76778-13-7

Basic information

• Product Name: 2-CHLORO-N-(3,4-DIFLUOROPHENYL)ACETAMIDE
• Synonyms: TIMTEC-BB SBB002364;N-CHLOROACETYL-3,4-DIFLUOROANILINE;BUTTPARK 80\07-94;AKOS BBS-00003887;AKOS USSH-4110498;2-CHLORO-N-(3,4-DIFLUOROPHENYL)ACETAMIDE;2-chloro-N-(3,4-difluorophenyl)ethanamide
• CAS NO: 76778-13-7
• Molecular Formula: C₈H₆ClF₂NO
• Molecular Weight: 205.59
• Mol File: 76778-13-7.mol
• Article Data: 14

Chemical Properties

• Melting Point: 110-112
• Boiling Point: 327°C at 760 mmHg
• Flash Point: 151.6°C
• Appearance: /
• Density: 1.444g/cm³
• Vapor Pressure: 0.000207mmHg at 25°C
• Refractive Index: 1.55
• CAS DataBase Reference: 2-CHLORO-N-(3,4-DIFLUOROPHENYL)ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-N-(3,4-DIFLUOROPHENYL)ACETAMIDE(76778-13-7)
• EPA Substance Registry System: 2-CHLORO-N-(3,4-DIFLUOROPHENYL)ACETAMIDE(76778-13-7)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 76778-13-7(Hazardous Substances Data)

Usage

General Description

2-CHLORO-N-(3,4-DIFLUOROPHENYL)ACETAMIDE is a chemical compound that belongs to the class of acetamides. It is characterized by the presence of a chloro group and a difluorophenyl group in its structure. 2-CHLORO-N-(3,4-DIFLUOROPHENYL)ACETAMIDE has potential applications in pharmaceutical and medicinal chemistry, where it may be used as an intermediate in the synthesis of various drugs and pharmaceuticals. Additionally, it may also have uses in research and development as a building block for the creation of new chemical compounds. Its structure and properties make it of interest to scientists and researchers looking to develop new drugs or materials.

InChI:InChI=1/C8H6ClF2NO/c9-4-8(13)12-5-1-2-6(10)7(11)3-5/h1-3H,4H2,(H,12,13)

Upstream product

• 79-04-9 chloroacetyl chloride 
• 3863-11-4 3,4-difluoroaniline 

Downstream Products

• 71294-07-0 5,6-difluoro-1,3-dihydro-indol-2-one 
• 1044508-19-1 2-[(1R,3S,5S)-4'-(4-chlorophenyl)-5'-oxospiro[bicyclo[3.1.0]hexane-3,2'-imidazol]-1'(5'H)-yl]-N-(3,4-difluorophenyl)acetamide 
• 1044506-95-7 1,1-dimethylethyl 2-(4-chlorophenyl)-4-{2-[(3,4-difluorophenyl)amino]-2-oxoethyl}-3-oxo-1,4,8-triazaspiro[4.5]dec-1-ene-8-carboxylate 
• 1044506-97-9 1,1-dimethylethyl 2-(4-chlorophenyl)-4-{2-[(3,4-difluorophenyl)amino]-2-oxoethyl}-3-oxo-1,4,7-triazaspiro[4.5]dec-1-ene-7-carboxylate 
• 1182141-72-5 N-(3, 4-difluorophenyl)-2-(4-formylphenoxy)acetamide 
• 1266715-55-2 (Z)-N-(3,4-difluorophenyl)-2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)acetamide 
• 1421507-31-4 (E)-3-benzylidene-5,6-difluoro-1,3-dihydro-indol-2-one 
• 1421507-34-7 (E)-5,6-difluoro-3-(2-fluoro-benzylidene)-1,3-dihydro-indol-2-one 
• 1421507-37-0 (E)-5,6-difluoro-3-(3-fluorobenzylidene)-1,3-dihydro-indol-2-one 
• 1421507-38-1 (E)-5,6-difluoro-3-(4-fluoro-benzylidene)-1,3-dihydro-indol-2-one 
• 1421507-39-2 (E)-5,6-difluoro-3-(2-trifluoromethyl-benzylidene)-1,3-dihydro-indol-2-one 
• 1421507-44-9 (E)-5,6-difluoro-3-(3-trifluoromethyl-benzylidene)-1,3-dihydro-indol-2-one 
• 1421507-45-0 (E)-5,6-difluoro-3-(4-(trifluoromethyl)benzylidene)-1,3-dihydro-indol-2-one 
• 1421507-46-1 (E)-5,6-difluoro-3-(3-trifluoromethoxyl-benzylidene)-1,3-dihydro-indol-2-one 

Relevant articles and documents

Synthesis and Biological Evaluation of Dithiobisacetamides as Novel Urease Inhibitors

Thirty-eight disulfides containing N-arylacetamide were designed and synthesized in an effort to develop novel urease inhibitors. Biological evaluation revealed that some of the synthetic compounds exhibited strong inhibitory potency against both cell-free urease and urease in intact cell with low cytotoxicity to mammalian cells even at concentration up to 250 μM. Of note, 2,2′-dithiobis(N-(2-fluorophenyl)acetamide) (d7), 2,2′-dithiobis(N-(3,5-difluorophenyl)acetamide) (d24), and 2,2′-dithiobis(N-(3-fluorophenyl)acetamide) (d8) were here identified as the most active inhibitors with IC50 of 0.074, 0.44, and 0.81 μM, showing 32- to 355-fold higher potency than the positive control acetohydroxamic acid. These disulfides were confirmed to bind urease without covalent modification of the cysteine residue and to inhibit urease reversibly with a mixed inhibition mechanism. They also showed very good anti-Helicobacter pylori activities with d8 showing a comparable potency to the clinical used drug amoxicillin. The impressive in vitro biological profile indicated their immense potential as therapeutic agents to tackle H. pylori caused infections.

N'-Alkylaminosulfonyl Analogues of 6-Fluorobenzylideneindolinones with Desirable Physicochemical Profiles and Potent Growth Inhibitory Activities on Hepatocellular Carcinoma

The benzylideneindolinone 6-chloro-3-(3′-trifluoromethylbenzylidene)-1,3-dihydroindol-2-one (4) was reported to exhibit potent and selective growth inhibitory effects on hepatocellular carcinoma (HCC). Corroborative evidence supported multi-receptor tyrosine kinase (RTK) inhibition as a possible mode of action. However, the poor physicochemical properties of 4 limited its furtherance as a lead compound. In this study, the modification of 4 was investigated with the aim of improving its potency and physicochemical profile. The 6-fluorobenzylideneindolinone 3-12 bearing a 3′-N-propylaminosulfonyl substituent was found to be a promising substitute. Compound 3-12 [6-fluoro-3-(3′-N-propylaminosulfonylbenzylidene)-1,3-dihydroindol-2-one] was found to be tenfold more soluble than 4 and to have sub-micromolar growth inhibitory activities on HCC cells. It is apoptogenic and inhibits the phosphorylation of several RTKs in HuH7, of which the inhibition of FGFR4 and HER3 are prominent. Compound 3-12 decreased the tumor load in a physiologically relevant orthotopic HCC xenograft murine model. Structure-activity relationships support pivotal roles for the fluoro and N′-propylaminosulfonyl moieties in enhancing cell-based activity and moderating the physicochemical profile (solubility, permeability) of 3-12.

Synthesis and biological evaluation of novel 5-benzylidenethiazolidine-2,4- dione derivatives for the treatment of inflammatory diseases

Twenty-two compounds based on thiazolidine-2,4-dione moiety were synthesized and evaluated for the inhibitory potency on the production of nitric oxide (NO), inducible nitric oxide synthase (iNOS) activity, and the generation of prostaglandin E2 (PEG2). (Z)-N-(3-Chlorophenyl)-2-(4- ((2,4-dioxothiazolidin-5-ylidene) methyl) phenoxy) acetamide (3I), superior to the commercial anti-inflammatory drug indomethacin, significantly inhibited iNOS activity (IC50 = 8.66 μM), iNOS-mediated NO, and cyclooxygenase (COX)-2-derived PGE2 production (IC50 = 4.16 and 23.55 μM, respectively) on lipopolysaccharide (LPS)-induced RAW 264.7 cells. Docking study revealed that 3I was perfectly docking into the active site of murine iNOS and suppressed the expression of iNOS protein as evidenced by Western blot analysis. At the dose of 50 mg/kg, oral administration of 3I possessed protective properties in both carrageenan-induced paw edema and adjuvant-induced arthritis rat models.