40018-25-5

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Chlorobenzoylacetonitrile is used as a key intermediate in the synthesis of Clotiazepam, a pharmaceutical compound with anxiolytic, sedative, and muscle relaxant properties. Its role in the production process is crucial for creating an effective medication to treat anxiety and related conditions.
Used in Hair Dye Production:
In the cosmetic industry, 2-Chlorobenzoylacetonitrile is used as a compound commonly found in brown and black hair dyes. Its presence in these hair dyes contributes to the coloration process, providing a lasting and vibrant result for users seeking to change or enhance their hair color.
Chemical Properties:
As a yellowish solid, 2-Chlorobenzoylacetonitrile possesses distinct chemical properties that make it suitable for various applications in different industries. Its versatility and reactivity in chemical reactions are essential factors in its widespread use.

InChI:InChI=1/C9H6ClNO/c10-8-4-2-1-3-7(8)9(12)5-6-11/h1-4H,5H2

Upstream product

• 610-96-8 methyl chlorobenzoate 
• 75-05-8 acetonitrile 
• 7335-25-3 ethyl 2-chlorobenzoate 
• 35022-42-5 2-chlorobenzoyl cyanide 
• 590-17-0 cyanomethyl bromide 
• 873-32-5 2-Chlorobenzonitrile 
• 609-65-4 o-chlorobenzoyl chloride 
• 372-09-8 cyanoacetic acid 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 289686-74-4 2‐chloro‐N‐methoxy‐N‐methylbenzamide 
• 13138-21-1 diazoacetonitrile 
• 89-98-5 2-chloro-benzaldehyde 
• 773837-37-9 sodium cyanide 
• 5000-66-8 2-chlorophenacyl bromide 

Downstream Products

• 67985-47-1 3-(2-chloro-phenyl)-3-oxo-2-(3-phenyl-thiazolidin-2-ylidene)-propionitrile 
• 53882-59-0 Dithiophosphoric acid O-[(E)-1-(2-chloro-phenyl)-2-cyano-vinyl] ester O'-ethyl ester S-propyl ester 
• 40017-58-1 2-Amino-3-(o-chlorobenzoyl)-thiophene 
• 129587-18-4 3-(2-Chloro-phenyl)-3-oxo-2-pyrrolidin-(2Z)-ylidene-propionitrile 
• 129587-17-3 2-Azepan-(2Z)-ylidene-3-(2-chloro-phenyl)-3-oxo-propionitrile 
• 130312-24-2 2-amino-3-(2-chlorobenzoyl)-6-acetyl-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine 
• 100827-76-7 diethyl 2-[[5-amino-4-(2-chlorobenzoyl)-thien-2-yl]methyl]malonate 
• 50508-60-6 2-amino-3-(2-chlorobenzoyl)-5-ethylthiophene 
• 133550-23-9 (E)-2-(2-Chloro-benzoyl)-3-(3,4-dihydroxy-phenyl)-acrylonitrile 
• 120135-52-6 2-amino-3-(2-chlorobenzoyl)-5-octylthiophene 
• 120135-46-8 2-amino-3-(2-chlorobenzoyl)-5-decylthiophene 
• 120135-37-7 2-amino-3-(2-chlorobenzoyl)-5-hexylthiophene 
• 120135-61-7 2-amino-3-(2-chlorobenzoyl)-5-dodecylthiophene 
• 120135-64-0 2-amino-3-(2-chlorobenzoyl)-5-hexadecylthiophene 

Relevant academic research and scientific papers

Efficient Syntheses of Diverse, Medicinally Relevant Targets Planned by Computer and Executed in the Laboratory

The Chematica program was used to autonomously design synthetic pathways to eight structurally diverse targets, including seven commercially valuable bioactive substances and one natural product. All of these computer-planned routes were successfully executed in the laboratory and offer significant yield improvements and cost savings over previous approaches, provide alternatives to patented routes, or produce targets that were not synthesized previously. Although computers have demonstrated the ability to challenge humans in various games of strategy, their use in the automated planning of organic syntheses remains unprecedented. As a result of the impact that such a tool could have on the synthetic community, the past half century has seen numerous attempts to create in silico chemical intelligence. However, there has not been a successful demonstration of a synthetic route designed by machine and then executed in the laboratory. Here, we describe an experiment where the software program Chematica designed syntheses leading to eight commercially valuable and/or medicinally relevant targets; in each case tested, Chematica significantly improved on previous approaches or identified efficient routes to targets for which previous synthetic attempts had failed. These results indicate that now and in the future, chemists can finally benefit from having an “in silico colleague” that constantly learns, never forgets, and will never retire. Multistep synthetic routes to eight structurally diverse and medicinally relevant targets were planned autonomously by the Chematica computer program, which combines expert chemical knowledge with network-search and artificial-intelligence algorithms. All of the proposed syntheses were successfully executed in the laboratory and offer substantial yield improvements and cost savings over previous approaches or provide the first documented route to a given target. These results provide the long-awaited validation of a computer program in practically relevant synthetic design.

One-pot dichlorinative deamidation of primary β-ketoamides

An approach to the dichlorinative deamidation of primary β-ketoamides through ketonic cleavage is described, and a series of α,α-dichloroketones were furnished mostly in the presence of TEMPO. Based on control experiments, a mechanism involving tandem dichlorination and deamidation is proposed to interpret the observed reactivity.

SeO2-Mediated One-Pot Synthesis of 3-Cyanofurans from 3-Oxo-3-arylpropanenitriles and Substituted Acetaldehydes

An SeO2-mediated one-pot method was established for the synthesis of 3-cyanofurans from 3-oxo-3-arylpropanenitriles and substituted acetaldehydes. The generality of the reaction was explored, and a plausible mechanism is proposed.

Chemoselective efficient synthesis of functionalized β-oxonitriles through cyanomethylation of Weinreb amides

A synthesis of β-oxonitriles is reported via the generation of R1R2CLiCN species followed by the trapping with variously decorated Weinreb amides. The optimization study revealed that lithiation of acetonitriles is best accomplished by deprotonation with MeLi-LiBr at low temperature. The protocol can be conveniently adapted to the synthesis of α-mono or α,α-disubstituted cyanoketones. 15N- and 17O-NMR data are reported for selected compounds. This journal is

Chemo- And stereoselective reduction of β-keto-α-oximino nitriles by using baker's yeast

The baker's yeast mediated reduction of β-keto-α-oximino nitriles 3 at 20 ° C gave β-hydroxy-α-oximino nitriles 4 in high yields with high enantiomeric purity [enantiomeric excess (ee) values >99%]. At room temperature, the same reaction afforded the product in a slightly lower yield. The β-hydroxy-α-oximino nitriles 4 were obtained as single stereoisomers according to chiral GC-MS analyses and the 1H and 19F NMR spectra of the corresponding Mosher esters. The abso-lute stereochemistry of alcohol 4a was determined by hydrolysis of its oximino nitrile group followed by conversion into its corresponding α-hydroxy ester. The β-hydroxy-α-oximino nitrile products were further submitted to oxime- and nitrileselective transformations. This chemo- and stereoselective reduction can be used to generate important chiral building blocks.

Pyrazolotriazines as inhibitors of nucleases

The invention provides compounds represented by the structural formula (1): wherein R1, R2, R3 and R4 are as defined in the claims. The compounds are inhibitors of nucleases, and are useful in particular in a method of treatment and/or prevention of proliferative diseases, neurodegenerative diseases, and other genomic instability associated diseases.

WNT PATHWAY MODULATORS

The present invention relates to dihydropyrazolo[l,5-a]pyrimidine compounds of formula I, defined herein, as WNT pathways modulators, processes for making them, and pharmaceutical compositions comprising them. Methods of treatment of conditions mediated by WNT pathway signalling including cancer, fibrosis, stem cell and diabetic retinopathy, rheumatoid arthritis, psoriasis and myocardial infarction, comprising the compounds of formula I are also provided.

Umpolung Strategy for Synthesis of β-Ketonitriles through Hypervalent Iodine-Promoted Cyanation of Silyl Enol Ethers

An efficient method to synthesize β-ketonitriles from silyl enol ethers by an umploung hypervalent iodine(III)-CN species generated in situ from PhIO/BF3·Et2O/TMSCN has been developed for the first time. This method can be applied to structurally diverse aromatic and aliphatic substrates and further extended to preparation of bioactive compounds like 5-aminopyrazole and 5-aminoisoxazole.

Specific 1,2-Hydride Shift in the Boron Trifluoride Catalyzed Reactions of Aromatic Aldehydes with Diazoacetonitrile: Simple Synthesis of β-Ketonitriles

A series of β-ketonitriles was synthesized within 30 min under mild conditions through the BF3 ·OEt2-catalyzed addition reactions of diazoacetonitrile to aromatic aldehydes and subsequent 1,2-hydride shift. This method is advantageous in that it is operationally simple, mild and metal-free conditions are used, the substrate scope is wide, and the products are obtained in moderate to high yields (up to 81 %). Additionally, γ,δ-unsaturated β-ketonitriles are also accessible by this method by using cinnamaldehydes.

Cascade synthesis of 3-aza-bicyclo[3.1.0]hex-2-ene derivatives from N-allyl enamines

An efficient iodine-mediated cascade synthesis of 3-aza-bicyclo[3.1.0]hex-2-ene derivatives from easily prepared N-allyl enamines has been developed. The advantages of the reaction include facilitative preparation of substrates 3a-t, good functional group tolerance and transition-metal-free conditions.