107-69-7

Usage

Safety Profile

Moderately toxic by ingestion andintraperitoneal routes. Questionable carcinogen withexperimental neoplastigenic data. Mutation data reported.When heated to decomposition it emits very toxic fumesof Clí and NOx.

InChI:InChI=1/C3H4Cl3NO2/c4-3(5,6)1-9-2(7)8/h1H2,(H2,7,8)

Upstream product

• 75-44-5 phosgene 
• 115-20-8 1,1,1-trichloroethanol 
• 463-72-9 carbamic chloride 
• 917-61-3 sodium isocyanate 
• 7647-01-0 hydrogenchloride 
• 81207-65-0 4-dimethylamino-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one; compound with carbamic acid-(β.β.β-trichloro-ethyl ester) 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 17341-93-4 2,2,2-Trichloroethyl chloroformate 
• 931109-52-3 O-tosyl-N-trichloroethoxycarbonylhydroxylamine 
• 120542-16-7 benzyl 2,2,2-trichloroethylimidodicarbonate 

Downstream Products

• 100038-78-6 1-(2,2,2-Trichloro-ethoxycarbonylamino)-cyclohex-2-enecarboxylic acid methyl ester 
• 756839-59-5 3-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-1-[5-fluoro-2-(1-methyl-1H-indazol-5-yloxy)-benzyl]-1-methylurea 
• 756839-66-4 1-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[5-fluoro-2-(1-methyl-1H-pyrazolo[3,4-c]pyridin-5-yloxy)-benzyl]-urea 
• 1309440-11-6 2,2,2-trichloroethyl 1-(methoxycarbonyl)-1,2-diphenyl-2-(phenylamino)ethylcarbamate 
• 122210-05-3 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose 
• 122210-01-9 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 
• 136945-13-6 [(2R,3S,4R,5R)-3,4-diacetoxy-6-hydroxy-5-(2,2,2-trichloroethoxycarbonylamino)tetrahydropyran-2-yl]methyl acetate 
• 1380423-62-0 (E)-2,2,2-trichloroethyl 4-phenylbut-3-en-2-ylcarbamate 
• 756839-64-2 3-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-1-[5-fluoro-2-(1-methyl-1H-indazol-5-yloxy)-benzyl]-1-(4-methoxybenzyl)-urea 
• 756839-42-6 1-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[5-fluoro-2-(1-methyl-1H-indazol-5-yloxy)-benzyl]urea 
• 81207-65-0 4-dimethylamino-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one; compound with carbamic acid-(β.β.β-trichloro-ethyl ester) 

Relevant academic research and scientific papers

Iridium-Catalyzed Amidation of in Situ Prepared Silyl Ketene Acetals to Access α-Amino Esters

Disclosed herein is a convenient Ir-catalyzed amidation of esters to access α-amido esters. Initially prepared silyl ketene acetals are directly employed, without separate purification, for subsequent amidation with an oxycarbonylnitrenoid precursor using the Cp*(LX)Ir(III) catalyst. The α-amidation was facile for both α-aryl and α-alkyl esters. Density functional theory studies revealed that the generation of a putative Ir-nitrenoid is facilitated by the chelation of the countercation additive during the N-O bond cleavage of the nitrene precursor.

Metal-Free Stereoselective Synthesis of (E)- And (Z)-N-Monosubstituted β-Aminoacrylates via Condensation Reactions of Carbamates

N-monosubstituted β-aminoacrylates are building blocks, which have been used in the preparation of amino acids and pharmaceuticals. Two efficient, stereoselective methods of preparation, via acid- or base-promoted condensation reactions of carbamates, are described. The base-promoted reaction is E-selective, while acid catalysis can, through the choice of solvent, selectively form E or Z. The acid-catalyzed E-selective process proceeds through a crystallization obviating the need for chromatographic purification.

Copper-catalyzed oxidative benzylic C(sp3)-H amination: Direct synthesis of benzylic carbamates

A new efficient strategy to access benzylic carbamates through C-H activation is reported. The use of a catalytic amount of a Cu(i)/diimine ligand in combination with NFSI ((PhSO2)2NF) or F-TEDA-PF6 as oxidants and H2NCO2R as an amine source directly leads to the C-N bond formation at the benzylic position. The mild reaction conditions and the broad substrate scope make this transformation a useful method for the late-stage incorporation of a ubiquitous carbamate fragment onto hydrocarbons. This journal is

Synthesis of 8-Aminoquinolines by Using Carbamate Reagents: Facile Installation and Deprotection of Practical Amidating Groups

Described herein is the development of practical routes to 8-aminoquinolines by using readily installable and easily deprotectable amidating reagents. Two scalable procedures were optimized under RhIII-catalyzed conditions: i) the use of pre-generated chlorocarbamates and ii) a two-step one-pot process that directly employs carbamates. Both approaches are highly convenient for the gram-scale synthesis of 8-aminoquinolines under mild conditions. Facile deprotection of the synthetically versatile amidating groups was achieved under the Pd-catalyzed transfer hydrogenation conditions with simultaneous deoxygenation of quinoline N-oxides, thus yielding 8-aminoquinolines in excellent overall efficiency.

Direct, intermodular, enantioselective, iridium-catalyzed allylation of carbamates to form carbamate-protected, branched allylic amines

The direct reaction between carbamates and achiral allylic carbonates to form branched, conveniently protected primary allylic amines with high regioseiectivity and enantioselectivity Is reported. This process occurs without base or with 0.5 equiv K3PO4 In the presence of a metalacyclic iridium catalyst containing a labile ethylene ligand. The reactions of aryl-, heteroaryl-, and alkyl-substituted allylic carbonates with BocNH 2, FmocNH2, CbZNH2, TrocNH2, TeocNH2, and 2-oxazolidinone occur In good yields, with high selectivity for the branched isomer and high enantioselectivities (98% average ee).

N-tosyloxycarbamates as reagents in rhodium-catalyzed C-H amination reactions

Metal nitrenes for use in C-H insertion reactions were obtained from N-tosyloxycarbamates in the presence of an inorganic base and a rhodium(II) dimer complex catalyst. The C-H amination reaction proceeds smoothly, and the potassium tosylate that forms as a byproduct is easily removed by filtration or an aqueous workup. This new methodology allows the amination of ethereal, benzylic, tertiary, secondary, and even primary C-H bonds. The intramolecular reaction provides an interesting route to various substituted oxazolidinones, whereas the intermolecular reaction gives trichloroethoxycarbonyl-protected amines that can be isolated with moderate to excellent yields and that cleave easily to produce the corresponding free amine. The development, scope, and limitations of the reactions are discussed herein. Isotopic effects and the electronic nature of the transition state are used to discuss the mechanism of the reaction.

Polar cycloaddition of monocyclic 1,2-thiazinylium salt and transformation of the cycloadducts to 1,2-azathiabenzenes

Deprotonation of the cycloadducts, which were newly obtained from polar cycloaddition of monocyclic 1,2-thiazinylium salt with 1,3-butadienes, with a strong base provided 1,2-azathiabenzenes having sulfur at a bridgehead position.

Convenient Preparation of Alkyl Benzyl Imidodicarbonates, Useful Reagents for the Direct Synthesis of Protected Amines

New mixed alkyl benzyl imidodicarbonates were prepared by reaction of benzyloxycarbonyl isocyanate with appropriate alcohols.This simple procedure also furnished alternative, more convenient routes to dibenzyl and benzyl 9-fluorenylmethyl imidodicarbonates.The substances are of interest as potential Gabriel reagents.Completely selective removal of one of the alkoxycarbonyl groups from the N-atom of the imidodicarbonates was demonstrated in several instances, giving benzyl carbamate or the alternative carbamate.

Process for the preparation of 3-carbamoyl cephalosporins using isocyanates

Alcohols are reacted with certain isocyanate compounds to produce the N-substituted carbamoyloxy derivatives which are cleaved to obtain the carbamate.