39546-47-9

Usage

Uses

Used in Pharmaceutical Industry:
1-CHLORO-4-(ISOCYANOMETHYL)BENZENE is used as a key intermediate in the synthesis of various pharmaceutical compounds for its ability to facilitate the creation of complex molecular structures that can target specific biological pathways.
Used in Agrochemical Industry:
In the agrochemical sector, 1-CHLORO-4-(ISOCYANOMETHYL)BENZENE is utilized as a precursor in the development of pesticides and other crop protection agents, contributing to the production of effective and targeted chemical solutions for agricultural use.
Used in Advanced Materials Industry:
1-CHLORO-4-(ISOCYANOMETHYL)BENZENE is employed as a component in the formulation of advanced materials, such as polymers and composites, due to its potential to enhance properties like strength, durability, and chemical resistance.
Used in Dyes and Pigments Industry:
1-CHLORO-4-(ISOCYANOMETHYL)BENZENE is used as a starting material in the production of dyes and pigments, where its unique chemical structure allows for the creation of vibrant colors and stable formulations for various applications, including textiles, plastics, and printing inks.
Safety Note:
Given the toxic and harmful properties of 1-CHLORO-4-(ISOCYANOMETHYL)BENZENE, it is imperative to handle and store this chemical with the utmost care, adhering to safety protocols to prevent accidental exposure through ingestion, inhalation, or skin contact.

InChI:InChI=1/C8H6ClN/c1-10-6-7-2-4-8(9)5-3-7/h2-5H,6H2

Upstream product

• 86386-67-6 N-(4-chlorobenzyl)formamide 
• 31694-96-9 (4-chloro-benzyl)-(1⁽²⁾H-tetrazol-5-yl)-amine 
• 104-88-1 4-chlorobenzaldehyde 
• 7677-24-9 trimethylsilyl cyanide 
• 622-95-7 4-chlorobenzyl bromide 
• 67-66-3 chloroform 
• 104-86-9 4-chlorobenzylamine 

Downstream Products

• 39533-35-2 α-Isocyano-p-chlorphenylessigsaeureaethylester 
• 1198116-48-1 N-[(4-chlorophenyl)methyl]-3-oxo-2-(2-pyridin-2-ylethyl)-1H-isoindole-1-carboxamide 
• 1373521-23-3 2-((2-(3-fluorobenzylthio)pyrimidin-4-yl)(2-methoxyethyl)amino)-N-(4-chlorobenzyl)-4-methylpentanamide 
• 1373521-09-5 N-(4-chlorobenzyl)-2-(allyl(2-(benzylthio)pyrimidin-4-yl)amino)-4-methylpentanamide 
• 140-53-4 p-chlorobenzyl cyanide 
• 100-47-0 benzonitrile 
• 106-43-4 para-chlorotoluene 

Relevant academic research and scientific papers

Solid phase-mediated synthesis of isonitriles

Supported sulfonyl chlorides and microwave irradiation are an efficient combination for isonitrile synthesis.

Anodic Oxidation of Aminotetrazoles: A Mild and Safe Route to Isocyanides

A new electrochemical method for the preparation of isocyanides from easily accessible aminotetrazole derivatives has been developed, which tolerates an unprecedented range of functional groups. The use of chemical, rather than electrochemical, oxidation to afford isocyanides was also demonstrated, which provides access to these compounds for those without electrosynthesis equipment. The practicality of scale-up using flow electrochemistry has been demonstrated, in addition to the possibility of using electrochemically generated isocyanides in further reactions.

Isocyanide 2.0

The isocyanide functionality due to its dichotomy between carbenoid and triple bond characters, with a nucleophilic and electrophilic terminal carbon, exhibits unusual reactivity in organic chemistry exemplified for example in the Ugi reaction. Unfortunately, the over proportional use of only a few isocyanides hampers novel discoveries about the fascinating reactivity of this functional group. The synthesis of a broad range of isocyanides with multiple functional groups is lengthy, inefficient, and exposes the chemist to hazardous fumes. Here we present an innovative isocyanide synthesis overcoming these problems by avoiding the aqueous workup which we exemplify by parallel synthesis from a 0.2 mmol scale performed in 96-well microtiter plates up to a 0.5 mol multigram scale. The advantages of our methodology include an increased synthesis speed, very mild conditions giving access to hitherto unknown or highly reactive classes of isocyanides, rapid access to large numbers of functionalized isocyanides, increased yields, high purity, proven scalability over 5 orders of magnitude, increased safety and less reaction waste resulting in a highly reduced environmental footprint. For example, the hitherto believed to be unstable 2-isocyanopyrimidine, 2-acylphenylisocyanides and even o-isocyanobenzaldehyde could be accessed on a preparative scale and their chemistry was explored. Our new isocyanide synthesis will enable easy access to uncharted isocyanide space and will result in many discoveries about the unusual reactivity of this functional group. This journal is

One-step synthesis of N, N′-substituted 4-imidazolidinones by an isocyanide-based pseudo-five-multicomponent reaction

A pseudo-five-multicomponent reaction involving an isocyanide, a primary amine, two molecules of formaldehyde and water is reported, which gives N,N′-substituted 4-imidazolidinones when trifluoroethanol is used as the solvent. The reaction proceeds with good yields and with a wide variety of amines and isocyanides, providing an efficient new entry to these heterocycles. A preliminary study of the reaction mechanism suggests that trifluoroethanol, although acting as the solvent, is directly involved as a reagent in the reaction pathway.

Rational design and synthesis of 1,5-disubstituted tetrazoles as potent inhibitors of the MDM2-p53 interaction

Using the computational pharmacophore-based ANCHOR.QUERY platform a new scaffold was discovered. Potent compounds evolved inhibiting the protein-protein interaction p53-MDM2. An extensive SAR study was performed based on our four-point pharmacophore model

Novel ultrasound-promoted parallel synthesis of trifluoroatrolactamide library via a one-pot passerini/hydrolysis reaction sequence and their fungicidal activities

An ultrasound-promoted one-pot Passerini/hydrolysis reaction sequence has been developed for the synthesis of trifluoroatrolactamide derivatives using a diverse range of trifluoroacetophenones and isonitriles in acetic acid. Parallel synthesis in a centrifuge tube using a noncontact ultrasonic cell crusher was used in this study as an efficient method for the rapid generation of combinatorial trifluoroatrolactamide libraries, and subsequent biochemical evaluation of the resulting compounds indicated that they possessed excellent broad-spectrum fungicidal activities. N-(4-chlorophenyl)-2-(4-ethylphenyl)-3,3, 3-trifluoro-2-hydroxypropanamide and N-(4-chlorophenyl)-3,3,3-trifluoro-2- hydroxy-2-(4-methoxyphenyl)propanamide, in particular, showed significant fungicidal activities against all of the fungal species tested in the current study.

A convenient method for the preparation of benzyl isocyanides

Treatment of benzyl halides with silver salts (AgClO4, AgBF 4, or AgOTf) and trimethylsilyl cyanide (TMSCN) in CH 2Cl2 followed by cleavage of the carbon-silicon bond with aqueous NaHCO3 or TBAF directly afforded the corresponding isocyanides. Georg Thieme Verlag Stuttgart.

Trifluoropyruvamides from isocyanides and trifluoroacetic anhydride

Addition of trifluoroacetic anhydride to isocyanides proceeds smoothly to give after treatment trifluoropyruvamide derivatives in high yield.

3-Phenyl-substituted imidazo[1,5-a]quinoxalin-4-ones and imidazo[1,5- a]quinoxaline ureas that have high affinity at the GABA(A)/benzodiazepine receptor complex

A series of imidazo[1,5-a]quinoxalin-4-ones and imidazo[1,5- a]quinoxaline ureas containing substituted phenyl groups at the 3-position was developed. Compounds within the imidazo-[1,5-a]quinoxaline urea series had high affinity for the GABA(A)/benzodiaze