| Identification | More | [Name]
Ethyl S-4-chloro-3-hydroxybutyrate | [CAS]
86728-85-0 | [Synonyms]
BUTANOIC ACID, 4-CHLORO-3-HYDROXY-, ETHYL ESTER, (S)
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
(S)-(-)-4-CHLORO-3-HYDROXYBUTYRIC ACID ETHYL ESTER
(S)-4-CHLORO-3-HYDROXYBUTYRIC ACID ETHYL ESTER
(S)-4-CHLORO-3-HYDROXY-N-BUTYRIC ACID ETHYL ESTER
SECHB
(S)-(-)-ETHYL-4-CHLORO 3-HYDROXYBUTANOATE
(S)-ETHYL 4-CHLORO-3-HYDROXYBUTYRATE
ethyl()-4-chloro-3-hydroxybutanoate
Ethyl(S)-4-chloro-3-hydroxybutylate
S-4-Chloro-3-hydroxybutyrate
Ehyl-4-(-)chloro-3-hydroxybutyrate
Ethyl (S)-(-)-4-chloro-3-hydroxybutyrate, 96% (97% EE/GLC)
(2R,4R)-2,4-PENTANEDIOL EE 99+%
Ethyl(S)-(-)-4-chloro-3-Hydrox
ETHYL(S)-4-CHLORO-3-HYDROXY-BUTYRATE/ATS-4 | [EINECS(EC#)]
617-912-5 | [Molecular Formula]
C6H11ClO3 | [MDL Number]
MFCD00211241 | [Molecular Weight]
166.6 | [MOL File]
86728-85-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless to light yellow liqui | [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.)
| [Fp ]
109 °C
| [storage temp. ]
Refrigerator | [form ]
Liquid | [pka]
13.23±0.20(Predicted) | [color ]
Clear colorless to yellow | [Optical Rotation]
[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) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS05,GHS07 | [Signal word ]
Danger | [Hazard statements ]
H302-H318 | [Precautionary statements ]
P280-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R41:Risk of serious damage to eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S39:Wear eye/face protection . | [RIDADR ]
2810 | [WGK Germany ]
3
| [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29181990 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Dam. 1 |
| Hazard Information | Back Directory | [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.
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