54220-19-8

Basic information

• Product Name: Benzenemethanamine, N-[(4-methylphenyl)methylene]-a-phenyl-
• CAS NO: 54220-19-8
• Molecular Formula: C21H19N
• Molecular Weight: 285.389
• Mol File: 54220-19-8.mol

Chemical Properties

• CAS DataBase Reference: Benzenemethanamine, N-[(4-methylphenyl)methylene]-a-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanamine, N-[(4-methylphenyl)methylene]-a-phenyl-(54220-19-8)
• EPA Substance Registry System: Benzenemethanamine, N-[(4-methylphenyl)methylene]-a-phenyl-(54220-19-8)

Safety Data

• Hazardous Substances Data: 54220-19-8(Hazardous Substances Data)

Upstream product

• 91-00-9 Benzhydrylamine 
• 10254-13-4 N-(Diphenylmethylen)-p-toloylsaeureamid 
• 99-94-5 p-Toluic acid 
• 104-87-0 4-methyl-benzaldehyde 

Downstream Products

• 1067616-66-3 N-benzhydryl-α-p-tolylglycine nitrile 
• 112254-36-1 Benzoic acid (E)-2-(benzhydrylidene-amino)-1-phenyl-2-p-tolyl-vinyl ester 
• 137321-01-8 methyl 2-((diphenylmethylene)amino)-2-(p-tolyl)acetate 
• 855419-61-3 (2R,3R)-ethyl 1-benzhydryl-3-p-tolylaziridine-2-carboxylate 
• 1036969-60-4 (2S,3S)-ethyl 1-benzhydryl-3-p-tolylaziridine-2-carboxylate 
• 144632-36-0 6-cyano-1,1-diphenyl-3-(p-toluoyl)-1H-isoindole 
• 144632-34-8 7-cyano-1,1-diphenyl-3-(p-tolyl)isoquinolin-4(1H)-one 
• 144632-32-6 4-(p-cyanobenzoyloxy)-4-(p-cyanophenyl)-1,1-diphenyl-3-(p-methylphenyl)-2-azabuta-1,3-diene 

Relevant articles and documents

Enantioselective Reductive Cyanation and Phosphonylation of Secondary Amides by Iridium and Chiral Thiourea Sequential Catalysis

The combination of transition-metal catalysis and organocatalysis increasingly offers chemists opportunities to realize diverse unprecedented chemical transformations. By combining iridium with chiral thiourea catalysis, direct enantioselective reductive cyanation and phosphonylation of secondary amides have been accomplished for the first time for the synthesis of enantioenriched chiral α-aminonitriles and α-aminophosphonates. The protocol is highly efficient and enantioselective, providing a novel route to the synthesis of optically active α-functionalized amines from the simple, readily available feedstocks. In addition, the reactions are scalable and the thiourea catalyst can be recycled and reused.

Asymmetric Strecker Reaction Arising from the Molecular Orientation of an Achiral Imine at the Single-Crystal Face: Enantioenriched l- and d-Amino Acids

Strecker synthesis has long been considered one of the prebiotic reactions for the synthesis of α-amino acids. However, the correlation between the origin of chirality and highly enantioenriched α-amino acids through this method remains a puzzle. In the r

Access to α-Arylglycines by Umpolung Carboxylation of Aromatic Imines with Carbon Dioxide

A straightforward and transition-metal-free approach for the efficient synthesis of α-arylglycine derivatives from aromatic imines and carbon dioxide was enabled by an umpolung carboxylation reaction. Various substituted diphenylmethimines underwent the carboxylation smoothly with carbon dioxide in the presence of potassium tert-butoxide and 18-crown-6 to give the corresponding carboxylated products in good to high yields. Besides the enhancement of the solubility of potassium tert-butoxide in THF, 18-crown-6 also plays key roles in suppressing the reverse protonation or 1, 3-proton shift isomerization as well as by stabilizing the carboxylated intermediate.

Replication of α-amino acids: Via Strecker synthesis with amplification and multiplication of chiral intermediate aminonitriles

Replication of chiral l- and d-α-(p-tolyl)glycine has been achieved in combination with the asymmetric induction, amplification and multiplication of their own chiral intermediates, l- and d-aminonitriles, in the solid-phase via the Strecker reaction between three achiral components, which is a plausible prebiotic mechanism for amino acid synthesis.

COMPOUNDS AND RELATED METHODS OF USE

Described herein are compounds of formula (I), related compositions, and their use, for example in the formation of α-amino acids or a precursor thereof such as an α-aminonitrile.

Self-supported chiral titanium cluster (SCTC) as a robust catalyst for the asymmetric cyanation of imines under batch and continuous flow at room temperature

A robust heterogeneous self-supported chiral titanium cluster (SCTC) catalyst and its application in the enantioselective imine-cyanation/Strecker reaction is described under batch and continuous processes. One of the major hurdles in the asymmetric Strecker reaction is the lack of availability of efficient and reusable heterogeneous catalysts that work at room temperature. We exploited the readily hydrolyzable nature of titanium alkoxide to synthesize a self-supported chiral titanium cluster (SCTC) catalyst by the controlled hydrolysis of a preformed chiral titanium-alkoxide complex. The isolated SCTC catalysts were remarkably stable and showed up to 98% enantioselectivity (ee) with complete conversion of the imine within 2 h for a wide variety of imines at room temperature. The heterogeneous catalysts were recyclable more than 10 times without any loss in activity or selectivity. The robustness, high performance, and recyclability of the catalyst enabled it to be used in a packed-bed reactor to carry out the cyanation under continuous flow. Up to 97% ee and quantitative conversion with a throughput of 45 mgh-1 were achieved under optimized flow conditions at room temperature in the case of benzhydryl imine. Furthermore, a three-component Strecker reaction was performed under continuous flow by using the corresponding aldehydes and amines instead of the preformed imines. A good product distribution was obtained for the formation of amino nitriles with ee values of up to 98%. Synthetically useful ee values were also obtained for challenging α-branched aliphatic aldehyde by using the three-component continuous Strecker reaction.

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.

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.

Catalytic asymmetric Strecker hydrocyanation of imines using Yb(OTf) 3-pybox catalysts

We have explored the highly enantioselective Strecker hydrocyanation of a wide range of aromatic, α,β-unsaturated, heterocyclic, and aliphatic aldimines with good to excellent conversions and ees up to 98% in the presence of catalytic amounts of Yb(OTf)s

Catalytic asymmetric aziridination with borate catalysts derived from VANOL and VAPOL ligands: Scope and mechanistic studies

An extended study of the scope and mechanism of the catalytic asymmetric aziridination of imines with ethyl diazoacetate mediated by catalysts prepared from the VANOL and VAPOL ligands and triphenylborate is described. Nonlinear studies with scalemic VANOL and VAPOL reveal an essentially linear relationship between the optical purity of the ligand and the product suggesting that the catalyst incorporates a single molecule of the ligand. Two species are present in the catalyst prepared from B(OPh)3 and either VANOL or VAPOL as revealed by 1H NMR studies. Mass spectral analysis of the catalyst mixture suggests that one of the species involves one ligand molecule and one boron atom (B1) and the other involves one ligand and two boron atoms (B2). The latter can be formulated as either a linear or cyclic pyroborate and the 11B NMR spectrum is most consistent with the linear pyroborate structure. Several new protocols for catalyst preparation are developed which allow for the generation of mixtures of the B1 and B2 catalysts in ratios that range from 10:1 to 1:20. Studies with catalysts enriched in the B1 and B2 species reveal that the B2 catalyst is the active catalyst in the VAPOL catalyzed asymmetric aziridination reaction giving significantly higher asymmetric inductions and rates than the B1 catalyst. The difference is not as pronounced in the VANOL series. A series of 12 different imines were surveyed with the optimal catalyst preparation procedure with the finding that the asymmetric inductions are in the low to mid 90s for aromatic imines and in the mid 80s to low 90s for aliphatic imines for both VANOL and VAPOL catalysts. Nonetheless, the crystallinity of the N-benzhydryl aziridines is such that nearly all of the 12 aziridine products screened can be brought to >99% ee with a single recrystallization.