₄₉Phe mutant; Tris-SO₄ buffer; at 22 ℃; for 5h; pH=7.5;

DOI:10.1021/ol061369h

Reference yield: 20.0%

Methyl 4-chloroacetoacetate (32807-28-6,935731-94-5) → methyl (R)-4-chloro-3-hydroxybutyrate (88496-70-2) + methyl (S)-4-chloro-3-hydroxybutanoate (86728-93-0)

Guidance literature:

at 30 ℃; for 24h; Yields of byproduct given; Kroekera sp. No_. 2201 (AKU 4705) growning in methanol;

DOI:10.1016/S0040-4039(00)84610-9

upstream raw materials:

Methyl 4-chloroacetoacetate

methyl 4-chloro-3-hydroxybutanoate

Methyl (+/-)-3,4-epoxybutanoate

sodium cyanide

Downstream raw materials:

L-carnitine

(R)-4-chloro-3-hydroxy-1-p-toluenesulfonyloxybutane

Refernces

• 1、 Barros-Filho, Bartholomeu A.,Nunes, Fatima M.,de Oliveira, Maria da Conceicao F.,Lemos, Telma L.G.,de Mattos, Marcos C.,de Gonzalo, Gonzalo,Gotor-Fernandez, Vicente,Gotor, Vicente. "Bioreduction of prochiral ketones by growing cells of Lasiodiplodia theobromae: Discovery of a versatile biocatalyst for asymmetric synthesis". experimental part. p. 37 - 40. Retrieved 2010/12/18.
• 2、 Bisogno, Fabricio R.,Lavandera, Ivan,Kroutil, Wolfgang,Gotor, Vicente. "Tandem concurrent processes: One-pot single-catalyst biohydrogen transfer for the simultaneous preparation of enantiopure secondary alcohols". supporting information; scheme or table. p. 1730 - 1732. Retrieved 2009/07/11.