225918-54-7

Basic information

• Product Name: (S)-α-(2-chlorophenyl)-α-[(diphenylmethyl)amino]acetonitrile
• Synonyms: (S)-α-(2-chlorophenyl)-α-[(diphenylmethyl)amino]acetonitrile
• CAS NO: 225918-54-7
• Molecular Weight: 332.832
• Mol File: 225918-54-7.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (S)-α-(2-chlorophenyl)-α-[(diphenylmethyl)amino]acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-α-(2-chlorophenyl)-α-[(diphenylmethyl)amino]acetonitrile(225918-54-7)
• EPA Substance Registry System: (S)-α-(2-chlorophenyl)-α-[(diphenylmethyl)amino]acetonitrile(225918-54-7)

Safety Data

• Hazardous Substances Data: 225918-54-7(Hazardous Substances Data)

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 89-98-5 2-chloro-benzaldehyde 
• 91-00-9 Benzhydrylamine 
• 69790-43-8 N-(2-chlorobenzylidene)-1,1-diphenylmethanamine 
• 387845-99-0 N-benzyhydryl-(2-chlorobenzylidene)-amine 

Downstream Products

• 225918-58-1 (2S)-2-(2-chlorophenyl)glycine hydrochloride 
• 225918-60-5 N-Boc-(S)-2-chlorophenylglycine 
• 141315-50-6 (S)-2-amino-(2-chlorophenyl)ethanoic acid 

Relevant articles and documents

Oxazoline-based organocatalyst for enantioselective strecker reactions: A protocol for the synthesis of levamisole

A chiral oxazoline-based or-ganocatalyst has been found to efficiently catalyze asymmetric Strecker reactions of various aromatic and aliphatic N-benzhydrylimines with trime-thylsilyl cyanide (TMSCN) as a cyanide source at -20°C to give α-aminoni-triles in high yield (96%) with excellent chiral induction (up to 98% ee). DFT calculations have been performed to rationalize the enantioselective formation of the product with the organo-catalyst in these reactions. The organo-catalyst has been characterized by single-crystal X-ray diffraction analysis, as well as by other analytical methods. This protocol has been extended to the synthesis of the pharmaceutically important drug molecule levamisole in high yield and with high enantioselectivity.

Self-assembled organic-inorganic hybrid silica with ionic liquid framework: A novel support for the catalytic enantioselective Strecker reaction of imines using Yb(OTf)3-pybox catalyst

Yb(OTf)3-pybox is immobilized in a novel self-assembled ionic liquid hybrid silica and has been successfully applied as a catalyst for the asymmetric Strecker hydrocyanation of aldimines. This catalytic system can be reused for at least 6 times without any significant loss of activity and enantioselectivity.

Highly enantioselective titanium-catalyzed cyanation of imines at room temperature

(Figure presented) A highly active and enantioselective titanium-catalyzed cyanatlon of imines at room temperature Is described. The catalyst used Is a partially hydrolyzed titanium alkoxide (PHTA) precatalyst together with a readily available N-salicyl-β-aminoalcohol ligand. Up to 98% ee was obtained with quantitative yields In 15 min of reaction time using 5 mol % of the catalyst. Various N-protecting groups such as benzyl, benzhydryl, Boc, and PMP are tolerated.