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Ethyl S-4-chloro-3-hydroxybutyrate

Product Name
Ethyl S-4-chloro-3-hydroxybutyrate
CAS No.
86728-85-0
Chemical Name
Ethyl S-4-chloro-3-hydroxybutyrate
Synonyms
ETHYL (S)-4-CHLORO-3-HYDROXYBUTANOATE;ETHYL (S)-4-CHLORO-3-HYDROXYBUTYRATE;ETHYL (S)-(-)-4-CHLORO-3-HYDROXYBUTYRATE;SECHB;AST-4;PEFC-026;(S)-(?)-4-chL;(S)-Ethyl 4-chloro-3-;oro-3-hydroxybutyrate;4-chloro-3-hydroxyhexanoate
CBNumber
CB9448087
Molecular Formula
C6H11ClO3
Formula Weight
166.6
MOL File
86728-85-0.mol
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Ethyl S-4-chloro-3-hydroxybutyrate Property

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

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H318Causes serious eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
460524
Product name
Ethyl (S)-(?)-4-chloro-3-hydroxybutyrate
Purity
96%
Packaging
1g
Price
$15.48
Updated
2024/03/01
Sigma-Aldrich
Product number
460524
Product name
Ethyl (S)-(?)-4-chloro-3-hydroxybutyrate
Purity
96%
Packaging
5g
Price
$29.12
Updated
2024/03/01
TCI Chemical
Product number
C1717
Product name
Ethyl (S)-4-Chloro-3-hydroxybutyrate
Purity
>95.0%(GC)
Packaging
5g
Price
$47
Updated
2024/03/01
TCI Chemical
Product number
C1717
Product name
Ethyl (S)-4-Chloro-3-hydroxybutyrate
Purity
>95.0%(GC)
Packaging
25g
Price
$85
Updated
2024/03/01
Alfa Aesar
Product number
L18554
Product name
Ethyl (S)-(-)-4-chloro-3-hydroxybutyrate, 98%, ee 98%
Packaging
1g
Price
$25.65
Updated
2024/03/01
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Ethyl S-4-chloro-3-hydroxybutyrate Chemical Properties,Usage,Production

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.

Ethyl S-4-chloro-3-hydroxybutyrate Preparation Products And Raw materials

Raw materials

Preparation Products

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Ethyl S-4-chloro-3-hydroxybutyrate Suppliers

Americas 1 Belgium 2 Canada 2 China 343 Europe 2 France 2 Germany 9 India 16 Japan 9 Slovakia 1 South Korea 2 Switzerland 3 The Netherlands 1 United Kingdom 13 United States 41 Global 447
TOKYO CHEMICAL INDUSTRY CO., LTD.
Tel
03-36680489
Fax
03-3668-0520
Email
Sales-JP@TCIchemicals.com
Country
Japan
ProdList
28398
Advantage
80
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View Lastest Price from Ethyl S-4-chloro-3-hydroxybutyrate manufacturers

ShenZhen H&D Pharmaceutical Technology Co., LTD
Product
Afatinib impurity 38 86728-85-0
Price
US $0.00-0.00/mg
Min. Order
10mg
Purity
98%
Supply Ability
500mg
Release date
2024-06-04
Henan Fengda Chemical Co., Ltd
Product
Ethyl S-4-chloro-3-hydroxybutyrate 86728-85-0
Price
US $8.00-3.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2024-04-03
Hangzhou ICH Biofarm Co., Ltd
Product
Ehyl-4-(-)chloro-3-hydroxybutyrate 86728-85-0
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1000
Release date
2023-07-05

86728-85-0, Ethyl S-4-chloro-3-hydroxybutyrateRelated Search:

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  • ethyl()-4-chloro-3-hydroxybutanoate
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  • 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
  • BUTANOIC ACID, 4-CHLORO-3-HYDROXY-, ETHYL ESTER, (S)
  • SECHB
  • Ethyl (S)-(-)-4-chloro-3-hydroxybutyrate, 97% 1GR
  • )-4-chloro-3-hydroxybutyrate
  • (S)-Ethyl 4-chloro-3-
  • AST-4
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  • Butanoic acid,4-chloro-3-hydroxy-, ethyl ester, (3S)-
  • (S) - (-) - chlorine - 4-3 - hydroxy ethyl butyrate
  • Ethyl (3S)-(-)-4-chloro-3-hydroxybutyrate
  • (S)-(-)-ETHYL-4-CHLORO 3-HYDROXYBUTANOATE
  • (S)-ETHYL 4-CHLORO-3-HYDROXYBUTYRATE
  • (S)-(-)-4-CHLORO-3-HYDROXYBUTYRIC ACID ETHYL ESTER
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  • Ethyl (3S)-4-chloro-3-hydroxybutanoate
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  • (S)-(-)-ethyl-4-chloro 3-hydroxybutanoate(ATS-4)
  • Ethyl (S)-(-)-4-chloro-3-hydroxybutyrate, 96%, ee 98%
  • Ethyl S-4-chloro-3-hydroxybutyate
  • 4-chloro-3-hydroxyhexanoate
  • (S)-4-Chloro-3-Hydroxy-Butyric Acid Enthylester
  • PEFC-026
  • Ethyl (S)-4-Chloro-3-hydroxybutyrate &gt
  • (S)-(?)-4-chL
  • oro-3-hydroxybutyrate
  • (-)-ETHYL (S)-4-CHLORO-3-HYDROXYBUTYRATE
  • Butanoic acid, 4-chloro-3-hydroxy-, ethyl ester, (3S)- (9CI, ACI)
  • 4-chloro-3-hydroxy-Butanoic acid ethyl ester (3S)- (9CI ACI)
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  • (3S)-4-Chloro-3-hydroxy-butanoic acid ethyl ester
  • Ethyl-(S)-4 chloro-3-hydroxy-Butyrarte
  • Ethyl-S-(-)chloro-3-hydroxybutyrate
  • S (-) -4-chloro-3-hydroxybutyrate ethyl ester
  • 86728-85-0
  • 96728-85-0
  • C6H11ClO3
  • Organic Building Blocks
  • Esters
  • Asymmetric Synthesis
  • Chiral Building Blocks