6579-27-7

Basic information

• Product Name: 2,6-DICHLORO-N-HYDROXYBENZENECARBOXIMIDOYL CHLORIDE
• Synonyms: 2,6-DICHLORO-N-HYDROXYBENZENECARBOXIMIDOYL CHLORIDE;ALPHA,2,6-TRICHLOROBENZALDOXIME, TECH.;2,6-DICHLORO-N-HYDROXYBENZENECARBOXIMIDOYL CHLOR;2,6-Dichloro-n-hydroxybenzenecarboximidoyl chlorid;2,6-Dichloro-N-hydroxybenzenecarboximidoyl chloride , Tech.;alpha-Chloro-2,6-dichlorobenzaldoxime;2,6-Dichlorobenzenehydroximic acid chloride;2,6-Dichlorobenzohydroxamoyl chloride
• CAS NO: 6579-27-7
• Molecular Formula: C₇H₄Cl₃NO
• Molecular Weight: 224.47
• Mol File: 6579-27-7.mol
• Article Data: 62

Chemical Properties

• Melting Point: 85 °C
• Boiling Point: 349.187 °C at 760 mmHg
• Flash Point: 164.983 °C
• Appearance: /
• Density: 1.53
• Vapor Pressure: 1.79E-05mmHg at 25°C
• Refractive Index: 1.597
• PKA: 9.77±0.70(Predicted)
• CAS DataBase Reference: 2,6-DICHLORO-N-HYDROXYBENZENECARBOXIMIDOYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DICHLORO-N-HYDROXYBENZENECARBOXIMIDOYL CHLORIDE(6579-27-7)
• EPA Substance Registry System: 2,6-DICHLORO-N-HYDROXYBENZENECARBOXIMIDOYL CHLORIDE(6579-27-7)

Safety Data

• Hazard Codes: C
• Hazardous Substances Data: 6579-27-7(Hazardous Substances Data)

Usage

General Description

2,6-Dichloro-n-hydroxybenzenecarboximidoyl chloride, also known as dihydroxydichlorobenzimidoyl chloride, is a chemical compound with the molecular formula C7H4Cl2N2O2. It is a chlorinated derivative of benzenecarboximidoyl chloride and is used in the synthesis of various pharmaceuticals and other organic compounds. 2,6-Dichloro-n-hydroxybenzenecarboximidoyl chloride is a white to light brown powder with a molecular weight of 224.03 g/mol. 2,6-Dichloro-n-hydroxybenzenecarboximidoyl chloride is also used as an intermediate in the production of dyes and pigments, as well as in the manufacture of some specialty chemicals. It is important to handle this compound with caution, as it can be harmful if swallowed, inhaled, or absorbed through the skin, and it may cause irritation to the respiratory system, skin, and eyes.

InChI:InChI=1/C7H4Cl3NO/c8-4-2-1-3-5(9)6(4)7(10)11-12/h1-3,12H

Upstream product

• 3714-77-0 2,6-dichlorobenzaldoxime 
• 25185-95-9 2,6-dichlorobenzaldoxime 
• 6575-28-6 (1E)-2,6-dichlorobenzaldehyde oxime 
• 83-38-5 2,6-dichlorobenzaldehyde 

Downstream Products

• 129144-36-1 3-(2,6-Dichloro-phenyl)-5-propionyl-isoxazole-4-carboxylic acid methyl ester 
• 129144-34-9 3-(2,6-Dichloro-phenyl)-4-propionyl-isoxazole-5-carboxylic acid methyl ester 
• 122247-14-7 4-(4-Chloro-phenyl)-3-(2,6-dichloro-phenyl)-5-trifluoromethyl-isoxazole 
• 122247-07-8 5-(4-Chloro-phenyl)-3-(2,6-dichloro-phenyl)-4-trifluoromethyl-isoxazole 
• 122247-15-8 3-(2,6-Dichloro-phenyl)-4-(4-methoxy-phenyl)-5-trifluoromethyl-isoxazole 
• 122247-08-9 3-(2,6-Dichloro-phenyl)-5-(4-methoxy-phenyl)-4-trifluoromethyl-isoxazole 
• 122247-17-0 4-[3-(2,6-Dichloro-phenyl)-5-trifluoromethyl-isoxazol-4-yl]-phenylamine 
• 122247-10-3 4-[3-(2,6-Dichloro-phenyl)-4-trifluoromethyl-isoxazol-5-yl]-phenylamine 
• 122247-16-9 4-(2-Chloro-phenyl)-3-(2,6-dichloro-phenyl)-5-trifluoromethyl-isoxazole 
• 122247-09-0 5-(2-Chloro-phenyl)-3-(2,6-dichloro-phenyl)-4-trifluoromethyl-isoxazole 
• 144104-75-6 1,3-di-(p-nitrobenzyl)-5-(2,6-dichlorobenzoyl)uracil oxime 
• 6590-95-0 2,6-dichlorophenylisothiocyanate 
• 135073-84-6 3-(2,6-Dichloro-phenyl)-5,7-dimethyl-7,7a-dihydro-3aH-isoxazolo[5,4-d]pyrimidine-4,6-dione 
• 135073-83-5 1,3-Dimethyl-5-(2,6-dichlorobenzoyl)uracil oxime 

Relevant articles and documents

Discovery of novel ketoxime ether derivatives with potent FXR agonistic activity, oral effectiveness and high liver/blood ratio

The farnesoid X receptor (FXR) is a promising therapeutic target for nonalcoholic steatohepatitis (NASH) and other bile acid related diseases because it plays a critical role in fibrosis, inflammation and bile acid homeostasis. Obeticholic acid (OCA), a FXR agonist which was synthesized from chenodeoxycholic acid, showed desirable curative effects in clinical trials. However, the pruritus which was the main side effect of OCA limited its further applications in NASH. Although pruritus was also observed in the clinical trials of non-steroidal FXR agonists, the proportion of patients with pruritus was much smaller than that of OCA. Thus, we decided to develop non-steroidal FXR agonists and discovered a series of novel FXR agonists which were synthesized from GW4064 by replacing the stilbene group with ketoxime ether. Encouragingly, in the following biological tests, our target compounds 13j and 13z not only showed potent FXR agonistic activities in vitro, but also effectively promoted the expression of target genes in vivo. More importantly, in the pharmacokinetic experiments, compounds 13j and 13z displayed high liver/blood ratio characteristics which were helpful to reduce the potential side effects which were caused by prolonged systemic activation of FXR. In summary, our compounds were good choices for the development of non-steroidal FXR agonists and were deserved further investigation.

Discovery of BMS-986318, a Potent Nonbile Acid FXR Agonist for the Treatment of Nonalcoholic Steatohepatitis

Herein we report the discovery and preclinical biological evaluation of 6-(2-(5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)isoxazol-4-yl)-7-azaspiro[3.5]non-1-en-7-yl)-4-(trifluoromethyl)quinoline-2-carboxylic acid, compound 1 (BMS-986318), a nonbile acid farnesoid X receptor (FXR) agonist. Compound 1 exhibits potent in vitro and in vivo activation of FXR, has a suitable ADME profile, and demonstrates efficacy in the mouse bile duct ligation model of liver cholestasis and fibrosis. The overall profile of compound 1 supports its continued evaluation.

BENZISOXAZOLE COMPOUND

The present invention provides a compound, a salt thereof, or a prodrug thereof as a compound effective for preventing and/or treating fibrosis, the compound being represented by formula (1) (wherein A is an optionally substituted benzene ring; B is optionally substituted aryl or optionally substituted heteroaryl; X is an oxygen atom or a sulfur atom; Y is a nitrogen atom or a carbon atom; ------ of -----Y is a single or double bond when Y is a carbon atom, or ------ of -----Y is a single bond when Y is a nitrogen atom; each R1 independently represents lower alkyl, or two R1s may be bound to each other to form a spiro ring or a crosslinked structure, or two R1s may be bound to each other to form a saturated fused heterocycle together with nitrogen and carbon atoms constituting a ring containing Y; p is 0, 1, or 2; or (R1)p is oxo) .