21456-03-1

Basic information

• Product Name: 2-cyano-3-(4-bromophenyl)propionitrile
• Synonyms: 2-cyano-3-(4-bromophenyl)propionitrile
• CAS NO: 21456-03-1
• Molecular Weight: 235.083
• Mol File: 21456-03-1.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 2-cyano-3-(4-bromophenyl)propionitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-cyano-3-(4-bromophenyl)propionitrile(21456-03-1)
• EPA Substance Registry System: 2-cyano-3-(4-bromophenyl)propionitrile(21456-03-1)

Safety Data

• Hazardous Substances Data: 21456-03-1(Hazardous Substances Data)

Upstream product

• 3001-72-7 DBN 
• 2826-24-6 4-bromobenzylidenemalononitrile 
• 109-77-3 malononitrile 
• 1122-91-4 4-bromo-benzaldehyde 
• 2637-34-5 2-Sulfanylpyridine 
• 70146-78-0 diethyl 2-(4-bromobenzyl)malonate 

Downstream Products

• 57775-08-3 3-(4-Bromo-phenyl)-propionitrile 
• 21448-05-5 2-benzyl-2-(4-bromophenyl)malononitrile 
• 1607831-67-3 C₁₀H₁₁BrN₄ 
• 1607831-16-2 [8-(4-bromo-benzyl)-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrazolo[1,5-a][1,3,5]triazin-7-yl]thiourea 
• 1607831-41-3 C₁₈H₂₁BrN₆O₄S₂ 
• 2826-24-6 4-bromobenzylidenemalononitrile 
• 1419180-96-3 2,2-bis(4-bromobenzyl)malononitrile 

Relevant articles and documents

Catalyst-Free [3 + 3] Annulation/Oxidation of Cyclic Amidines with Activated Olefins: When the Substrate Olefin Is Also an Oxidant

Herein we describe a catalyst-free regioselective [3 + 3] annulation/oxidation reaction of cyclic amidines such as DBU (1,8-diazabicyclo(5.4.0)undec-7-ene) and DBN (1,5-diazabicyclo(4.3.0)non-5-ene) with activated olefins, i.e., 2-arylidenemalononitriles and 2-cyano-3-aryl acrylates, to afford tricyclic 2-pyridones and pyridin-2(1H)-imines, respectively. The mechanism has been proposed based on DFT calculations. In the reaction, the cyclic amidines serve as C,N-bisnucleophiles for the cyclization, while the olefins play a dual role by acting as both reactants and oxidants.

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.

Synthesis and biocatalytic ene-reduction of Knoevenagel condensation compounds by the marine-derived fungus Penicillium citrinum CBMAI 1186

The chemoselective bioreduction of α,β-unsaturated compounds is an important synthetic tool that can have applications in the synthesis of many fine chemicals and pharmaceutical molecules. The synthesis of aromatic malononitrile derivatives through Knoevenagel condensation by microwave radiation under green chemistry conditions using methanol like solvent, free base and free catalyst is here reported. In addiction the biocatalytic reduction of the C–C double bond of aromatic malononitrile derivatives by whole cells of the marine-derived fungal Penicillium citrinum CBMAI 1186 was also tested. The products catalyzed by the fungus ene-reductase were obtained in very good yields (up to >98%).