537-11-1

Basic information

• Product Name: N,N-dibenzyl-2-bromoethanamine
• CAS NO: 537-11-1
• Molecular Formula: C₁₆H₁₈BrN
• Molecular Weight: 304.2248
• Mol File: 537-11-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 355.9°C at 760 mmHg
• Flash Point: 169°C
• Density: 1.286g/cm³
• Vapor Pressure: 3.04E-05mmHg at 25°C
• Refractive Index: 1.601
• CAS DataBase Reference: N,N-dibenzyl-2-bromoethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-dibenzyl-2-bromoethanamine(537-11-1)
• EPA Substance Registry System: N,N-dibenzyl-2-bromoethanamine(537-11-1)

Safety Data

• Hazardous Substances Data: 537-11-1(Hazardous Substances Data)

Upstream product

• 74-96-4 ethyl bromide 
• 51-50-3 N,N-dibenzyl-2-chloroethanamine 
• 101-06-4 N,N-dibenzyl-2-aminoethanol 

Downstream Products

• 1010729-21-1 2-(N,N-dibenzylamino)ethylformate 
• 1259436-26-4 ethyl 4-[2-(dibenzylamino)ethyl]-2,7-dimethyl-6-{[(3R)-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-3-piperidinyl](2-propanyl)carbamoyl}-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate 
• 1259436-29-7 2-methyl-2-propanyl (3R)-3-[({4-[2-(dibenzylamino)ethyl]-2-(hydroxymethyl)-2,7-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl}carbonyl)(2-propanyl)amino]-1-piperidinecarboxylate 
• 1259436-28-6 4-[2-(dibenzylamino)ethyl]-2,7-dimethyl-6-{[(3R)-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-3-piperidinyl](2-propanyl)carbamoyl}-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid 
• 1259436-27-5 2-Methyl-2-propanyl (3R)-3-[({4-[2-(dibenzylamino)ethyl]2-(methoxymethyl)-2,7-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl}carbonyl)(2-propanyl)amino]-1-piperidinecarboxylate 
• 1262643-31-1 1-(2-dibenzylamino-ethyl)-1H-indole-3-carbaldehyde 
• 855308-12-2 Rh(5,10,15,20-tetratolylporphyrinato)(β-N,N-dibenzylaminoethyl) 
• 104738-97-8 (2S,5R)-2-tert-butyl-5-<2-(dibenzylamino)ethyl>-2,5-dihydro-3,6-dimethoxypyrazine 
• 104738-97-8 (2S,5S)-2-tert-butyl-5-<2-(dibenzylamino)ethyl>-2,5-dihydro-3,6-dimethoxypyrazine 
• 104738-97-8 (2R,5R)-2-tert-Butyl-5-<2-(dibenzylamino)ethyl>-2,5-dihydro-3,6-dimethoxypyrazine 
• 104738-97-8 (2R,5S)-2-tert-butyl-5-<2-(dibenzylamino)ethyl>-2,5-dihydro-3,6-dimethoxypyrazine 

Relevant articles and documents

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Formate ester synthesis via reaction of 2-bromoethylamines with dimethylformamide

2-Bromoethylamines are converted to the corresponding formate esters in the presence of DMF. Both primary and secondary bromides are smoothly transformed to the esters in satisfactory yields. The reaction mechanism involves the formation of an aziridinium ion, which upon reaction with DMF forms a Vilsmeier-type intermediate that is further hydrolyzed to the corresponding formates. Participation of the β-amino group appears to control not only the regioselectivity but also the stereoselectivity of the reaction. Application of the reaction conditions to chiral substrates indicated that non-rearranged products are formed with retention of configuration at the reacting center.