18355-73-2

Basic information

• Product Name: 2,3-Difluorobenzoyl chloride
• Synonyms: 2,3-DIFLUOROBENZOYL CHLORIDE;2,3-Difluorobenzoyl chloride 98%;2,3-Difluorobenzoylchloride98%;3-(Chlorocarbonyl)-1,2-difluorobenzene;2,3-Difluorobenzoyl chloride, 98% 1GR
• CAS NO: 18355-73-2
• Molecular Formula: C₇H₃ClF₂O
• Molecular Weight: 176.55
• Product Categories: Miscellaneous;Acid Halides;Carbonyl Compounds;Organic Building Blocks;Fluorine series
• Mol File: 18355-73-2.mol

Chemical Properties

• Boiling Point: 85-87 °C14 mm Hg(lit.)
• Flash Point: 195 °F
• Appearance: Clear colorless liquid
• Density: 1.423 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.346mmHg at 25°C
• Refractive Index: n20/D 1.5143(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive: Moisture Sensitive
• BRN: 2965225
• CAS DataBase Reference: 2,3-Difluorobenzoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Difluorobenzoyl chloride(18355-73-2)
• EPA Substance Registry System: 2,3-Difluorobenzoyl chloride(18355-73-2)

Safety Data

• Hazard Codes: C
• Statements: 34-36/37
• Safety Statements: 23-26-27-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 18355-73-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Difluorobenzoyl chloride is used as a key intermediate in the synthesis of N-(6-chloro-5-fluoro-1,3-benzothiazol-2-yl)-2,3-difluorobenzamide, a compound with potential pharmaceutical applications. Its unique structure and reactivity contribute to the development of new drugs with improved therapeutic properties.
Used in Organic Synthesis:
2,3

InChI:InChI=1/C7H3ClF2O/c8-7(11)4-2-1-3-5(9)6(4)10/h1-3H

Upstream product

• 4519-39-5 2,3-difluorobenzoic acid 

Downstream Products

• 16895-58-2 2H-1-benzothiopyran-3(4H)-one 
• 146173-66-2 4-(2,4-difluorobenzoyl)thiochroman-3-one 
• 219636-59-6 2,3-Difluoro-benzoic acid 2,6-di-tert-butyl-4-methoxy-phenyl ester 
• 860016-97-3 (2,3-difluorophenyl)-(thiophen-2-yl)methanone 
• 908336-75-4 2,3-difluoro-N-(4-chloro-2-hydroxyphenyl)-benzamide 
• 908336-72-1 2,3-difluoro-N-(5-chloro-2-hydroxyphenyl)-benzamide 
• 1002093-71-1 2,3-difluorobenzoyl cyanide 
• 902524-15-6 3-(2',3'-difluorophenyl)isocoumarin 
• 902524-19-0 2'-(2'',3''-difluorobenzoylmethyl)benzoic acid 
• 1011493-54-1 2-[2'-hydroxy-2'-(2'',3''-difluorophenyl)ethyl]benzoic acid 

Relevant articles and documents

Novel quinazoline derivatives bearing various 6-benzamide moieties as highly selective and potent EGFR inhibitors

A series of novel quinazoline derivatives bearing various C-6 benzamide substituents were synthesized and evaluated as EGFR inhibitors, and most showed significant inhibitory potency against EGFR kinase. In particular, compound 6g possessed potent inhibitory activity against EGFR wild-type (IC50 = 5 nM), and strong antiproliferative activity against HCC827 and Ba/F3 (L858R) cell lines. Kinase profiling against a panel of 365 kinases showed that 6g was highly selective for EGFR. Furthermore, 6g showed desirable properties in assays of liver microsome metabolic stability and cytochromes P450 inhibition and preliminary pharmacokinetic study. The overall attractive profile of 6g made it an interesting compound for further development.

SPIROPIPERIDINE COMPOUNDS AS ORL-1 RECEPTOR ANTAGONISTS

An ORL-1 receptor antagonist of the formula: its uses, and methods for its preparation are described. ORL-1 antagonists are deemed to be useful in the treatment of depression and/or the treatment of overweight, obesity, and/or weight maintenance post treatment for overweight or obesity. Certain compounds have also demonstrated through animal models that the compounds of the present invention are useful for the treatment of migraines.

N -pyridyl and pyrimidine benzamides as KCNQ2/Q3 potassium channel openers for the treatment of epilepsy

A series of N-pyridyl benzamide KCNQ2/Q3 potassium channel openers were identified and found to be active in animal models of epilepsy and pain. The best compound 12 [ICA-027243, N-(6-chloro-pyridin-3-yl)-3,4-difluoro-benzamide] has an EC50 of 0.38 μM and is selective for KCNQ2/Q3 channels. This compound was active in several rodent models of epilepsy and pain but upon repeated dosing had a number of unacceptable toxicities that prevented further development. On the basis of the structure-activity relationships developed around 12, a second compound, 51, [N-(2-chloro-pyrimidin-5-yl)-3,4-difluoro- benzamide, ICA-069673], was prepared and advanced into a phase 1 clinical study. Herein, we describe the structure-activity relationships that led to the identification of compound 12 and to the corresponding pyrimidine 51.

Synthesis and anti-inflammatory activity of fluorinated isocoumarins and 3,4-dihydroisocoumarins

The synthesis of several fluorinated isocoumarins and 3,4-dihydroisocoumarins are described. The structures of the synthesized compounds were confirmed by spectral and elemental analysis. All synthesized compounds were evaluated for their anti-inflammatory and antioxidant activity. These compounds were found to present antioxidant and anti-inflammatory activities. A few of them were found to be significantly active in vivo against ear edema in mice produced by 12-O-tetradecanoylphorbol-13-acetate (TPA) and also good radical scavengers.

Characterization of the histamine H4 receptor binding site. Part 1. Synthesis and pharmacological evaluation of dibenzodiazepine derivatives

A series of dibenzodiazepine derivatives was synthesized to probe the binding site of the recently discovered histamine H4 receptor (H 4R). Optimization of the lead structure clozapine (2) resulted in (E)-7-chloro-11(4-methylpiperazin-1-yl)dibenzo[b,f][1,4]oxazepine (7j), a potent H4R agonist (H4R, pK, = 7.6). Pharmacological data suggests that the series of nonimidazole compounds can be used to describe the orthosteric binding site of the H4R because both 2 and 7j displace [3H]histamine in a competitive manner. Furthermore, it is demonstrated that the effects of 7j are competitively antagonized by the selective H4R antagonist JNJ 7777120 (1), indicating considerable overlap of their binding sites. On the basis of the derived structure-activity relationships and additional pharmacological results, a pharmacophore model was constructed, which will be the premise for the design of novel H4R ligands.

Accelerating effect of meta substituents in the ester-mediated nucleophilic aromatic substitution reaction

The ester-mediated nucleophilic aromatic substitution (SNAr) reaction of 2-methoxybenzoic ester 1 with Grignard reagents 11 is greatly accelerated by introduction of a methoxy or halo substituent at the 3-position of the benzoate ring (7-10). The substituent effects of these groups at the 3-position are compared with those at the 5-position to suggest that the activation mechanism of the methoxy substituent is different from that of the halo substituent; the ligating ability of the 3-methoxy group plays a crucial role in enhancing the reactivity of the 2-methoxy moiety, while the electron-withdrawing ability is more important in the case of the halo groups. It has also been found that introduction of an additional methoxy substituent at the meta-position (33, 34) enables the SNAr methoxy-displacement reaction even at the para-position to the ester activator. The accelerating effect of the 3-bromo substituent is advantageously utilized for regioselective allylation of 3-bromo-2,6-dimethoxybenzoic ester 55 at the 2-position to provide an easy access to a multisubstituted naphthol 59, which is a key compound for the syntheses of michellamines A-C and the related naphthylisoquinoline alkaloids.