127913-44-4

Basic information

• Product Name: (S)-4-Chloro-3-hydroxybutyronitrile
• Synonyms: 4-CHLORO-3-HYDROXY-BUTYRONITRILE;(S)-(-)-4-CHLORO-3-HYDROXYBUTYRONITRILE;(S)-4-CHLORO-3-HYDROXYBUTYRONITRILE;(S)-(-)-4-CHLORO-3-HYDROXYBUTYRONITRILE, 97% (97% EE/GLC);(S)-4-CHLORO-3-HYDROXYBUTYRONITRILE 98+%;(S)-(-)-4-Chloro-3-hydroxybutyronitrile, 97%, ee 98%;(S)-4-Chloro-3-hydro;S-(-)-4-chloro-3-hydorxy butyronitrile
• CAS NO: 127913-44-4
• Molecular Formula: C₄H₆ClNO
• Molecular Weight: 119.55
• EINECS: 1308068-626-2
• Product Categories: chiral
• Mol File: 127913-44-4.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 110 °C/1 mmHg(lit.)
• Flash Point: 110 °C
• Appearance: colorless to light yellow liquid
• Density: 1.250 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.000304mmHg at 25°C
• Refractive Index: n20/D 1.474(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 12.67±0.20(Predicted)
• CAS DataBase Reference: (S)-4-Chloro-3-hydroxybutyronitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-Chloro-3-hydroxybutyronitrile(127913-44-4)
• EPA Substance Registry System: (S)-4-Chloro-3-hydroxybutyronitrile(127913-44-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 127913-44-4(Hazardous Substances Data)

Usage

Description

(S)-4-Chloro-3-hydroxybutyronitrile, also known as (3S)-4-Chloro-3-hydroxybutyronitrile, is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceutical compounds. It is a colorless to light yellow liquid with unique chemical properties that make it valuable in the pharmaceutical industry.

Uses

Used in Pharmaceutical Synthesis:
(S)-4-Chloro-3-hydroxybutyronitrile is used as an intermediate in the synthesis of hydroxypyrrolidinones, which are further utilized as carbapenem precursors. Carbapenems are a class of beta-lactam antibiotics known for their broad-spectrum activity against various bacteria, including those resistant to other antibiotics.
(S)-4-Chloro-3-hydroxybutyronitrile is also used in the preparation of atorvastatin (A791750) precursors. Atorvastatin is a widely prescribed drug for lowering cholesterol levels and reducing the risk of cardiovascular diseases.
Additionally, (S)-4-Chloro-3-hydroxybutyronitrile is an impurity in the synthesis of Rosuvastatin (R700500), a selective, competitive HMG-CoA reductase inhibitor. Rosuvastatin is a potent cholesterol-lowering drug that helps in the management of hyperlipidemia and prevention of cardiovascular events.
Used in Antilipemic Applications:
(S)-4-Chloro-3-hydroxybutyronitrile has antilipemic properties, making it a potential candidate for the development of new drugs targeting hyperlipidemia, a condition characterized by high levels of lipids in the blood, which can increase the risk of cardiovascular diseases.

InChI:InChI=1/C4H6ClNO/c5-3-4(7)1-2-6/h4,7H,1,3H2/t4-/m0/s1

Upstream product

• 96-23-1 1,3-Dichloro-2-propanol 
• 151-50-8 potassium cyanide 
• 29331-43-9 4-chloro-3-acetoxybutyronitrile 
• 773837-37-9 sodium cyanide 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 105-33-9 4-chloro-3-hydroxybutyronitrile 
• 106-89-8 epichlorohydrin 
• 146864-19-9 (2RS,4S)-2-oxo-4-chloromethyl-1,3,2-dioxathiolane 
• 67843-74-7 (S)-epichlorohydrin 
• 143-33-9 sodium cyanide 
• 7677-24-9 trimethylsilyl cyanide 

Downstream Products

• 122536-94-1 (S)-3-hydroxypyrrolidine hydrochloride 
• 1269363-97-4 (R)-3-chloro-1-cyanopropan-2-yl 4-chlorobenzoate 
• 10488-69-4 ethyl (S)-4-chloro-3-hydroxybutanoate 
• 727382-14-1 (3S)-4-chloro-3-[(trimethylsilyl)oxy]butyronitrile 
• 1419874-04-6 (S)-3-hydroxy-4-[(1-phenyltetrazole-5-yl)sulfanyl]butyronitrile 
• 100243-39-8 3-hydroxypyrrolidine 
• 635724-49-1 tert-butyl (2S,4S)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-phenylpyrrolidine-1-carboxylate 

Relevant articles and documents

A One-Step Biocatalytic Process for (S)-4-Chloro-3-hydroxybutyronitrile using Halohydrin Dehalogenase: A Chiral Building Block for Atorvastatin

(S)-4-Chloro-3-hydroxybutyronitrile [(S)-CHBN] was used as a chiral building block for the preparation of atorvastatin. In this study, (R,S)-epichlorohydrin [(R,S)-ECH] and 1,3-dichloro-2-propanol (1,3-DCP) were investigated to prepare (S)-CHBN by using the halohydrin dehalogenase HheC from Agrobacterium radiobacter AD1. Preparing (S)-CHBN from (R,S)-ECH gave a modest enantiomeric excess (ee), whereas by using 1,3-DCP as the substrate, (S)-CHBN was obtained with 97.3 % ee after pH optimization. However, a low ee value and low yield of (S)-CHBN were obtained if the substrate concentration was increased to 10 g L-1. To obtain a higher ee value and yield, 16 mutants were constructed and screened. The variant W249F with improvements in activity and enantioselectivity was identified and applied at a 1,3-DCP loading of 10 g L-1, which gave (S)-CHBN in 86 % yield with 97.5 % ee in 1 h. This is the first report of a one-step biocatalytic process for the preparation of (S)-CHBN from prochiral 1,3-DCP.

Method for synthesizing high-content (S)-4-chloro-3-hydroxybutyronitrile

The invention relates to a method for synthesizing high-content (S)-4-chloro-3-hydroxybutyronitrile. The method comprises the following step: by taking S-type epoxy chloropropane as a reaction substrate and trimethylsilyl cyanide as a cyaniding agent in the presence of water, obtaining the (S)-4-chloro-3-hydroxybutyronitrile. According to the invention, traditional sodium cyanide or hydrogen cyanide is not used as a cyaniding agent, so that potential safety hazards in production are avoided, harsh production conditions are not needed, cyanide-containing wastewater is not generated, the wastewater treatment cost of enterprises is reduced, side reactions are reduced, the yield of target products is increased, and the subsequent purification difficulty is reduced; and the method further optimizes the molar ratio of the catalyst to the reaction substrate to the cyaniding agent to water to the catalyst, the reaction time, the reaction temperature and other conditions so as to further reduce the probability of side reaction, and improve the yield and the purity of the product.

Method for synthesizing butyrolactone derivative

The invention discloses a method for synthesizing a butyrolactone derivative. The method comprises steps as follows: (1), after being activated by a titanium reagent, an epoxy compound represented asa formula (II) is subjected to an addition reaction by a Grignard reagent, and a compound represented as a formula (III) is obtained; (2), the compound represented as the formula (III) is subjected tocyano hydrolysis under the alkaline condition, and a carboxylic acid derivative represented as a formula (IV) is obtained; (3), the carboxylic acid derivative represented as the formula (IV) is subjected to a dehydration cyclization reaction, and the butyrolactone derivative represented as a formula (I) is obtained. The method has the advantages of being simple in synthesis step, low in production cost and high in functional group selectivity, regioselectivity and yield; the synthetic route is shown in the description.