4172-99-0

Basic information

• Product Name: 1-CYANOCYCLOHEXANE ACETONITRILE
• Synonyms: 1-CYANOCYCLOHEXANE ACETONITRILE;1-Cyanomethyl-1-cyclohexanenitril;Gabapentin Related Compound B;1-Cyanomethyl-1-cyclohexanenitrile;Gabapentin Related Bis-nitrile;Gabapentin Di-Nitrile IMpurity;1-(CyanoMethyl)cyclohexanecarbonitrile
• CAS NO: 4172-99-0
• Molecular Formula: C₉H₁₂N₂
• Molecular Weight: 148.2
• Product Categories: Aromatic Nitriles;Heterocyclic Compounds;Intermediates & Fine Chemicals;Neurochemicals;Pharmaceuticals
• Mol File: 4172-99-0.mol

Chemical Properties

• Melting Point: 84-86°C
• Boiling Point: 319.74 °C at 760 mmHg
• Flash Point: 154.27 °C
• Appearance: White to Off-White Solid
• Density: 1.00
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.478
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 1-CYANOCYCLOHEXANE ACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CYANOCYCLOHEXANE ACETONITRILE(4172-99-0)
• EPA Substance Registry System: 1-CYANOCYCLOHEXANE ACETONITRILE(4172-99-0)

Safety Data

• Hazardous Substances Data: 4172-99-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Cyanocyclohexane acetonitrile is used as a key intermediate in the synthesis of Gabapentin, an anticonvulsant and analgesic medication. It is utilized for the production of this drug due to its ability to react with other compounds to form the desired active pharmaceutical ingredient (API). This makes 1-Cyanocyclohexane acetonitrile an essential component in the development and manufacturing process of Gabapentin.
Additionally, 1-Cyanocyclohexane acetonitrile may also be used as an intermediate in the synthesis of other pharmaceuticals and chemicals, depending on its reactivity and the specific requirements of the target compounds. Its versatility in chemical reactions makes it a valuable asset in the development of new medications and industrial applications.

InChI:InChI=1/C9H12N2/c10-7-6-9(8-11)4-2-1-3-5-9/h1-6H2

Upstream product

• 51939-79-8 ethyl 2-cyano-2-(1-cyanocyclohexyl)acetate 
• 55568-06-4 methyl 2-cyano-2-cyclohexylideneacetate 
• 151-50-8 potassium cyanide 
• 931-97-5 1-hydroxy-1-cyclohexanecarbonitrile 
• 18852-51-2 sodium cyanoacetic acid ethyl ester 
• 861342-83-8 (1-carbamoyl-cyclohexyl)-cyano-acetic acid 
• 773837-37-9 sodium cyanide 
• 6802-76-2 ethyl 2-cyano-2-cyclohexylideneacetate 
• 108-94-1 cyclohexanone 
• 105-34-0 methyl 2-cyanoacetate 
• 143-33-9 sodium cyanide 

Downstream Products

• 861315-79-9 (1-carbamoyl-cyclohexyl)-acetic acid amide 
• 60142-96-3 H-Gpn-OH 
• 133481-10-4 (1-Cyanocyclohexyl)acetic acid ethyl ester 
• 134873-54-4 benzyl (1-cyanocyclohexyl)acetate 
• 64744-50-9 gabapentin-lactam 
• 3187-28-8 1-Hydroxymethyl-1-(2-hydroxyaethyl)-cyclohexan 
• 133481-09-1 (1-cyanocyclohexyl)-acetic acid 
• 4442-85-7 2-cyclohexylethylamine 
• 67950-95-2 1-carboxycyclohexylacetic acid 
• 25564-89-0 2,2-Dichlor-3,3-pentamethylen-succinonitril 
• 55007-87-9 3-(1-carboxy-cyclohexyl)-pyruvic acid 

Relevant articles and documents

Bis-morpholinophosphorylchloride, a novel reagent for the conversion of primary amides into nitriles

Bis-morpholinophosphorylchloride (Bmpc), in the presence of a base, is an efficient dehydrating agent for both aromatic and aliphatic primary amides, and gives corresponding nitriles under mild conditions in god yields and purity. During the reaction the enantiomeric integrity remains intact.

Preparation method of 1-cyanocyclohexyl acetonitrile

The invention provides a method for preparing 1-cyanocyclohexyl acetonitrile by a 'one-pot method', which mainly comprises the following steps: reacting cyclohexanone with alkyl cyanoacetate in the presence of weak base salt and optional acid in a proper organic solvent; after the reaction is completed, adding cyanide, water and a phase transfer catalyst into the reaction system without treatment,and continuing the reaction to obtain 1-cyanocyclohexyl acetonitrile. According to the 1-cyanocyclohexyl acetonitrile obtained by the method, the purity and yield of the product are greatly improved,and the method is low in production cost, simple to operate and suitable for industrial production.

A PROCESS FOR THE PREPARATION OF GABAPENTIN

The present invention provides an improved process for the preparation of a compound of formula (I),

Nitrilase-catalyzed selective hydrolysis of dinitriles and green access to the cyanocarboxylic acids of pharmaceutical importance

To further explore its synthetic applications, the nitrilase bll6402 from Bradyrhizobium japonicum strain USDA110 has been examined toward the hydrolysis of various dinitriles. It has been found that nitrilase bll6402 effectively hydrolyzed α,ω-dinitriles to ω-cyanocarboxylic acids, and the selectivity was independent of the substrate chain length. This feature is distinct from all the known nitrilases of various sources. Nitrilase bll6402 was thus applied to the synthesis of 1-cyanocycloalkaneacetic acids, the useful precursors for the synthesis of gabapentin and its analogues.

Carboxylate bioisosteres of gabapentin

A series of carboxylate bioisosteres of structures related to gabapentin 1 have been prepared. When the carboxylate was replaced by a tetrazole, this group was recognized by the α2-δ protein. Further characterization of α2-δ binding compounds 14a and 14b revealed a similar pattern of functional in vitro and in vivo activity to gabapentin 1.

Composes heterocycliques spiranniques. V. Synthese et etude configurationnelle dans la serie de l'oxa-2 spirodecane

The 8-t-butyl-2-oxaspirodecan-3-one, 8-t-butyl-2-oxaspirodecane and its 3-methylated derivatives were synthesized by different routes starting from methyl 4-t-butylcyclohexanecarboxylate, 4-t-butylmethylenecyclohexane and methyl 4-t-butylcyclohexylidenecyanoacetate.The cis (-CH2O axial) and trans (-CH2O equatorial) isomers were isolated by preparative HPLC ; their configurations were established from (1) the known stereoselectivity of the reaction involved in the cis/trans ratio controlling step (2) their proton and 13C nmr spectra.