75746-71-3

Usage

Uses

2-Ethyl-6-methylphenyl isocyanate has a variety of applications across different industries due to its unique chemical properties. Some of its uses include:
Used in Pharmaceutical Industry:
2-Ethyl-6-methylphenyl isocyanate is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its reactive isocyanate group allows it to be used in the formation of urea and carbamate derivatives, which are important in the development of drugs with diverse therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 2-Ethyl-6-methylphenyl isocyanate is used as a building block for the synthesis of various agrochemicals, such as pesticides and herbicides. Its ability to form stable derivatives makes it a valuable component in the development of effective and environmentally friendly agrochemical products.
Used in Polymer Industry:
2-Ethyl-6-methylphenyl isocyanate is used as a monomer in the synthesis of polyurethane polymers. These polymers have a wide range of applications, including flexible and rigid foams, adhesives, coatings, and elastomers. The unique properties of the isocyanate group enable the formation of polymers with excellent mechanical, thermal, and chemical resistance properties.
Used in Research and Development:
2-Ethyl-6-methylphenyl isocyanate is also used as a research chemical in academic and industrial laboratories. Its reactivity and unique structure make it an interesting compound for studying various chemical reactions and exploring new synthetic routes for the development of novel materials and compounds.

InChI:InChI=1/C10H11NO/c1-3-9-6-4-5-8(2)10(9)11-7-12/h4-6H,3H2,1-2H3

Upstream product

• 124-38-9 carbon dioxide 
• 24549-06-2 6-ethyl-o-toluidine 
• 75-44-5 phosgene 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 55832-00-3 1-amidino-3-(2-methyl-6-ethylphenyl)urea 
• 1202526-46-2 1-(2-ethyl-6-methylphenyl)-3-(2-hydroxy-4-nitrophenyl)urea 
• 897340-51-1 C₁₈H₂₀N₂O₃ 
• 1627497-61-3 2-chloro-3-(2-ethyl-6-methylphenyl)quinazoline-4(3H)-one 

Relevant academic research and scientific papers

Palladium(0)-catalyzed carbon-Hydrogen bond functionalization for the synthesis of indoloquinazolinones

The indoloquinazolinone ring system has attracted considerable attention as a pharmacophore, because it shows various biological activities. The reported synthetic methods for the compound are simple and direct, but are not effective for the direct synthesis of indoloquinazolinone with a methylene group at the C-6 position. A palladium(0)-catalyzed cyclization of chloroquinazolinone via C-H functionalization was developed for a concise synthesis of indoloquinazolinone derivatives. The presence of a substituent at the C-6 position is important for obtaining the product in good yield. The conformation of the reaction intermediate, in particular the N-C-Pd bond angle, is important for the regioselectivity of the reaction.

Structural optimization of a CXCR2-directed antagonist that indirectly inhibits γ-secretase and reduces Aβ

Amyloid β (Aβ), a key molecule in the pathogenesis of Alzheimer's disease (AD), is derived from the amyloid precursor protein (APP) by sequential proteolysis via β- and γ-secretases. Because of their role in generation of Aβ, these enzymes have emerged as important therapeutic targets for AD. In the case of γ-secretase, progress has been made towards designing potent inhibitors with suitable pharmacological profiles. Direct γ-secretase inhibitors are being evaluated in clinical trials and new strategies are being explored to block γ-secretase activity indirectly as well. In this regard, we have previously reported an indirect regulation of γ-secretase through antagonism of CXCR2, a G-protein coupled receptor (GPCR). We demonstrated that N-(2-hydroxy-4-nitrophenyl)-N′-(2-bromophenyl)urea (SB225002), a selective inhibitor of CXCR2 also plays a role in an indirect inhibition of γ-secretase. Furthermore, we reported a ～5-fold difference in the selective inhibition of APP versus Notch processing via γ-secretase following treatment with SB225002. Herein we describe the synthesis and optimization of SB225002. By determination of the structure-activity relationship (SAR), we derived small molecules that inhibit Aβ40 production with IC50 values in the sub-micromolar range in a cell-based assay and also validated the potential of CXCR2 as a new target for therapeutic intervention in AD.

Preparation of isocyanates from primary amines and carbon dioxide using Mitsunobu chemistry

Primary alkylamines 1 and hindered arylamines 1 give high yields of isocyanates 5 when reacted with carbon dioxide and the Mitsunobu zwitterions 4 generated from dialkyl azodicarboxylates and Bu3P in dichloromethane at - 78°C. Use of Ph3P still gave high yields of isocyanates from reactions of primary alkylamines, but only low yields were obtained from reactions of aromatic amines. Reactions which failed to give high yields of isocyanates gave either carbamoylhydrazines 6 and/or dicarbamoylhydrazines 10 and/or triazolinones 7. The triazolinones were shown to arise from reactions of reactive aryl isocyanates with the Mitsunobu zwitterion. The carbamoylhydrazines were shown not to arise from reaction of isocyanate with reduced dialkyl azodicarboxylates, and a mechanism for their formation is proposed. Single-crystal X-ray analyses confirmed the structures of 6, 7, and 10.

A Mitsunobu-based procedure for the preparation of alkyl and hindered aryl isocyanates from primary amines and carbon dioxide under mild conditions

A Mitsunobu-based procedure for the preparation of alkyl and hindered aryl isocyanates in excellent yields from primary amines and carbon dioxide under very mild conditions is described.