3779-31-5

Basic information

• Product Name: Propanedinitrile, bis(phenylmethyl)-
• Synonyms: dibenzylmalononitrile;dibenzyl-malononitrile;dibenzylcyanomalonate;Dibenzyl-malononitril
• CAS NO: 3779-31-5
• Molecular Formula: C17H14N2
• Molecular Weight: 246.312
• Mol File: 3779-31-5.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: Propanedinitrile, bis(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Propanedinitrile, bis(phenylmethyl)-(3779-31-5)
• EPA Substance Registry System: Propanedinitrile, bis(phenylmethyl)-(3779-31-5)

Safety Data

• Hazardous Substances Data: 3779-31-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 26, p. 4112, 1961 DOI: 10.1021/jo01068a605

Upstream product

• 22800-68-6 2-Aminocarbonyl-2-cyano-1,3-diphenylpropane 
• 100-44-7 benzyl chloride 
• 109-77-3 malononitrile 
• 2700-22-3 Benzylidenemalononitrile 
• 100-39-0 benzyl bromide 
• 5362-78-7 dimethylsulfonium dicyanomethylide 
• 98-88-4 benzoyl chloride 

Downstream Products

• 119-61-9 benzophenone 
• 53097-56-6 2-benzyl-3-phenylpropionitrile 
• 6624-04-0 2-benzyl-1,3-diphenyl-propan-1-one 
• 101292-78-8 2-benzyl-3-phenylpropanamide 
• 355145-09-4 2-benzyl-3-phenyl-propylamine 
• 22800-68-6 2-Aminocarbonyl-2-cyano-1,3-diphenylpropane 
• 259743-70-9 2-benzyl-2-methyl-3-phenylpropanenitrile 
• 186001-28-5 2,2-dibenzylpropane-1,3-diamine 
• 444575-98-8 (4S)-2,2'-(1-phenylmethyl-2-phenylethylidene)bis[4-(1-methylethyl)-4,5-dihydrooxazole] 
• 529508-28-9 2,2-dibenzyl-3-furan-2-yl-3-hydroxy-propionitrile 
• 77526-59-1 C₃₅H₂₉AsN₂O 

Relevant articles and documents

Selective Synthesis of β-Ketonitriles via Catalytic Carbopalladation of Dinitriles

A practical, convenient, and highly selective method of synthesizing β-ketonitriles from the Pd-catalyzed addition of organoboron reagents to dinitriles has been developed. This method provides excellent functional-group tolerance, a broad scope of substrates, and the convenience of using commercially available substrates. The method is expected to show further utility in future synthetic procedures.

Titanium(III)-Catalyzed Reductive Decyanation of Geminal Dinitriles by a Non-Free-Radical Mechanism

A titanium-catalyzed mono-decyanation of geminal dinitriles is reported. The reaction proceeds under mild conditions, tolerates numerous functional groups, and can be applied to quaternary malononitriles. A corresponding desulfonylation is demonstrated as well. Mechanistic experiments support a catalyst-controlled cleavage without the formation of free radicals, which is in sharp contrast to traditional stoichiometric radical decyanations. The involvement of two TiIII species in the C?C cleavage is proposed, and the beneficial role of added ZnCl2 and 2,4,6-collidine hydrochloride is investigated.

A one-pot electrophilic cyanation–functionalization strategy for the synthesis of disubstituted malononitriles

Malononitriles are valuable synthetic intermediates for many applications, including the synthesis of herbicides and other biologically active molecules, and the synthesis of chiral ligands for asymmetric catalysis. This article describes the development of a procedure for the conversion of primary nitriles to malononitriles using dimethylmalononitrile, a commercial, non-toxic, carbon-bound source of electrophilic cyanide. This procedure avoids the use of toxic cyanide or malononitrile as a starting material. This protocol is further applied to the dicyanation of benzyl Grignard reagents, generated from benzyl bromides, yielding fully functionalized malononitriles from a nitrile-free precursor.