90390-13-9

Basic information

• Product Name: N-[4-(trifluoromethyl)benzyl]propan-1-amine
• Synonyms: Benzenemethanamine, N-propyl-4-(trifluoromethyl)-
• CAS NO: 90390-13-9
• Molecular Formula: C₁₁H₁₄F₃N
• Molecular Weight: 217.2308
• Mol File: 90390-13-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 228.6°C at 760 mmHg
• Flash Point: 92°C
• Density: 1.099g/cm³
• Vapor Pressure: 0.0729mmHg at 25°C
• Refractive Index: 1.455
• CAS DataBase Reference: N-[4-(trifluoromethyl)benzyl]propan-1-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-[4-(trifluoromethyl)benzyl]propan-1-amine(90390-13-9)
• EPA Substance Registry System: N-[4-(trifluoromethyl)benzyl]propan-1-amine(90390-13-9)

Safety Data

• Hazardous Substances Data: 90390-13-9(Hazardous Substances Data)

Upstream product

• 455-19-6 4-Trifluoromethylbenzaldehyde 

Downstream Products

• 1508310-57-3 N-[(4-nitrophenyl)methyl]-N-{[4-(trifluoromethyl)phenyl]methyl}-1-propanamine 
• 1508310-38-0 2-[4-(ethylsulfonyl)phenyl]-N-{4-[(propyl{[4-(trifluoromethyl)phenyl]methyl}amino)methyl]phenyl}acetamide 
• 1508310-58-4 [(4-aminophenyl)methyl]propyl{[4-(trifluoromethyl)phenyl]methyl}amine 

Relevant articles and documents

Methyl-triflate-mediated dearylmethylation of: N -(arylmethyl)carboxamides via the retro-Mannich reaction induced by electrophilic dearomatization/rearomatization in an aqueous medium at room temperature

We have developed a protocol for the dearylmethylation of N-(arylmethyl)carboxamides under metal-free conditions in an aqueous medium at room temperature. This protocol involves methyl triflate-mediated successive C-C and C-N bond cleavages (retro-Mannich reaction) induced by electrophilic dearomatization/rearomatization. The dearomatization/rearomatization strategy can be expected to inspire the development of novel transformations based on the C-C bond cleavage in an environmentally benign manner.

Pd(OAc)2-catalyzed carbonylation of amines

A phosphine-free catalytic system [Pd(OAc)2-Cu(OAc) 2-air] induced a substrate-specific carbonylation of amines in boiling toluene under CO gas (1 atm). Symmetrical N,N′-dialkylureas were obtained by the carbonylation of primary amines. N,N,N′-Trialkylureas were selectively formed by addition of a secondary amine to the above reaction vessel. Secondary amines did not give tetraalkylureas. However, dialkylamines with a phenyl group on their alkyl chains, such as N-monoalkylated benzylic amine or phenethylamine derivatives, underwent a direct aromatic carbonylation to afford five- or six-membered benzolactams. In the carbonylation, the chelation effect or steric repulsion between Pd(II) and the meta-substituent in the ortho-palladation and the ring sizes of cyclopalladation products that were formed prior to carbonylation were found to generate good site selectivity and increase the reaction rate. In contrast, carbonylation of ω- arylalkylamines with a hydroxyl group gave neither ureas nor benzolactams but instead produced 1,3-oxazolidinones smoothly. Hydrochlorides of amines also underwent carbonylation to afford the corresponding amides under the conditions used. This procedure made it possible to prepare ureas of amino acid esters and N-alkylcarbamates in practical yields.