1089675-68-2

Basic information

• Product Name: 3-hydroxy-2,2-dimethyl-4-oxo-3,4-diphenylbutyronitrile
• Synonyms: 3-hydroxy-2,2-dimethyl-4-oxo-3,4-diphenylbutyronitrile
• CAS NO: 1089675-68-2
• Molecular Weight: 279.338
• Mol File: 1089675-68-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-hydroxy-2,2-dimethyl-4-oxo-3,4-diphenylbutyronitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-2,2-dimethyl-4-oxo-3,4-diphenylbutyronitrile(1089675-68-2)
• EPA Substance Registry System: 3-hydroxy-2,2-dimethyl-4-oxo-3,4-diphenylbutyronitrile(1089675-68-2)

Safety Data

• Hazardous Substances Data: 1089675-68-2(Hazardous Substances Data)

Upstream product

• 78-67-1 2,2'-azobis(isobutyronitrile) 
• 1089675-66-0 C₁₈H₂₀O₃ 
• 1089675-65-9 C₂₂H₁₇NO₃ 
• 1089675-64-8 C₂₂H₂₀O₃ 
• 53151-59-0 C₂₁H₁₈O₃ 

Relevant articles and documents

Key role of Ti(IV) in the selective radical - radical cross-coupling mediated by the ingold-Fischer effect

We report an innovative approach for the selective synthesis of polyfunctional derivatives by cross-combination of different radicals generated under mild conditions. The coordinating effect of Ti(IV) plays a key role in the reaction mechanism: due to its chelating action on the hydroxyl groups, it promotes the homolytic C-C bond cleavage of α,β-dihydroxy ketones by enhancing the captodative effect and the consequent stabilization of the corresponding α-hydroxy-α-carbonyl radicals. When these radicals are generated in the presence of stoichiometric amounts of TiCl4 and 2,2'-azo-bis-isobutyronitrile (AIBN) is employed as a source of α-cyanoisopropyl radicals, the selective radical-radical cross-coupling is observed, affording the corresponding β-hydroxynitriles in high yields. This innovative methodology allows application of the well-known Ingold-Fischer effect to a wider range of stabilized carbon-centered radicals, whose formation derives from the chelating action of Ti(IV).