5817-68-5

Basic information

• Product Name: methyl cyclohexylcarbamate
• Synonyms: Carbamic acid, cyclohexyl-, methyl ester; carbamic acid, N-cyclohexyl-, methyl ester
• CAS NO: 5817-68-5
• Molecular Formula: C₈H₁₅NO₂
• Molecular Weight: 157.2102
• Mol File: 5817-68-5.mol

Chemical Properties

• Boiling Point: 250.3°C at 760 mmHg
• Flash Point: 105.2°C
• Density: 1.01g/cm³
• Vapor Pressure: 0.0218mmHg at 25°C
• Refractive Index: 1.463
• CAS DataBase Reference: methyl cyclohexylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl cyclohexylcarbamate(5817-68-5)
• EPA Substance Registry System: methyl cyclohexylcarbamate(5817-68-5)

Safety Data

• Hazardous Substances Data: 5817-68-5(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 931-53-3 Cyclohexyl isocyanide 
• 3315-16-0 silver cyanate 
• 110-83-8 cyclohexene 
• 86298-22-8 1H-benzotriazole-1-carboxylic acid methyl ester 
• 108-91-8 cyclohexylamine 
• 616-38-6 carbonic acid dimethyl ester 
• 1122-56-1 cyclohexylcarboxamide 
• 2387-23-7 1,3-Dicyclohexylurea 
• 124-38-9 carbon dioxide 
• 54208-97-8 N-cyclohexyl carbonimidodithioic acid dimethyl ester 
• 20190-03-8 cyclohexylammonium N-cyclohexylcarbamate 
• 74-88-4 methyl iodide 
• 159493-47-7 Methyl 2-O-(Cyclohexylcarbamoyl)-3,4-O-(2,2,2-trichloroethylidene)-α-D-altropyranoside 

Downstream Products

• 933-40-4 cycloxexanone dimethyl ketal 
• 3173-53-3 Cyclohexyl isocyanate 
• 67-56-1 methanol 
• 108-91-8 cyclohexylamine 
• 17671-80-6 butyl N-cyclohexylcarbamate 
• 56475-90-2 Cyclohexyl-methoxymethyl-carbamic acid methyl ester 
• 807331-78-8 C₉H₁₆NO₂⁽¹⁺⁾ 
• 609769-60-0 N-cyclohexyl-N-(phenylethynyl)carbamic acid methyl ester 
• 25855-24-7 N-benzyl-N'-cyclohexylurea 
• 931-53-3 Cyclohexyl isocyanide 
• 119407-12-4 cyclohexyl(trimethylsilylmethyl)carbamic acid methyl ester 
• 91467-18-4 N-cyclohexyl-N-(methoxycarbonyl)oxamate 

Relevant articles and documents

Dehydrogenative Synthesis of Carbamates from Formamides and Alcohols Using a Pincer-Supported Iron Catalyst

We report that the pincer-ligated iron complex (iPrPNP)Fe(H)(CO) [1, iPrPNP- = N(CH2CH2PiPr2)2-] is an active catalyst for the dehydrogenative synthesis of N-alkyl- and N-aryl-substituted carbamates from formamides and alcohols. The reaction is compatible with industrially relevant N-alkyl formamides, as well as N-aryl formamides, and 1°, 2°, and benzylic alcohols. Mechanistic studies indicate that the first step in the reaction is the dehydrogenation of the formamide to a transient isocyanate by 1. The isocyanate then reacts with the alcohol to generate the carbamate. However, in a competing reaction, the isocyanate undergoes a reversible cycloaddition with 1 to generate an off-cycle species, which is the resting state in catalysis. Stoichiometric experiments indicate that high temperatures are required in catalysis to facilitate the release of the isocyanate from the cycloaddition product. We also identified several other off-cycle processes that occur in catalysis, such as the 1,2-addition of the formamide or alcohol substrate across the Fe-N bond of 1. It has already been demonstrated that the transient isocyanate generated from dehydrogenation of the formamide can be trapped with amines to form ureas and, in principle, the isocyanate could also be trapped with thiols to form thiocarbamates. Competition experiments indicate that trapping of the transient isocyanate with amines to produce ureas is faster than trapping with an alcohol to produce carbamates and thus ureas can be formed selectively in the presence of alcohols. In contrast, thiols bind irreversibly to the iron catalyst through 1,2 addition across the Fe-N bond of 1, and it is not possible to produce thiocarbamates. Overall, our mechanistic studies provide general guidelines for facilitating dehydrogenative coupling reactions using 1 and related catalysts.

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.

Ceria supported Ru0-Ruδ+ clusters as efficient catalyst for arenes hydrogenation

Selective hydrogenation of aromatic amines, especially chemicals such as aniline and bis(4-aminocyclohexyl)methane for non-yellowing polyurethane, is of particular interests due to the extensive applications. To conquer the existing difficulties in selective hydrogenation, the Ru0-Ruδ+/CeO2 catalyst with solid frustrated Lewis pairs was developed for aromatic amines hydrogenation with excellent activity and selectivity under relative milder conditions. The morphology, electronic and chemical properties, especially the Ru0-Ruδ+ clusters and reducible ceria were characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electronic microscopy (SEM), X-ray photoelectron spectroscopy (XPS), CO2 temperature programmed desorption (CO2-TPD), H2 temperature programmed reduction (H2-TPR), H2 diffuse reflectance Fourier transform infrared spectroscopy (H2-DRIFT), Raman, etc. The 2% Ru/CeO2 catalyst exhibited good conversion of 95% and selectivity greater than 99% toward cyclohexylamine. The volcano curve describing the activity and Ru state was found. Owning to the “acidic site isolation” by surrounding alkaline sites, condensation between the neighboring amine molecules could be effectively suppressed. The catalyst also showed good stability and applicability for other aromatic amines and heteroarenes containing different functional groups.

Method for continuously synthesizing alicyclic carbamate

The invention relates to a method for continuously synthesizing alicyclic carbamate. The method comprises the following steps: preheating raw material gas and raw material liquid to 20-130 DEG C through a preheater, introducing the raw material gas and the raw material liquid into a fixed bed reactor filled with a supported metal catalyst, and reacting at 30-150 DEG C under the reaction pressure of 0-5 MPa to obtain the alicyclic carbamate, wherein the supported metal catalyst comprises an active component metal salt and a carrier, and the active component metal salt is a rhodium active component metal salt. The method has the advantages of high mass and heat transfer efficiency, short reaction time, high product selectivity, intrinsic safety, high space-time efficiency and the like.

Method for synthesizing alicyclic carbamate by taking isopropanol as hydrogen source

The invention relates to a method for synthesizing alicyclic carbamate by taking isopropanol as a hydrogen source. The method comprises the following steps: in a high-pressure reaction kettle, under N2 atmosphere, taking aromatic carbamate as a substrate, adding a reaction solvent and a catalyst; and taking isopropanol as a hydrogen source, performing stirring and reaction for 2-24 hours under the conditions of 50-200 DEG C and 0-5 MPa to obtain the alicyclic carbamate. The catalyst is a supported metal catalyst and comprises an active component metal salt and a carrier. The method has the advantages of mild reaction conditions, high safety, easiness in operation and the like.

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.

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

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.

Urethanes synthesis from oxamic acids under electrochemical conditions

Urethane synthesis via oxidative decarboxylation of oxamic acids under mild electrochemical conditions is reported. This simple phosgene-free route to urethanes involves an in situ generation of isocyanates by anodic oxidation of oxamic acids in an alcoholic medium. The reaction is applicable to a wide range of oxamic acids, including chiral ones, and alcohols furnishing the desired urethanes in a one-pot process without the use of a chemical oxidant.

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.