20668-13-7

Usage

Uses

Used in Agriculture:
(2-Chlorophenyl)carbamic acid methyl ester is used as an insecticide and acaricide for controlling pests such as mites, aphids, and caterpillars in various crops. It works by inhibiting the activity of the enzyme acetylcholinesterase, leading to the accumulation of acetylcholine in the synaptic cleft and ultimately causing paralysis and death in the targeted pests.
However, due to its toxicity and potential risks to human health and the environment, its use is regulated and restricted in many countries. It is important to handle and use this chemical with caution and in accordance with safety guidelines to minimize its impact on non-target organisms.

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

Upstream product

• 67-56-1 methanol 
• 3320-83-0 o-chlorophenyl isocyanate 
• 107840-17-5 C₁₃H₁₅ClN₂O₂ 
• 609-66-5 2-chlorobenzamide 
• 201230-82-2 carbon monoxide 
• 88-73-3 2-Chloronitrobenzene 
• 95-51-2 o-chloroaniline 
• 616-38-6 carbonic acid dimethyl ester 
• 79-22-1 methyl chloroformate 
• 168481-89-8 3,4-bis(2-chlorophenyl)-1,2,5-oxadiazole 2-oxide 

Downstream Products

• 35600-71-6 Chloromethyl-(2-chloro-phenyl)-carbamic acid methyl ester 

Relevant academic research and scientific papers

Photochemical generation of nitric oxide from 3,4-Bis-2′-chlorophenylfuroxan

Photolysis of 3,4-bis-2′-chlorophenylfuroxan generated nitric oxide and bis-2-chlorophenylacetylene in 17% yield. This is the first example of the photochemical generation of the nitric oxide from the furoxan.

Zr-MOF-808@MCM-41 catalyzed phosgene-free synthesis of polyurethane precursors

In this work, a catalytic method is presented for the synthesis of aromatic carbamates from aromatic amines using dimethyl carbonate instead of phosgene as a green and safe reaction process. Microcrystalline Zr-MOF-808 is reported as an active and efficient heterogeneous catalyst for the selective carbamoylation of anilines and industrially relevant aromatic diamines, under mild reaction conditions with near quantitative yields. We have accomplished the selective growth of well-dispersed Zr-MOF-808 nanocrystals within the mesoporous material MCM-41. A superior catalytic performance of the Zr-MOF-808@MCM-41 is demonstrated that together with increased stability stands out as an advantageous heterogeneous catalyst for polyurethane production. In situ FTIR studies have allowed a better understanding of the reaction pathway at the molecular level when the active MOF catalyst is present.

Chiral Bifunctional Phosphine-Carboxylate Ligands for Palladium(0)-Catalyzed Enantioselective C?H Arylation

Previous enantioselective Pd0-catalyzed C?H activation reactions proceeding via the concerted metalation-deprotonation mechanism employed either a chiral ancillary ligand, a chiral base, or a bimolecular mixture thereof. This study describes th

Palladium-Catalyzed Carbamate-Directed Regioselective Halogenation: A Route to Halogenated Anilines

This study describes an efficient method for ortho-selective halogenation of N-arylcarbamates under mild conditions for the first time. Although being weakly coordinating, N-arylcarbamates act very well as a removable directing group for activation of C-H bonds. The developed procedure results in extremely valuable halogenated N-arylcarbmates that can further be hydrolyzed to halogenated anilines. The obtained reaction conditions showed broad scope and wide functional group tolerance. All the products were formed in good yields with extremely high selectivity.

(Tosylimino)phenyl-λ3-iodane as a reagent for the synthesis of methyl carbamates via hofmann rearrangement of aromatic and aliphatic carboxamides

A new, mild procedure for the Hofmann rearrangement of aromatic and aliphatic carboxamides using (tosylimino)phenyl-λ3-iodane, PhINTs, as a reagent is reported. Because of the mild reaction conditions, this method is particularly useful for the Hofmann rearrangement of substituted benzamides, which usually afford complex reaction mixtures with other hypervalent iodine oxidants. The mild reaction conditions and high selectivity in the reaction of carboxamides with PhINTs allow the isolation of the initially formed labile isocyanates or their subsequent conversion to stable carbamates by treatment with alcohols.

Efficient synthesis of methyl carbamate via Hofmann rearrangement in the presence of TsNBr2

An efficient method has been developed for the synthesis of carbamates from the corresponding amides via the Hofmann rearrangement using N,N-dibromo-p-toluenesulfonamide (TsNBr2) in the presence of DBU in methanol. The reaction goes into completion in 10-20 min at 65 °C to produce the corresponding carbamate in excellent yield.

Palladium-catalyzed carbonylation of amines: Switchable approaches to carbamates and N,N′-disubstituted ureas

Switchable access to carbamates and ureas has been developed by solvent control palladium-catalyzed carbonylation of aromatic amines under an atmosphere of carbon monoxide. A variety of N-phenylcarbamates and N,N′- diphenylureas was easily synthesized in good to excellent yields from readily available aromatic amines under mild conditions. Copyright

Synthesis of aryl urea derivatives from aryl amines and aryl isocyanates

The present study describes the synthesis of novel diaryl urea derivatives derived from aryl amine and aryl isocyanates. The synthesized compounds are analogs of sorafenib [4-[4-[[[4-chloro-3-(trifluoromethyl)phenyl]amino]carbonyl] amino]phenoxy]-N-methylpyridine-2- carboxamide] having potential antiproliferative activity.

Synthesis of methyl-1-(tert -butoxycarbonylamino)-2- vinylcyclopropanecarboxylate via a hofmann rearrangement utilizing trichloroisocyanuric acid as an oxidant

A trichloroisocyanuric acid (TCCA) mediated Hofmann rearrangement was utilized to synthesize methyl-1-(tert-butoxycarbonylamino)-2- vinylcyclopropanecarboxylate. A variety of functional groups are tolerated in this reaction including vinyl, cyclopropyl, pyridyl, aryl, benzyl, and nitro groups.

4-ALKYL-2-HALOANILINE DERIVATIVE AND PROCESS FOR PRODUCING THE SAME

The present invention relates to a compound of formula (1), wherein R1, R2, R3, n, and X are as defined in the specification, and a process for producing the same. This compound is useful as an intermediate for the synthes