108005-47-6

Basic information

• Product Name: 2-(4-chlorophenyl)succinonitrile
• Synonyms: 2-(4-chlorophenyl)succinonitrile
• CAS NO: 108005-47-6
• Molecular Weight: 190.632
• Mol File: 108005-47-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-(4-chlorophenyl)succinonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-chlorophenyl)succinonitrile(108005-47-6)
• EPA Substance Registry System: 2-(4-chlorophenyl)succinonitrile(108005-47-6)

Safety Data

• Hazardous Substances Data: 108005-47-6(Hazardous Substances Data)

Upstream product

• 773837-37-9 sodium cyanide 
• 127604-92-6 dimethyl 2-(4-chlorophenyl)cyclopropane-1,1-dicarboxylate 
• 104-88-1 4-chlorobenzaldehyde 
• 7677-24-9 trimethylsilyl cyanide 
• 101671-01-6 1-nitro-2-(4-chlorophenyl)ethylene 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 764-42-1 1,2-Dicyanoethylene 
• 2286-35-3 ethyl 3-(4-chlorophenyl)-2-cyanoacrylate 
• 143-33-9 sodium cyanide 

Downstream Products

• 120418-62-4 3-(4-chlorophenyl)pyrrolidine 

Relevant articles and documents

Ring Opening of Donor-Acceptor Cyclopropanes with Cyanide Ion and Its Surrogates

A straightforward method for ring opening of donor-acceptor cyclopropanes with trimethylsilyl cyanide as a surrogate of cyanide ion in the presence of B(C6F5)3 or trifluoromethanesulfonic acid as a catalyst has been developed. The methodology provides a short route to γ-cyanoesters that can be useful synthetic intermediates for the synthesis of diverse bioactive molecules such as glutaric and δ-aminovaleric acid derivatives, 3-arylpiperidines, or other substituted phenethylamines. Oppositely, the attempts to synthesize these γ-cyanoesters by direct reaction of cyclopropanes with sodium cyanide under typical SN2 conditions led to the formation of 2-arylsuccinonitriles.

Metabolism of 3-(p-chlorophenyl)pyrrolidine. Structural effects in conversion of a prototype γ-aminobutyric acid prodrug to lactam and γ-aminobutyric acid type metabolites

By use of rat liver or brain homogenate supernatants containing microsomes and/or mitochondria, it was found that the prototype GABAergic prodrug [3-(p-chlorophenyl)pyrrolidine (1) underwent a series of α-oxidation transformations to a pair of amino acid metabolites and a pair of lactam metabolites [4-amino-3-(p-chlorophenyl)butanoic acid, baclofen (5); 4-amino-2-(p-chlorophenyl)butanoic acid (10); 4-(chlorophenyl)pyrrolidin-2-one (6); and 3-(p-chlorophenyl)pyrrolidine-2-one (11)]. With the liver homogenates, the formation of the lactam metabolites was approximately 2 orders of magnitude greater than that of the amino acid metabolites, while with the brain homogenates, the amino acid and lactam pathways were of similar magnitude. For either tissue, for both the lactam and the amino acid series, attack at the less sterically hindered 5-position of the pyrrolidine ring was greater than the attack at the 2-position (5>10 and 6>11) with the exception of the liver homogenate mitochondrial fraction (611). The parenteral administration of the prodrug 1 was found to give detectable brain levels of 5 as well as activity in an isoniazid-induced (GABA-inhibited) convulsion model.