102904-41-6

Basic information

• Product Name: Benzonitrile, 4-[(E)-(phenylmethylene)amino]-
• CAS NO: 102904-41-6
• Molecular Formula: C14H10N2
• Molecular Weight: 206.247
• Mol File: 102904-41-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzonitrile, 4-[(E)-(phenylmethylene)amino]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4-[(E)-(phenylmethylene)amino]-(102904-41-6)
• EPA Substance Registry System: Benzonitrile, 4-[(E)-(phenylmethylene)amino]-(102904-41-6)

Safety Data

• Hazardous Substances Data: 102904-41-6(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 873-74-5 4-Aminobenzonitrile 
• 18523-41-6 4-azidobenzonitrile 
• 108-88-3 toluene 

Downstream Products

• 73013-72-6 2-phenyl-6-quinolinecarbonitrile 
• 138409-89-9 1,2,3,4-tetrahydro-2,4-diphenyl-6-quinolinecarbonitrile 

Relevant articles and documents

π-π Stacking versus steric effects in stereoselectivity control: Highly diastereoselective synthesis of syn-1,2-diarpropylamines

N-Arylarylideneamines react with sulfinylbenzyl carbanions derived from 2-(p-tolylsulfinyl)toluenes (S)-1 and (S)-2, affording epimeric mixtures at C1 of 1,2-diarylethyl- and 1,2-diarylpropylamine derivatives. The sulfinyl group completely controls the configuration at C2 in the reactions of (S)-2. The configuration at Cl depends on the electron density of the ring adjacent to the iminic carbon atom which is modulated by π-π stacking interactions with the ring joined to the carbanionic centre. The stereoselectivity was controlled by modifying the acceptor character of the arylideneamine ring with appropriate substituents, the formation of the highly selective (R) configuration at C1 being made possible by electron-donating groups. N-(2,4,6-Trimethoxyphenyl) arylideneamines have been shown to be suitable starting materials for the preparation of (R)-1,2-diarylethyl- and (1R,2S)-1,2-diarylpropylamines (syn epimers) in a highly stereoselective manner.

Amination of benzylic C-H bonds by arylazides catalyzed by CoII-porphyrin complexes: A synthetic and mechanistic study

CoII-porphyrin complexes catalyze the reaction of aromatic azides (ArN3) with hydrocarbons that contain a benzylic group (ArR1R2CH) to give the corresponding amines (ArR1R2C-HAr). When at least one of the R substituents is hydrogen, the catalytic reaction proceeds further to give the imine ArRC=NAr in good yields. The reaction mechanism has been investigated. The reaction proceeds through a reversible coordination of the arylazide to the ConII-porphyrin complex. This unstable adduct can either react with the hydrocarbon in the rate-determining step or decompose by a unimolecular mechanism to afford a putative nitrene complex, which reacts with more azide, but not with the hydrocarbon, to afford the byproduct diaryldiazene. The kinetics of the catalytic reaction have been investigated for a range of azides and substituted toluenes. Arvlazides with electron-withdrawing substituents react at a faster rate and a good correlation is found between the log(k) and the Taft parameters. On the other hand, an excellent correlation between the logarithm of the rate for substituted toluenes relative to that of toluene and a radical parameter (σJJ) alone was found, with no significant contribution by polar parameters. An explanation has been proposed for this anomalous effect and for the very high isotopic effect (kH/kD= 14) found.