34039-84-4

Basic information

• Product Name: Acetonitrile, [(phenylmethylene)amino]-
• CAS NO: 34039-84-4
• Molecular Formula: C9H8N2
• Molecular Weight: 144.176
• Mol File: 34039-84-4.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Acetonitrile, [(phenylmethylene)amino]-(CAS DataBase Reference)
• NIST Chemistry Reference: Acetonitrile, [(phenylmethylene)amino]-(34039-84-4)
• EPA Substance Registry System: Acetonitrile, [(phenylmethylene)amino]-(34039-84-4)

Safety Data

• Hazardous Substances Data: 34039-84-4(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 540-61-4 2-aminoacetonitrile 
• 6011-14-9 2-aminoacetonitrile hydrochloride 
• 151-63-3 aminoacetonitrile neutral sulfate 
• 100-39-0 benzyl bromide 
• 3010-05-7 benzylaminoacetonitrile 

Downstream Products

• 102845-50-1 (1R,3R,3aS,6aR)-5-Methyl-4,6-dioxo-3-phenyl-octahydro-pyrrolo[3,4-c]pyrrole-1-carbonitrile 
• 37525-10-3 5-benzylidenamino-3H-thiazole-2-thione 
• 140-29-4 phenylacetonitrile 
• 1582302-33-7 C₉H₇FN₂ 
• 100-52-7 benzaldehyde 
• 1582302-34-8 C₉H₇FN₂ 
• 1582302-35-9 C₉H₇N₃O₂ 
• 1582302-36-0 C₉H₇N₃O₂ 
• 1582302-37-1 C₇H₆N₂O 
• 1582302-38-2 C₇H₆N₂S 
• 22483-19-8 [2-Methyl-prop-(E)-ylideneamino]-acetonitrile 
• 1582302-29-1 C₈H₇N₃ 
• 1582302-30-4 C₉H₇ClN₂ 
• 95730-58-8 2-(4-chlorobenzylideneamino)acetonitrile 

Relevant articles and documents

Synthesis of β-prolinols via [3+2] cycloaddition and one-pot programmed reduction: Valuable building blocks for polyheterocycles

A novel two-step synthesis of multisubstituted β-prolinols has been developed, featuring a [3+2] cycloaddition of azomethine ylides and a programmed reduction triggered by the combination of borane and lithium aluminum hydride (LAH). β-Prolinols are shown to be valuable building blocks for polyheterocycles.

Silver-catalyzed dynamic systemic resolution of α-iminonitriles in a 1,3-dipolar cycloaddition process

A dynamic azomethine ylide system was established using Sc(OTf)3 and Ag/Taniaphos as catalysts. The system was subsequently kinetically resolved in a tandem 1,3-dipolar cycloaddition process where the silver complex acted as both a reaction catalyst and an external selector, resulting in the formation of an exclusive pyrrolidine product in good yield and enantiopurity. This journal is the Partner Organisations 2014.

The synthesis of alkyl aryl nitriles from N-(1-arylalkylidene)-cyanomethylamines. Part 2. Mechanism

The mechanism of the rearrangement of N-(1-arylalkylidene)cyanomethylamines ArC(=NCH2CN)R 1 to the corresponding nitriles ArCH(CN)R2 (in DMF, at 150°C, with K2CO3) is described. Reaction 1 → 2 was investigated for different types of imine 1, and it was found that with a leaving group other than CN- the reaction does not proceed to yield the nitrile, whereas imines such as PhC(=NCH2CN)H, prepared starting from aldehydes rather than ketones, yield the expected phenylacetonitrile even at temperatures as low as 120°C. Evidence for the mechanism comes from a study of the reactivity of the postulated intermediates: 2-cyano-3-phenylaziridine 4c, and 2,2-diphenyl-2H-azirine 5b. The route involving aziridine 4c is ruled out, since this compound does not react at all under the investigated conditions. The 2H-azirine 5b instead, yields the corresponding diphenylacetonitrile in DMF with K2CO3, at 150°C. The transformation seems to involve an initial deprotonation, followed by an intramolecular ring closure-CN elimination step, which yields the 2H-azirine. The azirine then isomerizes to the nitrile. Additional evidence for the intermediacy of the 2H-azirine, based on 1H NMR monitoring of the reaction 1 → 2, is described. Finally, the results of a simple isotope exchange experiment provide a rationale for the previously observed scrambling of labels, and further confirm the proposed mechanism.