592-35-8

Usage

Chemical Properties

WHITE FLAKES

Flammability and Explosibility

Notclassified

Safety Profile

A poison via intraperitoneal route. Moderately toxic via subcutaneous route. Experimental teratogenic effects. Questionable carcinogen with experimental neoplastigenic data. Mutation data reported. See also CARBAMATES. When heated to decomposition it emits toxic fumes of NOx

InChI:InChI=1/C5H11NO2/c1-2-3-4-6-5(7)8/h6H,2-4H2,1H3,(H,7,8)/p-1

Upstream product

• 592-34-7 carbonochloridic acid, butyl ester 
• 57-13-6 urea 
• 71-36-3 butan-1-ol 
• 420-05-3 cyanic acid 
• 4747-87-9 isopropenyl isocyanate 
• 16326-62-8 nitrobiuret 
• 590-28-3 potassium cyanate 
• 143-33-9 sodium cyanide 
• 90714-03-7 C₈H₁₄N₂O₄ 
• 5663-07-0 hydroxy sulfonylurea 
• 917-61-3 sodium isocyanate 
• 110-82-7 cyclohexane 
• 149552-43-2 [N-(nosyl)imino]phenyliodinane 
• 3147-85-1 allophanic acid butyl ester 

Downstream Products

• 108-80-5 isocyanuric acid 
• 71-36-3 butan-1-ol 
• 141-72-0 acetone-dibutylacetal 
• 96900-99-1 4-(α-butoxy-isopropyl)-allophanic acid butyl ester 
• 2533-21-3 Bis(butyloxycarbonylamino)methan 
• 41142-14-7 Butoxycarbonylamino-(4-nitro-benzenesulfonyl)-acetic acid 
• 41142-22-7 Butoxycarbonylamino-(2,5-dichloro-benzenesulfonyl)-acetic acid 
• 41142-00-1 Butoxycarbonylamino-(3,4-dichloro-benzenesulfonyl)-acetic acid 
• 74797-20-9 (5,11-Dihydro-10-thia-dibenzo[a,d]cyclohepten-5-yl)-carbamic acid butyl ester 
• 3147-85-1 allophanic acid butyl ester 
• 13896-06-5 4-ethyl-2-oxazolidinone 
• 439584-65-3 4-(1,2-dihydroxyethyl)phenyl acetate 
• 110599-45-6 N-(α-butoxycarbonylamino-α-methoxy)acetyltyramine 
• 110599-39-8 bisbutoxycarbonylamino-p-methylacetanilide 

Relevant academic research and scientific papers

Green and efficient synthesis of thioureas, ureas, primary: O -thiocarbamates, and carbamates in deep eutectic solvent/catalyst systems using thiourea and urea

An efficient and general catalysis process was developed for the direct preparation of various primary O-thiocarbamates/carbamates as well as monosubstituted thioureas/ureas by using thiourea/urea as biocompatible thiocarbonyl (carbonyl) sources. This procedure used choline chloride/tin(ii) chloride [ChCl][SnCl2]2 with a dual role as a green catalyst and reaction medium to afford the desired products in moderate to excellent yields. Moreover, the DES can be easily recovered and reused for seven cycles with no significant loss in its activity. Besides, the method shows very good performance for synthesizing the desired products on a large scale.

PROCESS FOR THE SYNTHESIS OF ISOCYANATE-FREE OMEGA-HYDROXY-URETHANES, ALPHA-OMEGA-DIURETHANES AND OLIGO (POLY)URETHANES

The synthesis of omega-hydroxyalkyl-urethanes, and of alfa-omega-diurethanes is reported which includes the reaction of diols with urea in presence of catalysts based on Ce at temperatures between 125 and 170°C over 4-8 h reaction time. A process for the production of oligomers of omega-hydroxyalkyl-urethanes is also reported based on the reaction of urea with diols in presence of Ce or Zr catalysts or Ce mixed oxides at 125-170°C over 4-20 h.

Preparation method of carbamate

The invention belongs to the technical field of synthesis of amino and carboxyl compounds connected to the same carbon frame through urea alcoholysis, and particularly relates to a preparation methodof carbamate. The preparation method of the carbamate comprises the following steps of: sequentially introducing urea, alcohol and a catalyst into a reactor, sealing, and reacting at 90-120 DEG C for8-12 hours to obtain the carbamate, wherein the catalyst includes an alumina supported metal oxide. By adopting the method for preparation of the carbamate, the side reaction of urea decomposition canbe effectively avoided, impurities such as carbamate are not detected, and the yield of the carbamate is high.

Triazinetriamine-derived porous organic polymer-supported copper nanoparticles (Cu-NPs@TzTa-POP): an efficient catalyst for the synthesis of: N -methylated products via CO2fixation and primary carbamates from alcohols and urea

In recent times, carbon dioxide fixation has received much attention for its potential application as an abundant C1 source and a range of important fine chemicals can be manufactured via this fixation. Here, a copper nanoparticle-decorated porous organic polymer-based (Cu-NPs@TzTa-POP) material was prepared by a simple in situ process. The catalyst was characterized by various techniques such as UV-vis spectra, FTIR spectra, HR-TEM, PXRD, N2 adsorption-desorption, TG-DTA, XPS, and AAS analysis. The synthesized heterogeneous catalyst showed excellent activity in an atmospheric carbon dioxide fixation reaction to produce N-methylated products from aromatic/heterocyclic amines in the presence of polymethyl-hydrosiloxane (PMHS) as the reducing agent at 80 °C within 12 h of the reaction. Through this catalytic N-methylation reaction, we obtained 98% yield of the product with turnover frequency ranging from 18 to 42 h-1. The catalyst is also very stable for the formation of primary carbamates from alcohols using the eco-friendly carbonylating agent, urea. Diverse alcohols (such as benzylic alcohols, phenols, heterocyclic alcohols, as well as aliphatic alcohols) showed much acceptance to this catalytic reaction and produced moderate to excellent yields of the respective carbamate products under ambient reaction conditions. Moreover, Cu-NPs@TzTa-POP is effortlessly recyclable and reusable without the extensive loss of active copper metal centres for many catalytic rounds (up to six catalytic rounds were examined).

An efficient one-pot synthesis of industrially valuable primary organic carbamates and: N -substituted ureas by a reusable Merrifield anchored iron(ii)-anthra catalyst [FeII(Anthra-Merf)] using urea as a sustainable carbonylation source

An efficient synthesis of primary carbamates and N-substituted ureas is explored with a newly developed heterogeneous polymer supported iron catalyst in the presence of a sustainable carbonylation source. The Merrifield anchored iron(ii)-anthra catalyst [FeII(Anthra-Merf)] was synthesized by functionalization of Merrifield polymer followed by grafting of iron metal. The catalyst [FeII(Anthra-Merf)] was characterized by several techniques, like SEM, EDAX, TGA, PXRD, XPS, FTIR, CHN, AAS and UV-Vis analysis. The designed polymer embedded [FeII(Anthra-Merf)] complex is a remarkably successful catalyst for the synthesis of primary organic carbamates and N-substituted ureas by using safe carbonylation agent urea with different derivatives of alcohols and amines, respectively. The reported catalyst is a potential candidate towards contributing a satisfactory yield of isolated products under suitable reaction conditions. The catalyst is recyclable and almost non-leaching in nature after six runs with an insignificant drop in catalytic activity. Thus we found an economical and viable catalyst [FeII(Anthra-Merf)] for primary carbamates and N-substituted urea synthesis under moderate reaction conditions.

An Fe3O4@SiO2/Schiff base/Cu(ii) complex as an efficient recyclable magnetic nanocatalyst for selective mono: N-arylation of primary O-alkyl thiocarbamates and primary O-alkyl carbamates with aryl halides and arylboronic acids

An efficient, convenient and novel method for the selective mono N-arylation of primary O-alkyl thiocarbamates and primary O-alkyl carbamates with aryl halides and arylboronic acids in the presence of a recyclable magnetic Cu(ii) nanocatalyst is described. A variety of mono N-arylated O-alkyl thiocarbamates and O-alkyl carbamates were prepared in good to excellent yields with a broad range of aryl coupling partners. The magnetic nanocatalyst can be easily recovered with an external magnetic field and reused at least five times without noticeable leaching or loss of its catalytic activity. This cost-effective and eco-friendly methodology has some other advantages, such as easy preparation of the catalyst, simple workup procedure, and easy purification, which makes this protocol interesting for the users in various fields of pharmacology and biotechnology systems.

Superparamagnetic Fe3O4 Nanoparticles in a Deep Eutectic Solvent: An Efficient and Recyclable Catalytic System for the Synthesis of Primary Carbamates and Monosubstituted Ureas

Superparamagnetic Fe3O4 nanoparticles were used to synthesize various primary carbamates as well as monosubstituted and N,N-disubstituted ureas. This efficient phosgene-free process used urea as an eco-friendly carbonyl source in the presence of a biocompatible deep eutectic solvent (DES) to provide an inexpensive and attractive route that afforded the products in moderate to excellent yields. The employed DES serves both a catalytic role and as the green reaction medium. The magnetic nanocatalyst and DES can been reused several times without a significant loss of activity.

Selective Synthesis of Secondary Arylcarbamates via Efficient and Cost Effective Copper-Catalyzed Mono Arylation of Primary Carbamates with Aryl Halides and Arylboronic Acids

Abstract: An efficient, selective and cost-effective procedure has been developed for mono N-arylation of primary alkyl and benzyl carbamates with aryl iodides and bromides by incorporating CuI as an inexpensive and commercially available catalyst. Despite previous reports on C–N coupling reactions, this process does not need expensive ligands and takes advantage of readily available and inexpensive ethylenediamine (EDA) as the ligand. Reaction times were relatively short and related N-arylated carbamates were obtained in excellent yields. Interestingly, replacing CuI with Cu(OAc)2 allowed us to use arylboronic acids as coupling partner for this reaction. All products are well characterized by 1H- and 13C-NMR, MS, melting point, IR and CHNS techniques.

Diaryl carbonate, method for producing same, and method for producing aromatic polycarbonate resin

Diaryl carbonate containing less than 1,000 mass ppm of a compound represented by formula (I), and a method for producing the diaryl carbonate. (In the formula, R1 is a hydrogen atom, halogen atom, alkyl group, alkoxy group, aryl group, or aryloxy group.).

METHOD FOR PRODUCING META-XYLYLENEDIISOCYANATES

A method for producing meta-xylylenediisocyanates includes a reaction step in which monohalogenated benzenes, formaldehydes, and an amide compound represented by general formula (1) below are allowed to react in the presence of an acidic liquid to produce a bisamide compound; a dehalogenation step in which in the bisamide compound, the halogen atom derived from the monohalogenated benzenes is replaced with a hydrogen atom; and a thermal decomposition step in which the bisamide compound from which the halogen atom is eliminated is subjected to thermal decomposition. In the reaction step, the acidic liquid contains inorganic acid, the equivalent ratio of the hydrogen atom of the inorganic acid relative to the monohalogenated benzenes is more than 14, the acidic liquid has an inorganic acid concentration of more than 90 mass %, and the reaction temperature is more than 10° C. [in-line-formulae]General formula (1):[/in-line-formulae] wherein R1 represents an alkoxy group or an amino group.