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Ethyl S-4-chloro-3-hydroxybutyrate

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Ethyl S-4-chloro-3-hydroxybutyrate Basic information

Product Name:
Ethyl S-4-chloro-3-hydroxybutyrate
Synonyms:
  • ethyl()-4-chloro-3-hydroxybutanoate
  • Ethyl(S)-4-chloro-3-hydroxybutylate
  • S-4-Chloro-3-hydroxybutyrate
  • ETHYL (S)-(-)-4-CHLORO-3-HYDROXYBUTANOATE
  • ETHYL (S)-4-CHLORO-3-HYDROXYBUTANOATE
  • (-)-ETHYL (S)-4-CHLORO-3-HYDROXYBUTYRATE
  • ETHYL (S)-(-)-4-CHLORO-3-HYDROXYBUTYRATE
  • ETHYL (S)-4-CHLORO-3-HYDROXYBUTYRATE
CAS:
86728-85-0
MF:
C6H11ClO3
MW:
166.6
EINECS:
617-912-5
Product Categories:
  • chiral
  • Alcohols, Hydroxy Esters and Derivatives
  • Chiral Compounds
  • Starting Raw Materials & Intermediates
  • Chiral Building Blocks
  • Simple Alcohols (Chiral)
  • Synthetic Organic Chemistry
  • Chiral Compound
  • Chiral Building Blocks
  • Esters
  • Organic Building Blocks
  • 86728-85-0
Mol File:
86728-85-0.mol
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Ethyl S-4-chloro-3-hydroxybutyrate Chemical Properties

alpha 
-14.5 º (c=neat)
Boiling point:
93-95 °C5 mm Hg(lit.)
Density 
1.19 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.453(lit.)
Flash point:
109 °C
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
form 
Liquid
pka
13.23±0.20(Predicted)
color 
Clear colorless to yellow
optical activity
[α]23/D 14°, neat
BRN 
4657170
InChI
InChI=1S/C6H11ClO3/c1-2-10-6(9)3-5(8)4-7/h5,8H,2-4H2,1H3/t5-/m0/s1
InChIKey
ZAJNMXDBJKCCAT-YFKPBYRVSA-N
SMILES
C(OCC)(=O)C[C@H](O)CCl
CAS DataBase Reference
86728-85-0(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi,Xn
Risk Statements 
41-22
Safety Statements 
26-36-39
RIDADR 
2810
WGK Germany 
3
HazardClass 
6.1
PackingGroup 
III
HS Code 
29181990

MSDS

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Ethyl S-4-chloro-3-hydroxybutyrate Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Uses

Atorvastatin Intermediate

Uses

Ethyl (S)-(?)-4-chloro-3-hydroxybutyrate can be used as a starting material in the synthesis of 4-amino-3-hydroxybutyric acid, a compound of pharmacological importance.

Biosynthesis

Bioreductions catalyzed by alcohol dehydrogenases (ADHs) play an essential role in synthesizing chiral alcohols. A novel ADH, SmADH31, obtained from the Stenotrophomonas maltophilia genome, which can tolerate extremely high concentrations (6 M) of both substrate and product. The coexpression of SmADH31 and glucose dehydrogenase from Bacillus subtilis in Escherichia coli meant that as much as 660 g L–1 (4.0 M) ethyl 4-chloroacetoacetate was completely converted into ethyl (S)-4-chloro-3-hydroxybutyrate [(S)-CHBE] in a monophasic aqueous system with a >99.9% ee value and a high space-time yield (2664 g L–1 d–1). In the 100 ml-scale monophasic aqueous system (in triplicate), 66.0 g COBE (single batch charge) can be completely converted to (S)-CHBE (ee >99.9%) in only 6 h with 2 g of the SmADH31/GDH co-expressing cells. After extraction and evaporation, 61.6 g (S)-CHBE was isolated with 92% yield[1].

General Description

Ethyl (S)-4-chloro-3-hydroxybutanoate is a chiral intermediate generally used to prepare atorvastatin, a cholesterol-lowering drug.

References

[1] Zeyu Yang. “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.” Organic Process Research & Development 24 6 (2020): 1068–1076.

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