40915-55-7

Usage

General Description

Colorless liquid, odorless to fruity.

Reactivity Profile

The cyano group can be readily hydrolyzed in the presence of mineral acids to produce stable, moderately toxic benzoic acid . When heated to decomposition, 2-[(2-chlorophenyl)methyl]propanedinitrile emits highly toxic fumes of nitrogen oxides and hydrogen cyanide [Sax, 9th ed., 1996, p. 353]. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.

Health Hazard

Median lethal dose (mg-min/m3): 61000. Median incapacitating dose: 10 to 20. Eye/skin toxicity: Highly irritating; not toxic. Rate of action: Instantaneous. Physiological action: Highly irritating; not toxic. Detoxification rate: Rapid. (ANSER)

InChI:InChI=1/C10H7ClN2/c11-10-4-2-1-3-9(10)5-8(6-12)7-13/h1-4,8H,5H2

Upstream product

• 2698-41-1 o-chlorobenzylidene malononitrile 
• 89-98-5 2-chloro-benzaldehyde 
• 109-77-3 malononitrile 

Downstream Products

• 533928-85-7 2-(2-chlorobenzyl)-2-methylmalononitrile 

Relevant academic research and scientific papers

Preparation of O-Protected Cyanohydrins by Aerobic Oxidation of α-Substituted Malononitriles in the Presence of Diarylphosphine Oxides

A mild, reagent-cyanide-free, and efficient synthesis of O-phosphinoyl-protected cyanohydrins from readily available α-substituted malononitriles was realized using diarylphosphine oxides in the presence of O2. Mechanistic studies indicated that in addition to the initial aerobic oxidation of the malononitrile derivative notable features of this process include the formation of a tetrahedral intermediate and a subsequent intramolecular rearrangement. The phosphinoyl-protecting group can be removed by alcoholysis or by reduction with DIBAL-H.

Rh-catalyzed one-pot reductive alkylation of malononitrile under transfer hydrogenation conditions

Efficient synthesis of monosubstituted malononitriles was achieved by one-pot reductive alkylation of malononitrile with carbonyl compounds via [Cp*RhCl2]2-catalyzed transfer hydrogenation reaction.

Nanocrystalline ZnO for Knoevenagel condensation and reduction of the carbon, carbon double bond in conjugated alkenes

A novel efficient and eco-friendly nanocrystalline ZnO catalyst was used for the Knoevenagel condensation and for the reduction of C=C double bonds at room temperature in the absence of solvents.

Monosubstituted malononitriles: Efficient one-pot reductive alkylations of malononitrile with aromatic aldehydes

A powerful new one-pot method has been developed for the reductive alkylation of malononitrile with aromatic aldehydes. This new procedure has vastly improved the yield and efficiency of the process, and increased the scope of the aromatic aldehydes. Inco

Enantioselective biotransformation of α,α-disubstituted dinitriles to the corresponding 2-cyanoacetamides using Rhodococcus sp. CGMCC 0497

A new application of nitrile-converting enzymes in the synthesis of optically active α,α-disubstituted-α-cyanoacetamides from α,α-disubstituted-malononitriles with whole cells of Rhodococcus sp. CGMCC 0497 is described. The products were obtained with enantiomeric excesses of up to >99%, and yields of up to 53%. They are very useful chiral intermediates especially for the synthesis of chiral α,α-disubstituted amino acids but have never been synthesized directly by chemical or enzymatic methods.