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 
• 20914-19-6 phenyl-propyl-carbamonitrile 
• 106-94-5 propyl bromide 
• 62-53-3 aniline 
• 123-38-6 propionaldehyde 
• 1072-85-1 o-fluorobromobenzene 
• 5666-19-3 allyl-dipropyl-amine 
• 31004-44-1 propionic acid-(N,N'-diphenyl-hydrazide) 
• 589-09-3 N-allyl-N-phenylamine 
• 201230-82-2 carbon monoxide 
• 3334-89-2 1-Phenylazetidine 
• 763-29-1 2-Methyl-1-pentene 
• 622-37-7 Phenyl azide 

Downstream Products

• 180840-30-6 N-propyl-N-isopropylaniline 
• 13395-54-5 N-methyl-N-n-propylaniline 
• 19219-49-9 bis-(4-propylamino-phenyl)-methane 
• 19788-34-2 N-nitroso-N-n-propylaniline 
• 2696-84-6 4-propylaniline 
• 81090-35-9 N-(4-bromophenyl)-N-propylamine 
• 81090-47-3 2,4-dibromo-N-propyl-aniline 
• 2437-98-1 N-propyl-acetanilide 
• 78114-05-3 N,N'-diphenyl-N-propyl-thiourea 
• 2217-07-4 N,N-dipropylaniline 
• 2567-52-4 Chloressigsaeure-N.N-isopropylanilid 
• 30650-19-2 N-benzoyl-N'-phenyl-N'-propyl-thiourea 
• 37877-46-6 N-propyl-toluene-4-sulfonanilide 
• 56616-13-8 C₂₇H₃₆N₃P 

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.

Catalyst-free photoinduced selective oxidative C(sp3)-C(sp3) bond cleavage in arylamines

Due to the directional nature of sp3-hybridized orbitals and the absence of π-orbitals, the oxidative cleavage of the kinetically and thermodynamically stable C(sp3)-C(sp3) bond is extremely difficult and remains scarcely explored. In this work, under the double argument of quantum mechanics (QM) computations and meticulous experiments on our well-designed C-C single bond cleavage mechanism, we discovered a means of photoinduced selective oxidative C(sp3)-C(sp3) bond cleavage in arylamines, easily achieved by simple visible light irradiation using O2as a benign oxidant under very mild conditions. The utility of our methodology was demonstrated by the C(sp3)-C(sp3) bond cleavage in morpholine/piperazine arylamines with excellent functional group tolerance. Importantly, our methodology is noteworthy, not only in that it does not require any catalysts, but also in that it provides valuable possibilities for the scalable functionalization of clinical drugs and natural products.

C–N Cross-coupling Reactions of Amines with Aryl Halides Using Amide-Based Pincer Nickel(II) Catalyst

Abstract: An approach to C–N cross-coupling reactions of aryl halides with amines in the presence of an amide-based pincer nickel(II) catalyst (2) is described. For 3?h reactions at 110?°C with 0.2?mol% catalyst, aryl bromides gave higher turnover numbers (TON) than the corresponding chlorides or iodides. Both primary and secondary amines could be used with the former giving higher TON. However, sterically hindered amines showed lower TON. In elucidating the mechanism of this nickel complex-catalyzed C–N cross coupling reaction it was found that the rate of reaction was unchanged in the presence of radical quenchers and a plausible Ni(I)–Ni(III) pathway is proposed. Graphic Abstract: [Figure not available: see fulltext.]Nickel pincer catalyst proved to be excellent catalyst for the C-N cross-coupling reaction with the high turnover number (TON) for 1° and 2° amines and different nonactivated aryl halides under optimum conditions.