13880-89-2

Basic information

• Product Name: 3-HYDROXYGLUTARONITRILE
• Synonyms: 3-HYDROXYGLUTARONITRILE;1,3-DICYANO-2-PROPANOL;3-HYDROXYGLUTARONITRILE 95+%;Pentanedinitrile, 3-hydroxy-
• CAS NO: 13880-89-2
• Molecular Formula: C₅H₆N₂O
• Molecular Weight: 110.11
• Mol File: 13880-89-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 203 °C / 11mmHg
• Flash Point: 203.5 °C
• Appearance: /
• Density: 1.14
• Vapor Pressure: 1.53E-08mmHg at 25°C
• Refractive Index: 1.4630-1.4660
• Storage Temp.: 0-10°C
• PKA: 12.46±0.20(Predicted)
• CAS DataBase Reference: 3-HYDROXYGLUTARONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXYGLUTARONITRILE(13880-89-2)
• EPA Substance Registry System: 3-HYDROXYGLUTARONITRILE(13880-89-2)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 3276
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 13880-89-2(Hazardous Substances Data)

Usage

General Description

3-Hydroxyglutaronitrile is a chemical compound with the molecular formula C4H7NO. It is a colorless liquid with a boiling point of 193-195°C. 3-Hydroxyglutaronitrile is primarily used in the synthesis of pharmaceuticals and agrochemicals, specifically as a precursor in the production of gamma-hydroxybutyric acid (GHB), a central nervous system depressant. It is also used as a building block for the synthesis of various other organic compounds. 3-Hydroxyglutaronitrile is considered a hazardous chemical and should be handled and stored with proper safety precautions.

InChI:InChI=1/C5H6N2O/c6-3-1-5(8)2-4-7/h5,8H,1-2H2

Upstream product

• 105-33-9 4-chloro-3-hydroxybutyronitrile 
• 151-50-8 potassium cyanide 
• 64-17-5 ethanol 
• 96-23-1 1,3-Dichloro-2-propanol 
• 143-33-9 sodium cyanide 
• 106-89-8 epichlorohydrin 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 624-58-8 3,4-epoxybutanenitrile 
• 67843-74-7 (S)-epichlorohydrin 
• 7677-24-9 trimethylsilyl cyanide 

Downstream Products

• 32328-03-3 diethyl 3-hydroxyglutarate 
• 5382-16-1 4-HYDROXYPIPERIDINE 
• 38595-00-5 1,5-diamino-3-hydroxypentane 
• 1724-02-3 glutaconic acid 
• 138145-58-1 3-O-(benzoyl)-glutaronitrile 
• 287955-93-5 (R)-3-hydroxy-4-cyano-butyric acid 
• 1364524-02-6 (4-(6-amino-3,5-dichloropyridin-2-yl)piperazin-1-yl)(3-(2-methoxyphenyl)-5-methylisoxazol-4-yl)methanone 
• 1206248-85-2 tert-butyl 4-(6-aminopyridin-2-yl)piperazine-1-carboxylate 
• 1364524-03-7 di-tert-butyl 4,4'-(pyridine-2,6-diyl)dipiperazine-1-carboxylate 
• 147028-51-1 4-cyano-3-hydroxybutanoic acid 
• 158008-69-6 3-hydroxybutyric acid 
• 4045-22-1 N-acetyl-4-hydroxypiperidine 
• 106-52-5 N-methyl-4-hydroxypiperidine 
• 90633-18-4 4-bromo-1H-piperidine 

Relevant articles and documents

PROCESS FOR THE SYNTHESIS OF 3-HYDROXYGLUTARONITRILE

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Nitrilase-catalysed desymmetrisation of 3-hydroxyglutaronitrile: Preparation of a statin side-chain intermediate

An efficient, scaleable synthesis of ethyl (R)-4-cyano-3-hydroxybutyrate, a potential intermediate in the synthesis of Atorvastatin (Lipitor), has been developed. The three-stage process starts with reaction of low-cost epichlorohydrin with cyanide to give 3-hydroxyglutaronitrile (3-HGN). The second stage utilises a nitrilase-catalysed desymmetrisation of 3-HGN. The nitrilase reaction has been optimized to work at 3 M (330 g/L) substrate concentration, pH 7.5,27 °C. Under these conditions, with an enzyme loading of 6 wt %, 100% conversion and 99% ee product is obtained in 16 h. This material is then esterified to give the target compound, ethyl (R)-4-cyano-3-hydroxybutyrate. The cost-effectiveness of the process is determined by three factors: use of a low-cost starting material, the introduction of the chiral centre by desymmetrisation as opposed to kinetic resolution, and the use of Pfenex Expression Technology to allow a lower-cost supply of biocatalyst.

PROCESSES FOR MAKING (R)-ETHYL 4-CYANO-3-HYDROXYBUTYRIC ACID

The invention provides novel processes for making ethyl-4-cyano-3-hydroxybutyrate, e.g., (R)-ethyl 4-cyano-3-hydroxybutyric acid, and 4-cyano-3-hydroxybutyric acid. The invention provides protocols for making and 4-cyano-3-hydroxybutyric acid and ethyl-4-cyano-3-hydroxybutyrate by whole cell processes, cell lysate processes, "one pot processes" and "multi-pot" processes using a variety of parameters.