940-36-3

Basic information

• Product Name: N-(4-Chlorophenyl)carbamic acid methyl ester
• Synonyms: (4-Chlorophenyl)carbamic acid methyl ester;4-Chlorophenylcarbamic acid methyl ester;N-(4-Chlorophenyl)carbamic acid methyl ester;p-Chlorocarbanilic acid methyl ester;methyl N-(4-chlorophenyl)carbamate
• CAS NO: 940-36-3
• Molecular Formula: C₈H₈ClNO₂
• Molecular Weight: 185.61
• Mol File: 940-36-3.mol

Chemical Properties

• Boiling Point: 220.9°C at 760 mmHg
• Flash Point: 87.4°C
• Appearance: /
• Density: 1.317g/cm³
• Vapor Pressure: 0.111mmHg at 25°C
• Refractive Index: 1.584
• CAS DataBase Reference: N-(4-Chlorophenyl)carbamic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-Chlorophenyl)carbamic acid methyl ester(940-36-3)
• EPA Substance Registry System: N-(4-Chlorophenyl)carbamic acid methyl ester(940-36-3)

Safety Data

• Hazardous Substances Data: 940-36-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H8ClNO2/c1-12-8(11)10-7-4-2-6(9)3-5-7/h2-5H,1H3,(H,10,11)

Upstream product

• 67-56-1 methanol 
• 104-12-1 p-chlorphenylisocyanate 
• 122-01-0 4-chloro-benzoyl chloride 
• 110-91-8 morpholine 
• 30645-78-4 3-(4-chloro-phenyl)-6-methyl-[1,3]oxazine-2,4-dione 
• 2877-13-6 N-(4-chlorophenyl)-2,2,2,-trichloroacetamide 
• 201230-82-2 carbon monoxide 
• 106-47-8 4-chloro-aniline 
• 124-41-4 sodium methylate 
• 100-00-5 4-chlorobenzonitrile 
• 619-56-7 4-chlorobenzamide 
• 616-38-6 carbonic acid dimethyl ester 
• 160852-85-7 2-[2-(2-methoxyethoxy)ethoxy]ethyl methyl carbonate 
• 5167-80-6 4-chlorophenyl carbamic acid 

Downstream Products

• 39073-68-2 Chloromethyl-(4-chloro-phenyl)-carbamic acid methyl ester 
• 106-47-8 4-chloro-aniline 
• 5006-92-8 1-(p-Chlor-phenyl)-3-n-octyl-harnstoff 
• 104-12-1 p-chlorphenylisocyanate 
• 539-03-7 N-(4-chlorophenyl)acetamide 
• 2759-54-8 N-(4-chlorophenyl)propionamide 
• 7017-09-6 N-(4-chloro-phenyl)-3-methyl-butyramide 
• 52625-27-1 N-(4-chlorophenyl)morpholine-4-carboxamide 
• 932-96-7 N-methyl(p-chloroaniline) 
• 60561-39-9 p-Chlorphenyl-N-methyl-carbamidsaeure-methylester 

Relevant articles and documents

METHOD FOR PRODUCING CARBAMATE

PROBLEM TO BE SOLVED: To provide a method that can produce carbamate with high yield and high selectivity, and excellent economical efficiency, using more different kinds of amines. SOLUTION: A method for producing carbamate has a reaction step where, in the presence of calcium carbide and potassium carbonate, a reaction is induced among amine, methanol, and carbon dioxide. The reaction step is preferably performed at a temperature of 165-180°C. The reaction step is preferably performed at a carbon dioxide pressure of 3-5 MPa. The reaction step is preferably performed using an acetonitrile solvent. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2021,JPOandINPIT

Copper-Catalyzed Coupling of Amines with Carbazates: An Approach to Carbamates

A new approach for the preparation of carbamatesviathe copper-catalyzed cross-coupling reaction of amines with alkoxycarbonyl radicals generated from carbazates is described. This environmentally friendly protocol takes place under mild conditions and is compatible with a wide range of amines, including aromatic/aliphatic and primary/secondary substrates.

Atomically Dispersed Copper on N-Doped Carbon Nanosheets for Electrocatalytic Synthesis of Carbamates from CO2 as a C1 Source

The synthesis of carbamates by electrocatalytic reduction of CO2 is an effective method to realize the utilization of CO2 resources. The development of high-performance electrocatalysts to complete this process more efficiently is of great significance to sustainable development. Owing to their unique structural characteristics, single-atom catalysts are expected to promote the reaction process more efficiently. In this study, an atomically dispersed Cu species on N-doped carbon nanosheet composite material (Cu?N?C) was prepared by metal-organic framework derivatization. Compared with traditional Cu bulk electrodes, the Cu?N?C material has better catalytic performance for the synthesis of methyl N-phenylcarbamate; and the optimized yield reached 71 % at room temperature and normal pressure. The Cu?N?C material has good stability that the catalytic performance does not decrease after repeated use for 10 times. In addition, the Cu?N?C material has good applicability to this catalytic system, and a variety of amines can be smoothly converted into corresponding carbamates.

N-Aryl and N-Alkyl Carbamates from 1 Atmosphere of CO2

We have successfully isolated and characterized the zinc carbamate complex (phen)Zn(OAc)(OC(=O)NHPh) (1; phen=1,10-phenanthroline), formed as an intermediate during the Zn(OAc)2/phen-catalyzed synthesis of organic carbamates from CO2, amines, and the reusable reactant Si(OMe)4. Density functional theory calculations revealed that the direct reaction of 1 with Si(OMe)4 proceeds via a five-coordinate silicon intermediate, forming organic carbamates. Based on these results, the catalytic system was improved by using Si(OMe)4 as the reaction solvent and additives like KOMe and KF, which promote the formation of the five-coordinated silicon species. This sustainable and effective method can be used to synthesize various N-aryl and N-alkyl carbamates, including industrially important polyurethane raw materials, starting from CO2 under atmospheric pressure.

Methoxycarbonylation of Alkyl-, Cycloalkyl-, and Arylamines with Dimethyl Carbonate in the Presence of Binder-Free Zeolite

Abstract: Methyl N-alkyl-, N-cycloalkyl-, and N-arylcarbamates were synthesized by reaction of the correspondingamines with dimethyl carbonate in the presence of binder-free FeHY zeolite. Theoptimal conditions (reactant ratio, amount of the catalyst, temperature,reaction time) were found to afford the target products with high yields.

PRODUCTION METHOD FOR AMIDATE COMPOUND

A method for producing an amidate compound represented by Formula (3), comprising reacting a urethane compound represented by Formula (1) with a carboxylate compound represented by Formula (2): (in the formulas, A, n, R1, R2, R3, R4, R5, R6, X, and a are as described in the Description).

Amidate compound, catalyst for polyurethane production, and method for producing polyurethane resin

Provided is an amidate compound represented by the formula (1): wherein A is a substituted or unsubstituted hydrocarbon group, n is an integer of 1 or more, and D is a nitrogen-containing organic group represented by the formula (2): wherein R1, R2, and R3 are the same or different, and are each a hydrocarbon group that may contain a heteroatom; some or all of R1, R2, and R3 may be bonded together to form a ring structure; X is a nitrogen atom, an oxygen atom, or a sulfur atom; and a is 0 or 1, wherein a is 1 when X is a nitrogen atom, and a is 0 when X is an oxygen atom or a sulfur atom.

Oxidative Photochlorination of Electron-Rich Arenes via in situ Bromination

Electron-rich arenes are oxidatively photochlorinated in the presence of catalytic amounts of bromide ions, visible light, and 4CzIPN as organic photoredox catalyst. The substrates are brominated in situ in a first photoredox-catalyzed oxidation step, followed by a photocatalyzed ipso-chlorination, yielding the target compounds in high ortho/para regioselectivity. Dioxygen serves as a green and convenient terminal oxidant. The use of aqueous hydrochloric acid as the chloride source reduces the amount of saline by-products.

Calcium carbide as a dehydrating agent for the synthesis of carbamates, glycerol carbonate, and cyclic carbonates from carbon dioxide

Carbon dioxide (CO2) is a nontoxic and inexpensive C1 building block, which can be used for the synthesis of valuable chemicals such as aromatic carbamates from anilines and methanol (MeOH), glycerol carbonate from glycerol, and cyclic carbonates from diols. However, these reactions generate water as the byproduct and suffer from thermodynamic limits, which lead to low yields. Calcium carbide (CaC2) is a renewable chemical, which can be recycled from calcium that is abundant in the Earth's crust. Furthermore, CaC2 rapidly reacts with water. In this work, we used CaC2 as a dehydrating agent for the direct synthesis of carbamates (including polyurethane precursors) from amines, CO2, and MeOH. All reagents were commercially available. In addition, CaC2 was employed for the synthesis of glycerol carbonate from glycerol and CO2 with a zinc catalyst and N-donor ligand. A similar protocol was applied to synthesize cyclic carbonates from diols and CO2.

Interaction of dimethyl carbonate with anilines in the presence of potassium methylate: Kinetics and the role of the base

The kinetic patterns of the reaction between dimethyl carbonate and anilines in the presence of a potassium methylate as a catalyst were studied. The mechanism of aminolysis was clarified, which includes the detachment of the proton from the amino group of aniline and the subsequent attack of the resulting anion on the carbonyl group of dimethyl carbonate. It is shown that when the reaction occurs in the dimethyl carbonate-methanol 3:1 system, the process can be described as an irreversible first-order reaction in the aniline though the target reaction is complicated by side interaction between potassium methylate and dimethyl carbonate. The rate constants of the target reaction with substituted anilines and of the side reaction in the temperature range of 70-90°C were determined. It is shown that the influence of the substituent on the reaction rate is described by the Hammett equation, with the constant of the reaction series being positive and the best correlation being achieved for ??-scale. The results obtained are consistent with the proposed mechanism of the reaction and are explained by the facilitation of the aniline deprotonation with increasing acceptor properties of the substituent. Effective activation energies for the reaction of various anilines with dimethyl carbonate are found.