17722-17-7

Basic information

• Product Name: 4'-CHLORO-2-CYANOACETANILIDE
• Synonyms: n-(4-chlorophenyl)-2-cyano-acetamid;4'-CHLORO-2-CYANOACETANILIDE;4-CHLORO-ALPHA-CYANOACETANILIDE;CBI-BB ZERO/005581;OTAVA-BB BB7110950309;P-CHLORO CYANO ACETANILIDE;N-(4-CHLOROPHENYL)-2-CYANOACETAMIDE;TIMTEC-BB SBB003598
• CAS NO: 17722-17-7
• Molecular Formula: C₉H₇ClN₂O
• Molecular Weight: 194.62
• EINECS: 241-720-7
• Product Categories: Amides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 17722-17-7.mol
• Article Data: 28

Chemical Properties

• Melting Point: 207-209 °C(lit.)
• Appearance: /
• CAS DataBase Reference: 4'-CHLORO-2-CYANOACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-CHLORO-2-CYANOACETANILIDE(17722-17-7)
• EPA Substance Registry System: 4'-CHLORO-2-CYANOACETANILIDE(17722-17-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 17722-17-7(Hazardous Substances Data)

Usage

General Description

4'-Chloro-2-cyanoacetanilide, also known as 4-chloro-2-cyanobenzoyl chloride, is a chemical compound with the molecular formula C9H8ClNO. It is a crystalline solid that is commonly used as an intermediate in the production of various pharmaceuticals and agrochemicals. It is also utilized in the synthesis of dyes, pigments, and other organic compounds. 4'-Chloro-2-cyanoacetanilide is a versatile compound with a wide range of applications in the chemical industry, and it is important in the production of a variety of products. Due to its potential health hazards, it is essential to handle and use this chemical with appropriate safety measures in place.

Upstream product

• 56290-86-9 3-cyano-2-oxo-propanoic acid ethyl ester 
• 106-47-8 4-chloro-aniline 
• 621-03-4 cyanoacetanilide 
• 36140-83-7 1-cyanoacetyl-3,5-dimethylpyrazole 
• 105-34-0 methyl 2-cyanoacetate 
• 372-09-8 cyanoacetic acid 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 83822-30-4 3-(4-Chloro-phenyl)-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 
• 75690-33-4 N-(4-chlorophenyl)-2-cyano-3-ethoxyacrylamide 
• 438616-84-3 2-amino-N-(4-chlorophenyl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide 

Relevant articles and documents

Synthesis, characterization, and docking studies of novel cyanopyridone analogs with serotonin 5-HT1B receptor agonists

The medications in use for treating migraine are directed either towards inhibiting the characteristic migraine pain or towards preventing it from occurring. In this pursuit, ergotamine and sumatriptan class of 5-HT1B receptor agonists have been proved to be extremely effective. Further research into this field led us to design cyanopyridone derivatives that were synthesized through cyclization of 2-cyano-N-phenylacetamides with malonitrile and 2,3-dihydrobenzo[b][1,4]dioxine-6-carbaldehyde. The synthesized cyanopyridones analogs, when docked with active site of 5-HT1B receptor, showed better binding affinity compared to standard antimigraine medications. Additionally, in silico ADME prediction for drug-likeness and pharmacokinetics revealed that all compounds are safer and can be used as antimigraine medicine. The structure of the synthesized compounds has been elucidated on the basis of spectral analysis.

Nickel-promoted oxidative domino Csp3-H/N-H bond double-isocyanide insertion reaction to construct pyrrolin-2-ones

The first nickel-catalyzed oxidative domino Csp3-H/N-H double isocyanide insertion reaction of acetamides with isocyanides has been developed for the synthesis of pyrrolin-2-one derivatives. A wide range of acetamides bearing various functional groups are compatible with this reaction system by utilizing Ni(acac)2as a catalyst. In this transformation, isocyanide could serve as a C1 connector and insert into the inactive Csp3-H bond, representing an effective way to construct heterocycles.

Development of Novel AKR1C3 Inhibitors as New Potential Treatment for Castration-Resistant Prostate Cancer

Aldo-keto reductase (AKR) 1C3 catalyzes the synthesis of active androgens that promote the progression of prostate cancer. AKR1C3 also contributes to androgen-independent cell proliferation and survival through the metabolism of prostaglandins and reactive aldehydes. Because of its elevation in castration-resistant prostate cancer (CRPC) tissues, AKR1C3 is a promising therapeutic target for CRPC. In this study, we found a novel potent AKR1C3 inhibitor, N-(4-fluorophenyl)-8-hydroxy-2-imino-2H-chromene-3-carboxamide (2d), and synthesized its derivatives with IC50 values of 25-56 nM and >220-fold selectivity over other AKRs (1C1, 1C2, and 1C4). The structural factors for the inhibitory potency were elucidated by crystallographic study of AKR1C3 complexes with 2j and 2l. The inhibitors suppressed proliferation of prostate cancer 22Rv1 and PC3 cells through both androgen-dependent and androgen-independent mechanisms. Additionally, 2j and 2l prevented prostate tumor growth in a xenograft mouse model. Furthermore, the inhibitors significantly augmented apoptotic cell death induced by anti-CRPC drugs (abiraterone or enzalutamide).