928-53-0

Basic information

• Product Name: (Z)-but-2-enedinitrile
• Synonyms: (Z)-but-2-enedinitrile;(Z)-2-Butenedinitrile;cis-1,2-Dicyanoethylene;Maleic acid dinitrile;Maleic nitrile;Maleonitrile;2-Butenedinitrile, (Z)-;Maleinic acid dinitrile
• CAS NO: 928-53-0
• Molecular Formula: C4H2N2
• Molecular Weight: 78.07
• Mol File: 928-53-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: 31.25°C
• Boiling Point: 130.77°C (rough estimate)
• Appearance: /
• Density: 0.9970 (rough estimate)
• Refractive Index: 1.4449
• CAS DataBase Reference: (Z)-but-2-enedinitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-but-2-enedinitrile(928-53-0)
• EPA Substance Registry System: (Z)-but-2-enedinitrile(928-53-0)

Safety Data

• Hazardous Substances Data: 928-53-0(Hazardous Substances Data)

Usage

General Description

"(Z)-but-2-enedinitrile", also known as "fumaronitrile", is an organic compound with the chemical formula C4H2N2. (Z)-but-2-enedinitrile belongs to the category of alkene nitriles. It is composed of a butene moiety which has a (Z)-configuration (meaning that the higher-priority groups are on the "same side" of the double bond), and two cyano groups (-CN) attached to the central carbon atoms of the butene. Given its structure, it possesses multiple degrees of unsaturation, contributing to its reactivity. It’s commonly used as a chemical intermediate in the synthesis of other organic compounds. This chemical is considered hazardous and may be harmful if inhaled or swallowed. It could potentially cause serious eye irritation, skin irritation, and respiratory irritation.

Upstream product

• 764-42-1 1,2-Dicyanoethylene 
• 1457-42-7 pyridazinyl-N-oxide 
• 460-19-5 ethanedinitrile 
• 107-13-1 acrylonitrile 
• 71-43-2 benzene 
• 110-82-7 cyclohexane 
• 110-61-2 butanedinitrile 
• 941-69-5 N-phenyl-maleimide 
• 1171247-70-3 BbtP=P(9-Anth) 
• 928-01-8 maleamide 
• 67-64-1 acetone 
• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 
• 7732-18-5 water 

Downstream Products

• 74-90-8 hydrogen cyanide 
• 764-42-1 butenedinitrile 
• 674289-75-9 5-fluoro-1-methyl-2,2-diphenyl-2,3-dihydropyrrole-3,4-dicarbonitrile 
• 140146-90-3 (1R,2R,3S)-3-Dimethylamino-cyclohex-4-ene-1,2-dicarbonitrile 
• 139943-15-0 (1R,2R,3R)-3-Dimethylamino-cyclohex-4-ene-1,2-dicarbonitrile 
• 764-42-1 1,2-Dicyanoethylene 
• 81052-75-7 (2S,3R,4S,5R)-2,5-Dimethyl-2,5-diphenyl-tetrahydro-furan-3,4-dicarbonitrile 
• 71870-35-4 C₄₅H₂₈N₄S 
• 71870-30-9 8,9-Dicyano-7,10-diphenylbenzopyrazolo<1,5-a>quinoline 
• 71870-24-1 2,3-Dicyano-1,4-diphenylbenzopyrazolo<1,5-a>pyridine 
• 80089-89-0 2-(2-Phenyl-benzo[d]pyrrolo[2,1-b]thiazol-3-yl)-succinonitrile 
• 80108-11-8 2-{2-Methyl-2-[3-(2-oxo-2-phenyl-ethyl)-3H-benzothiazol-(2E)-ylidenemethyl]-benzothiazol-3-yl}-1-phenyl-ethanone 
• 78113-59-4 (1S,2S,3S,3aS)-1-Benzoyl-1,2,3,3a-tetrahydro-benzo[d]pyrrolo[2,1-b]thiazole-2,3-dicarbonitrile 
• 78113-59-4 (1S,2S,3S,3aR)-1-Benzoyl-1,2,3,3a-tetrahydro-benzo[d]pyrrolo[2,1-b]thiazole-2,3-dicarbonitrile 

Relevant articles and documents

PROCESS FOR PRODUCING ISOTHIAZOLE DERIVATIVE

A process for producing 3,4-dichloro-5-cyanoisothiazole represented by a general formula (3): the process comprising: reacting a nitrile compound represented by a general formula (1): (wherein “n” denotes an integer of 0 to 2), with sulfur chloride represented by a general formula (2): [Chemical Formula 18] SmCl2 ??(2) (wherein “m” represents an integer of 1 to 2), or a mixture thereof in an aprotic polar solvent. There is provided a process for producing 3,4-dichloro-5-cyanoisothiazole, which is capable of suppressing by-production of a waste, without using a raw material having a having a strong toxicity; and is capable of providing a product having a higher purity in a high yield and efficiency in an industrial scale, in a simple manner.

2 H-azirines from a concerted addition of alkylcarbenes to nitrile groups

Photolysis of aziadamantanes in the presence of fumaronitrile (FN) unexpectedly afforded conjugated 2H-azirines resulting from addition of the carbene to the CN triple bond. This represents the first example of a direct azirine formation starting from an alkylcarbene for which a concerted pathway is postulated. The novel outcome of the reaction is favored by the prior formation of a carbene-alkene complex, a type of adduct that only recently has been described.

Lewis-acid assisted cross metathesis of acrylonitrile with functionalized olefins catalyzed by phosphine-free ruthenium carbene complex

The exchange of the PPh3 ligand in the complex [1,3-bis(2,6-dimethylphenyl)4,5-dihydroimidazol-2-ylidene](PPh 3)-(Cl)2Ru=CHPh (7) for a pyridine ligand at ambient temperature leads to the formation of the stable phosphine-free carbene ruthenium complex [1,3-bis(2,6-dimethylphenyl)4,5-dihydroimidazol-2-ylidene] (C5H5N)2(Cl)2 Ru=CHPh (8). The resulted ruthenium complex exhibits highly catalytic activity for the cross metathesis of acrylonitrile with various functionalized olefins under mild conditions, and its activity can be further improved by the addition of a Lewis acid such as Ti(O′Pr)4. In the mixture products, the Z-isomer predominates. The Royal Society of Chemistry 2005.