13519-67-0

Basic information

• Product Name: N-(4-CHLOROPHENYL)-N-ETHYLFORMAMIDE
• Synonyms: N-ETHYL-P-CHLOROFORMANILIDE;N-(4-CHLOROPHENYL)-N-ETHYLFORMAMIDE;4-CHLORO-N-ETHYL-N-FORMYLANILINE
• CAS NO: 13519-67-0
• Molecular Formula: C₉H₁₀ClNO
• Molecular Weight: 183.63
• Mol File: 13519-67-0.mol

Chemical Properties

• Boiling Point: 310.2°Cat760mmHg
• Flash Point: 141.4°C
• Appearance: /
• Density: 1.198g/cm³
• Vapor Pressure: 0.000611mmHg at 25°C
• Refractive Index: 1.57
• CAS DataBase Reference: N-(4-CHLOROPHENYL)-N-ETHYLFORMAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-CHLOROPHENYL)-N-ETHYLFORMAMIDE(13519-67-0)
• EPA Substance Registry System: N-(4-CHLOROPHENYL)-N-ETHYLFORMAMIDE(13519-67-0)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 13519-67-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-(4-Chlorophenyl)-N-ethylformamide is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs and medications.
Used in Agrochemical Industry:
N-(4-Chlorophenyl)-N-ethylformamide is used as an intermediate in the synthesis of agrochemicals to aid in the creation of pesticides and other agricultural products.
Used in Organic Compound Production:
N-(4-Chlorophenyl)-N-ethylformamide is used as a building block in the production of various organic compounds, contributing to the synthesis of a wide range of chemical products.

InChI:InChI=1/C9H10ClNO/c1-2-11(7-12)9-5-3-8(10)4-6-9/h3-7H,2H2,1H3

Upstream product

• 106-47-8 4-chloro-aniline 
• 539-03-7 N-(4-chlorophenyl)acetamide 
• 64-18-6 formic acid 
• 13519-75-0 N-ethyl-4-chloro-aniline 

Downstream Products

• 257946-77-3 N-cyclopropyl-N-ethyl-p-chloroaniline 
• 35517-81-8 N-(4-Chloro-phenyl)-N-ethyl-thioformamide 
• 13519-75-0 N-ethyl-4-chloro-aniline 

Relevant articles and documents

A mechanistic comparison between cytochrome P450- and chloroperoxidase-catalyzed N-dealkylation of N,N-dialkyl anilines

Most peroxidases use histidine as an axial ligand for heme, while chloroperoxidase (CPO) uses a thiolate, which is similar to the ligand employed by cytochrome P450 (P450). Several studies have also shown that, unlike other peroxidases, CPO is capable of carrying out monooxygenation reactions in a similar manner to P450 in addition to typical peroxidase-like reactions. These observations have been attributed to the similarities of the active-site architecture of the two enzymes. Both enzymes have been shown to efficiently catalyze the oxidative N-dealkylation of amines. The similar magnitudes of the kinetic isotope effects determined for P 450- and CPO-catalyzed N-dealkylation of N,N-dimethylaniline have been used to propose that these reactions proceed through similar mechanisms. In this study, we have examined the mechanism of CPO-catalyzed N-dealkylation using a series of radical probes, 4-chloro-N-cyclopropyl-N-alkylanilines 1-3, which we have recently used in the mechanistic studies of P450, and compared the results with those of P450-catalyzed reactions. The results show that P450- and CPO-catalyzed reactions proceed through distinctly different mechanisms. As previously reported, while P 450-catalyzed reactions appear to proceed through a C α-hydrogen abstraction mechanism, CPO-catalyzed reactions proceed through a single electron/proton transfer (SET/H+) mechanism, similar to reactions catalyzed by Horseradish peroxidase (HRP). Thus, CPO may not be a good mechanistic model for P450-catalyzed N-dealkylations. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

P450/NADPH/O2- and P450/PhlO-catalyzed N-dealkylations are mechanistically distinct

A high-valent iron-oxo species analogous to the compound I of peroxidases has been thought to be the activated oxygen species in P450-catalyzed reactions. Spectroscopic characterization of the catalytically competent iron-oxo species in iodosobenzene (PhIO)-supported model reactions and parallels between these model reactions and PhIO- and NADPH/O2-supported P450 reactions have been taken as strong evidence for this proposal. To support this proposal, subtle differences observed in regio- and chemoselectivities, isotope effects, and source of oxygen, etc., between NADPH/O2- and PhIO-supported P450 reactions have been generally attributed to reasons other than the mechanistic differences between the two systems. In the present study, we have used a series of sensitive mechanistic probes, 4-chloro-N-cyclopropyl-N-alkylanilines, to compare and contrast the chemistries of the NADPH/O2- and PhIO-supported purified CYP2B1 N-dealkylation reactions. Herein we present the first experimental evidence to demonstrate that the NADPH/O2- and PhIO-supported P450 N-dealkylations are mechanistically distinct and, thus, the P450/PhIO system may not be a good mechanistic model for P450/NADPH/O2-catalyzed N-dealkylations. Copyright

N,N-DISUBSTITUTED LITHIUM BIS(CARBAMOYL)CUPRATE. A CONVENIENT COMPLEX FOR ONE-POT CONVERSIONS OF AMINES TO FORMAMIDES, OXAMIDES, CARBAMATES, AND OXAMIC ACIDS

Lithium bis(carbamoyl)cuprates (2) were readily derived from secondary amines such as N-methylaniline, N-methylbenzylamine, and diethylamine, under mild carbonylation conditions (0 deg C, 1 atm of carbon monoxide), but diphenylamine and benzylphenylamine were unsuitable as the starting materials.The carbamoylcopper complexes 2 formed in ether were readily converted to the corresponding formamides, oxamides, carbamates, and oxamic acids by the appropriate treatment.The formation and stability of 2 depended much on the solvent used.The higher polarity effect of the solvent (DME, THF, and HMPA) made 2 less stable and caused concomitant evolution of carbon monoxide in further reactions.A palladium catalyst was found to be effective for cross-coupling reactions of 2 with iodobenzene or (E)-β-bromostyrene.