10479-25-1

Basic information

• Product Name: N-ethyldibenzylamine
• Synonyms: N-ethyldibenzylamine;Dibenzylethylamine;Ethyldibenzylamine;N,N-Dibenzylethaneamine;N-Ethyl-N-(phenylmethyl)benzenemethanamine;N-Ethyl-N,N-dibenzylamine;Einecs 233-976-3
• CAS NO: 10479-25-1
• Molecular Formula: C₁₆H₁₉N
• Molecular Weight: 225.32876
• EINECS: 233-976-3
• Mol File: 10479-25-1.mol
• Article Data: 35

Chemical Properties

• Melting Point: 93-94 °C
• Boiling Point: 305.8°C at 760 mmHg
• Flash Point: 126.5°C
• Appearance: /
• Density: 1.009g/cm³
• Vapor Pressure: 0.000805mmHg at 25°C
• Refractive Index: 1.57
• PKA: 7.93±0.50(Predicted)
• CAS DataBase Reference: N-ethyldibenzylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-ethyldibenzylamine(10479-25-1)
• EPA Substance Registry System: N-ethyldibenzylamine(10479-25-1)

Safety Data

• Hazardous Substances Data: 10479-25-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthesis, p. 766, 1978 DOI: 10.1055/s-1978-24885

InChI:InChI=1/C16H19N/c1-2-17(13-15-9-5-3-6-10-15)14-16-11-7-4-8-12-16/h3-12H,2,13-14H2,1H3

Upstream product

• 100-44-7 benzyl chloride 
• 75-04-7 ethylamine 
• 10479-30-8 N,N-dibenzylacetamide 
• 64-17-5 ethanol 
• 52742-32-2 N,N-dibenzyl-O-benzoylhydroxylamine 
• 557-20-0 diethylzinc 
• 588-46-5 N-(phenylmethyl)acetamide 
• 100-46-9 benzylamine 
• 100-39-0 benzyl bromide 
• 14321-27-8 N-ethylbenzylamine 
• 100-52-7 benzaldehyde 
• 25576-20-9 N,N-dibenzylmethanethioamide 
• 677-22-5 tert-butylmagnesium chloride 
• 917-54-4 methyllithium 

Downstream Products

• 4217-54-3 9,10-dihydro-10-methylacridine 
• 719-54-0 10-methyl-9, 10-dihydro-9-acridinone 
• 20689-96-7 N-benzyl-N-ethylnitrous amide 
• 5336-53-8 dibenzylnitrosamine 
• 103398-03-4 N,N'-diethyl-N,N'-dibenzyl-bibenzyl-α,α'-diyldiamine 

Relevant articles and documents

WCl6/LiAlH4 PROMOTED TRANSFORMATION OF IMINES INTO SECONDARY AND TERTIARY AMINES

The reaction of WCl6/LiAlH4 with imines, R'N=CHR, gave tertiary amines, R'N(CH2R)2, and secondary amines, R'NHCHRCH2R.Isotope labeling experiments revealed that the reaction involved two types of azatungstenacyclobutanes, , produced from the reaction of an alkylidene tungsten intermediate with the imine C=N double bond.Formation of these metallacyclobutanes is highly dependent on the solvent used.

Reduction of antides to amines via catalytic hydrosilylation by a rhodium complex

Reduction of a wide range of tertiary amides with 2 molar equivalents of diphenylsilane was promoted by 0.1 mol% of RhH(CO)(PPh3)3 at room temperature, affording the corresponding tertiary amines in high yields. The synthetic utility is demonstrated by chemoselective reductions of amides having functional groups such as ester and epoxy groups which are not tolerated by the conventional reductions with LiAlH4 and BH3.

Cp*Ir complex bearing a flexible bridging and functional 2,2′-methylenebibenzimidazole ligand as an auto-tandem catalyst for the synthesis of N-methyl tertiary amines from imines via transfer hydrogenation/N-methylation with methanol

A Cp*Ir complex bearing a flexible bridging and functional 2,2′-methylenebibenzimidazole ligand was designed, synthesized, and found to be a general and efficient auto-tandem catalyst for the synthesis of N-methyl tertiary amines from imines via transfer hydrogenation/N-methylation with methanol as both hydrogen source and methylating reagent. In the presence of [Cp*Ir(2,2′-CH2BiBzImH2)Cl][Cl], a range of desirable products were obtained in high yields with nearly complete selectivities. The reaction is highly attractive due to the highly atom economy, and minimal consumption of chemicals and energy. Notably, this research exhibits new potential of metal–ligand bifunctional catalysts for the activation of methanol as C1 source for organic synthesis.

Manganese(III) Porphyrin-Catalyzed Dehydrogenation of Alcohols to form Imines, Tertiary Amines and Quinolines

Manganese(III) porphyrin chloride complexes have been developed for the first time as catalysts for the acceptorless dehydrogenative coupling of alcohols and amines. The reaction has been applied to the direct synthesis of imines, tertiary amines and quinolines where only hydrogen gas and/or water are formed as the by-product(s). The mechanism is believed to involve the formation of a manganese(III) alkoxide complex which degrades into the aldehyde and a manganese(III) hydride species. The latter reacts with the alcohol to form hydrogen gas and thereby regenerates the alkoxide complex.