21667-62-9

Usage

Uses

Used in Pharmaceutical Industry:
3-Chlorobenzoylacetonitrile is used as an intermediate in the synthesis of various pharmaceuticals. It plays a crucial role in the production of drugs due to its ability to form carbon-carbon and carbon-nitrogen bonds, which are essential in the creation of complex molecular structures.
Used in Agrochemical Industry:
In the agrochemical industry, 3-Chlorobenzoylacetonitrile is utilized as an intermediate for the synthesis of various agrochemicals. Its reactivity and ability to form specific chemical bonds make it a valuable component in the development of effective agricultural products.
Used in Organic Chemistry Research:
3-Chlorobenzoylacetonitrile is used as a reagent in organic chemistry reactions. It is particularly useful in the formation of carbon-carbon and carbon-nitrogen bonds, which are fundamental in the synthesis of a wide range of organic compounds. Its versatility makes it a popular choice for researchers in the field of organic chemistry.

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

Upstream product

• 2905-65-9 methyl 3-chlorobenzoate 
• 75-05-8 acetonitrile 
• 1128-76-3 3-chloro-benzoic acid ethyl ester 
• 618-46-2 m-Chlorobenzoyl chloride 
• 372-09-8 cyanoacetic acid 
• 107818-32-6 (Z)-3-Chloro-3-(3-chloro-phenyl)-acrylonitrile 
• 1224257-72-0 3-(3-chlorophenyl)-3-chloropropenal 
• 63503-60-6 3-chlorophenylboronic acid 
• 109-77-3 malononitrile 
• 13138-21-1 diazoacetonitrile 
• 587-04-2 m-Chlorobenzaldehyde 
• 7677-24-9 trimethylsilyl cyanide 
• 873-63-2 m-chlorobenzyl alcohol 
• 773837-37-9 sodium cyanide 

Downstream Products

• 100246-30-8 α-(3-Chlorobenzoyl)acetamide 
• 847950-00-9 1-[2-amino-3-(3-chloro-benzoyl)-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-ethanone 
• 836684-69-6 2-(3-chlorobenzoyl)-3-phenylaminoacrylonitrile 
• 522629-12-5 (R)-3-hydroxy-3-(3’-chlorophenyl)-propanenitrile 
• 1370042-91-3 (E)-2-(3-chlorobenzoyl)-3-(4-(dimethylamino)phenyl)acrylonitrile 
• 1416903-38-2 C₁₄H₇ClN₄O₂S 

Relevant academic research and scientific papers

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.

Asymmetric Hydroacylation Involving Alkene Isomerization for the Construction of C3-Chirogenic Center

A new transformation pattern for enantioselective intramolecular hydroacylation has been developed involving an alkene isomerization strategy. Proceeding through a five-membered rhodacycle intermediate, 3-enals were converted to C3- or C3,C5-chirogenic cyclopentanones with satisfactory yields, diastereoselectivities, and enantioselectivities. A catalytic cycle has been theoretically calculated and the origin of the stereoselection is rationally explained.

Deadly KCN and pricey metal free track for accessing β-ketonitriles employing mild reaction conditions

A one pot synthesis of β-ketonitriles from readily accessible 3-chloropropenals using economically benign iodine, aqueous ammonia and sodium hydroxide solution, employing mild reaction conditions have been described. This report presents a convenient, inexpensive, highly toxic-matter-free and eco-friendly approach for β-ketonitriles.

Selective Synthesis of β-Ketonitriles via Catalytic Carbopalladation of Dinitriles

A practical, convenient, and highly selective method of synthesizing β-ketonitriles from the Pd-catalyzed addition of organoboron reagents to dinitriles has been developed. This method provides excellent functional-group tolerance, a broad scope of substrates, and the convenience of using commercially available substrates. The method is expected to show further utility in future synthetic procedures.

COMPOUNDS AND METHODS FOR TREATING CANCER

Compounds useful as modulators of AhR, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or ameliorate AhR-mediated disorders such as cancers and inflammatory diseases are provided.

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.

HETEROCYCLE SUBSTITUTED AMINO-PYRIDINE COMPOUNDS AND METHODS OF USE THEREOF

The present disclosure relates to heterocycle substituted amino-pyridine compounds. The present disclosure also relates to pharmaceutical compositions containing these compounds and methods of treating cancer by administering these compounds and pharmaceutical compositions to subjects in need thereof. The present disclosure also relates to the use of such compounds for research or other non-therapeutic purposes.

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.

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.