622-80-0

Basic information

• Product Name: N-Propylaniline
• Synonyms: N-Propylbenzenamine;N-Propylbenzeneamine;N-Propylaniline;Aniline, N-n-propyl-;Aniline, N-propyl-;Benzenamine, N-propyl-;N-Phenyl-n-propylamine;n-propyl-benzenamin
• CAS NO: 622-80-0
• Molecular Formula: C₉H₁₃N
• Molecular Weight: 135.21
• EINECS: 210-754-4
• Mol File: 622-80-0.mol
• Article Data: 132

Chemical Properties

• Melting Point: -6.87°C (estimate)
• Boiling Point: 220°C
• Flash Point: 91°C
• Appearance: /
• Density: 0,95 g/cm3
• Vapor Pressure: 0.109mmHg at 25°C
• Refractive Index: 1.5410 to 1.5440
• PKA: 5.04±0.20(Predicted)
• CAS DataBase Reference: N-Propylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-Propylaniline(622-80-0)
• EPA Substance Registry System: N-Propylaniline(622-80-0)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 622-80-0(Hazardous Substances Data)

Usage

Preparation

N-propylaniline was efficiently synthesized in a vapor phase from aniline and 1-propanol at atmospheric pressure over the Cu/SiO2 catalyst that was prepared by the incipient wetness method and temperature-programmed calcination. The catalyst exhibited very high activity and selectivity. At the reaction temperature of 260°C, 1-propanol conversion reached 100%, and the selectivity for N-propylaniline exceeded 92%. The results of X-ray diffraction showed that the Cu/SiO2 catalyst with high catalytic activity and selectivity had good crystallinity of copper.https://doi.org/10.1016/S1872-2067(07)60027-8

InChI:InChI=1/C9H13N/c1-2-8-10-9-6-4-3-5-7-9/h3-7,10H,2,8H2,1H3

Upstream product

• 71-23-8 propan-1-ol 
• 142-04-1 aniline hydrochloride 
• 106-94-5 propyl bromide 
• 62-53-3 aniline 
• 123-38-6 propionaldehyde 
• 3334-89-2 1-Phenylazetidine 
• 763-29-1 2-Methyl-1-pentene 
• 622-37-7 Phenyl azide 
• 620-71-3 N-(phenyl)-2-methylacetamide 
• 118793-04-7 N-phenylpropan-1-imine 
• 3768-55-6 N-trimethylsilylaniline 
• 98-95-3 nitrobenzene 
• 71-36-3 butan-1-ol 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 180840-30-6 N-propyl-N-isopropylaniline 
• 54813-78-4 N-Propyl-N-ethylaniline 
• 13395-54-5 N-methyl-N-n-propylaniline 
• 19219-49-9 bis-(4-propylamino-phenyl)-methane 
• 2217-07-4 N,N-dipropylaniline 
• 2567-52-4 Chloressigsaeure-N.N-isopropylanilid 
• 30650-19-2 N-benzoyl-N'-phenyl-N'-propyl-thiourea 
• 38804-92-1 Butansulfonsaeure-N-propyl-anilid 
• 2437-98-1 N-propyl-acetanilide 
• 16885-94-2 1-propyl-1H-indole 
• 2696-84-6 4-propylaniline 

Relevant articles and documents

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BF3·Et2O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant

A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF3·Et2O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug molecules and biologically relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF3and hydride transfer from formic acid.

Cooperative catalysis of molybdenum with organocatalysts for distribution of products between amines and imines

Multi-amino groups and nitrogen donors compound was discovered as an organocatalyst for N-alkylation of alcohols with amines in the presence of Mo(CO)6. The Mo(CO)6/organocatalyst binary system has shown to be a highly active catalyst for the N-alkylation reaction between alcohols and amines with excellent tolerance of variable starting materials bearing different functional groups. Of particular note, this method possessing a superiority selectivity in the synthesis of N-alkylated amines or imines, which can be controlled by the reaction temperature. The cooperative catalysis mechanism in combination of Mo(CO)6 with organocatalyst was elucidated by control experiments.

Catalyst-Free Electrosynthesis of Benzimidazolones through Intramolecular Oxidative C?N Coupling

The electrochemical synthesis of N, N’-disubstituted benzimidazolones from ureas through an intramolecular anodic dehydrogenative N?H/C?H coupling has been developed. The reaction undergoes under the undivided electrolysis conditions and obviates the need for any catalysts and chemical oxidants. (Figure presented.).