ChemicalBook > CAS DataBase List > Ethyl S-4-chloro-3-hydroxybutyrate

Ethyl S-4-chloro-3-hydroxybutyrate

CAS No.86728-85-0
Chemical Name:Ethyl S-4-chloro-3-hydroxybutyrate
CBNumber:CB9448087
Molecular Formula:C6H11ClO3
Formula Weight:166.6
MOL File:86728-85-0.mol

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
pka 13.23±0.20(Predicted)
form Liquid
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)
UNSPSC Code 12352101
NACRES NA.22

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

NFPA 704:

	0
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H302-H318
Precautionary statements P280-P305+P351+P338

Ethyl S-4-chloro-3-hydroxybutyrate Price More Price(6)

Brand: Sigma-Aldrich
Product number: 460524
Product name : Ethyl (S)-(−)-4-chloro-3-hydroxybutyrate
Purity: 96%
Packaging: 1G
Price: ₹2782.03
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 460524
Product name : Ethyl (S)-(−)-4-chloro-3-hydroxybutyrate
Purity: 96%
Packaging: 1G
Price: ₹2782.03
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich
Product number: 460524
Product name : Ethyl (S)-(−)-4-chloro-3-hydroxybutyrate
Purity: 96%
Packaging: 5G
Price: ₹9428.58
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 460524
Product name : Ethyl (S)-(−)-4-chloro-3-hydroxybutyrate
Purity: 96%
Packaging: 5G
Price: ₹9428.58
Updated: 2022/06/14
Buy: Buy

Brand: TCI Chemicals (India)
Product number: C1717
Product name : Ethyl (S)-4-Chloro-3-hydroxybutyrate
Purity: min. 95.0 %
Packaging: 5G
Price: ₹10100
Updated: 2022/05/26
Buy: Buy

Ethyl S-4-chloro-3-hydroxybutyrate Chemical Properties,Usage,Production

Chemical Properties Colorless to light yellow liqui
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.
Uses Atorvastatin Intermediate
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.