5350-55-0

Basic information

• Product Name: N,N-dimethyl-1-(2-methylphenyl)-1-phenylmethanamine
• CAS NO: 5350-55-0
• Molecular Formula: C₁₆H₁₉N
• Molecular Weight: 225.3288
• Mol File: 5350-55-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 295.8°C at 760 mmHg
• Flash Point: 121.1°C
• Density: 0.996g/cm³
• Vapor Pressure: 0.00149mmHg at 25°C
• Refractive Index: 1.562
• CAS DataBase Reference: N,N-dimethyl-1-(2-methylphenyl)-1-phenylmethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-dimethyl-1-(2-methylphenyl)-1-phenylmethanamine(5350-55-0)
• EPA Substance Registry System: N,N-dimethyl-1-(2-methylphenyl)-1-phenylmethanamine(5350-55-0)

Safety Data

• Hazardous Substances Data: 5350-55-0(Hazardous Substances Data)

Upstream product

• 932-31-0 ortho-tolylmagnesium bromide 
• 827-36-1 2-(N,N-dimethylamino)-2-phenylacetonitrile 
• 100-94-7 dimethyldibenzylammonium chloride 
• 41870-52-4 α-phenyl-o-methylbenzyl chloride 
• 124-40-3 dimethyl amine 
• 16536-62-2 N-benzyl-N,N-dimethylphenylmethylammonium bromide 
• 103-83-3 N,N'-dimethylbenzylamine 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 68-12-2 N,N-dimethyl-formamide 
• 6639-19-6 N,N,2-trimethylbenzamide 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 102559-28-4 dimethyl-(2-methyl-benzhydryl)-amine oxide 

Relevant articles and documents

Transition-Metal-Free Reductive Functionalization of Tertiary Carboxamides and Lactams for α-Branched Amine Synthesis

A new method for the synthesis of α-branched amines by reductive functionalization of tertiary carboxamides and lactams is described. The process relies on the efficient and controlled reduction of tertiary amides by a sodium hydride/sodium iodide composite, in situ treatment of the resulting anionic hemiaminal with trimethylsilyl chloride and subsequent coupling with nucleophilic reagents including Grignard reagents and tetrabutylammonium cyanide. The new method exhibits broad functional-group compatibility, operates under transition-metal-free reaction conditions, and is suitable for various synthetic applications on both sub-millimole and on multigram scales.

Application of 13C NMR Spectroscopy and 13C-Labeled Benzylammonium Salts to the Study of Rearrangements of Ammonium Benzylides

Ylides generated from N-(cyanomethyl)-N,N-dimethyl-N-[α-(trimethylsilyl)benzyl]ammonium chloride (4) and fluoride anion afford the products of [1,2] shift 11 and [2,3] shift 13. Formation of product 13 shows that, in the presence of water from TBAF, rearrangements and [1,3]H shift in ylide intermediates become competitive processes. The reaction of N-benzyl-N,N-dimethyl-N-[α-(trimethylsilyl)benzyl]ammonium bromide (5) and 13C labeled (at the benzyl carbon) salt 5* gave a mixture of 10, 14, and 15 as products of [1,4], [1,2], and [2,3] rearrangement, respectively. 13C NMR spectra of products derived from salt 5* exclude [1,3]H shift in ylide 9a+-. Rearrangement of ylides generated from N-benzyl-N,N-dimethyl-N-[(dimethylphenylsilyl)methyl]ammonium bromide (6*) (enriched in 13C at benzyl carbon) and n-BuLi reveals that N,N-dimethyl-2-[(dimeth-ylphenylsilyl)methyl]benzylamine (20*) is not formed by a [1,4] shift but instead, via a [2,3] shift in silylmethylide followed by subsequent [1,4]Si and [1,2]H shift, as previously suggested in the literature. This mechanism is unique to some silyl-substituted ylides.