1557-59-1

Usage

Uses

Used in Chemical Synthesis:
cis,cis-Mucononitrile is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows it to participate in a range of chemical reactions, making it a valuable building block for the creation of new molecules and materials.
Used in the Production of Dinitriles:
cis,cis-Mucononitrile is used as a starting material for the production of dinitriles, which are important in the synthesis of various chemicals and polymers. These dinitriles can be further modified or reacted to create a wide array of products with diverse applications.
Used in the Synthesis of Dinitriles with Specific Properties:
The Pt-catalyzed addition of diethylphosphine to cis,cis-mucononitrile yields a new diphosphine, Et2PCH(CN)CH(CH2CH2CN)PEt2. This reaction demonstrates the versatility of cis,cis-mucononitrile in creating compounds with specific properties, such as the formation of diphosphines with potential applications in catalysis and coordination chemistry.

Synthesis Reference(s)

Journal of the American Chemical Society, 87, p. 1147, 1965 DOI: 10.1021/ja01083a047

InChI:InChI=1/C6H4N2/c7-5-3-1-2-4-6-8/h1-4H/b3-1-,4-2-

Upstream product

• 71-43-2 benzene 
• 110-82-7 cyclohexane 
• 95-54-5 1,2-diamino-benzene 
• 762-42-5 dimethyl acetylenedicarboxylate 

Downstream Products

• 124-09-4 1,6-Hexanediamine 

Relevant academic research and scientific papers

Hypervalent iodine(iii)-induced oxidative [4+2] annulation of o-phenylenediamines and electron-deficient alkynes: Direct synthesis of quinoxalines from alkyne substrates under metal-free conditions

Hypervalent iodine(iii)-induced oxidative [4+2] annulation of o-phenylenediamines and electron-deficient alkynes under metal-free conditions has been developed. The reaction allows for direct access to quinoxalines bearing two electron-withdrawing groups in an efficient manner.

AMMOXYDATION CATALYTIQUE DES HYDROCARBURES ET REACTIONS APPARENTEES. XXII. AMMOXYDATION DU BENZENE ET DU CYCLOHEXANE

Benzene ammoxidation at 440-550 deg C/1 at. produces, on V-Mo, Ti-Mo, Bi-Mo (oxides) catalysts, unsaturated C4 (maleo and fumaronitriles) and C6 (mucononitrile and stereoisomers) dinitriles.These initial selectivities fall with increasing conversions, and C6 dinitriles disappear above 10percent conversion by thermal or catalytic degradation.The main initial stereoisomer cis-cis (mucononitrile) is consistent with a 1-2 attack of the aromatic ring, so far unknown in catalytic oxidations.Cyclohexane ammoxidation goes through the oxidative dehydrogenation to benzene and proceduces small amounts of C4 unsaturated dinitriles along with traces of C4, C5 and C6 saturated dinitriles coming from a different reaction path.In both cases, V-Mo and Ti-Mo are the best catalysts for dinitriles production; no C6 formed on Sn-Mo, Sb-Mo and Sn-Sb-Fe-catalysts.