107535-73-9

Basic information

• Product Name: 2,3,5,6-TETRAFLUOROBENZOYL CHLORIDE
• Synonyms: 2,3,5,6-TETRAFLUOROBENZOYL CHLORIDE;Benzoyl chloride, 2,3,5,6-tetrafluoro- (9CI);2,3,5,6-Tetrafluorobenzoyl chloride 97%;2,3,5,6-Tetrafluorobenzoylchloride97%;TETRAFLUOROBENZYLCHLORIDE;2,3,5,6-Tetrafluorobenzoyl chloride,98%;2,3,5,6-Tetrafluorboenzoyl Chloride;2,3,5,6-Tetrafluorobenzoic acid chloride
• CAS NO: 107535-73-9
• Molecular Formula: C₇HClF₄O
• Molecular Weight: 212.53
• EINECS: -0
• Product Categories: ACIDHALIDE
• Mol File: 107535-73-9.mol

Chemical Properties

• Boiling Point: 172.1°C at 760 mmHg
• Flash Point: 57.9°C
• Appearance: /
• Density: 1.59
• Vapor Pressure: 1.35mmHg at 25°C
• Refractive Index: 1.4645-1.4665
• Sensitive: Moisture Sensitive
• BRN: 1968840
• CAS DataBase Reference: 2,3,5,6-TETRAFLUOROBENZOYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5,6-TETRAFLUOROBENZOYL CHLORIDE(107535-73-9)
• EPA Substance Registry System: 2,3,5,6-TETRAFLUOROBENZOYL CHLORIDE(107535-73-9)

Safety Data

• Hazard Codes: C
• Statements: 36/37-34
• Safety Statements: 45-36/37/39-26
• RIDADR: 3265
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 107535-73-9(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

InChI:InChI=1/C7HClF4O/c8-7(13)4-5(11)2(9)1-3(10)6(4)12/h1H

Upstream product

• 652-18-6 2,3,5,6-tetrafluorobenzoic acid 
• 327-54-8 1,2,4,5-Tetrafluorobenzene 
• 181183-63-1 2,3,5,6-C₆F₄HCCl₃ 

Downstream Products

• 1117700-42-1 N-(1,2-dimethylpropyl)-2,3,5,6-tetrafluoro-benzamide 
• 1117700-43-2 N-(2-methylcyclohexyl)-2,3,5,6-tetrafluoro-benzamide 
• 123967-73-7 3-Oxo-3-(2,3,5,6-tetrafluoro-phenyl)-propionic acid ethyl ester 
• 1109138-76-2 N-(2-chloroethyl)-2-(2,3,5,6-tetrafluorophenyl)acid amide 

Relevant articles and documents

Carbonic anhydrase inhibitors: Inhibition of the tumor-associated isozyme IX with fluorine-containing sulfonamides. The first subnanomolar CA IX inhibitor discovered

Polyfluorinated CAIs show very good inhibitory properties against different carbonic anhydrase (CA) isozymes, such as CA I, II, and IV, but such compounds have not been tested for their interaction with the transmembrane, tumor-associated isozyme CA IX. Thus, a series of such compounds has been obtained by attaching 2,3,5,6-tetrafluorobenzoyl- and 2,3,5,6- tetrafluorophenylsulfonyl- moieties to aromatic/heterocyclic sulfonamides possessing derivatizable amino moieties. Some of these compounds showed excellent CA IX inhibitory properties and also selectivity ratios favorable to CA IX over CA II, the other physiologically relevant isozyme with high affinity for sulfonamide inhibitors. The first subnanomolar and rather selective CA IX inhibitor has been discovered, as the 2,3,5,6-tetrafluorobenzoyl derivative of metanilamide showed an inhibition constant of 0.8nM against hCA IX, and a selectivity ratio of 26.25 against CA IX over CA II. Several other low nanomolar CA IX inhibitors were detected among the new derivatives reported here. The reported derivatives constitute valuable candidates for the development of novel antitumor therapies based on the selective inhibition of tumor-associated CA isozymes.

Carbonic anhydrase inhibitors: Synthesis and topical intraocular pressure lowering effects of fluorine-containing inhibitors devoid of enhanced reactivity

Polyfluorinated carbonic anhydrase inhibitors (CAIs) show very good inhibitory properties against carbonic anhydrase (CA) and excellent in vivo antiglaucoma properties after topical administration in rabbits. Still, the pentafluorinated compounds reported previously by this group (Scozzafava et al. J. Med. Chem. 2000, 43, 4542-4551) showed high reactivity with thiol groups of cysteine, glutathione, and presumably other proteins containing such moieties, which may lead to severe ocular side effects. Here, we report an approach for obtaining fluorinated CA inhibitors without the undesired enhanced reactivity. Thus, new compounds have been obtained by attaching moieties with reduced reactivity toward aromatic substitution reactions to the molecules of aromatic/heterocyclic sulfonamides possessing derivatizable amino moieties. The employed tails of the 2,3,5,6-tetrafluorobenzoyl, 2,3,5,6-tetrafluophenylsulfonyl, and pentafluorophenylureido types induced excellent CA inhibitory properties in the new reported sulfonamides, mainly against the isozymes involved in aqueous humor secretion, CA II and CA IV, whereas affinity for CA I was lower. Several low-nanomolar CA II inhibitors were detected, which did not react with cysteine or glutathione, in contrast to the corresponding perfluorinated compounds previously reported. These derivatives also showed a potent reduction of the intraocular pressure (IOP) in hypertensive rabbits, amounting to 13-21 mmHg at 1 h postadministration (compared to 5 mmHg obtained with dorzolamide, a clinically used drug), and the decreased IOP was maintained for 4-5 h after the administration. These compounds constitute valuable candidates for obtaining topically acting antiglaucoma CA inhibitors of a new generation, with enhanced efficacy, prolonged duration of action, and reduced side effects.

Synthesis, structural characterization and antimycobacterial evaluation of several halogenated non-nitro benzothiazinones

8-Nitro-1,3-benzothiazin-4-ones (BTZs), with BTZ043 and PBTZ169 as the most advanced compounds, represent a new class of potent antitubercular agents, which irreversibly inhibit decaprenylphosphoryl-β-d-ribose-2′-epimerase (DprE1), an enzyme crucial for c

Synthetic method of transfluthrin intermediate

The invention discloses a synthetic method of a transfluthrin intermediate, and belongs to the technical field of chemical synthesis, the synthetic method is characterized by comprising the following steps: (1) taking 2, 3, 5, 6-tetrafluorobenzene as a raw material, and reacting with carbon tetrachloride to obtain 2, 3, 5, 6-tetrafluorotrichloromethyl benzene; (2) under the action of a composite catalyst, carrying out catalytic hydrolysis on the 2, 3, 5, 6-tetrafluorotrichloromethyl benzene to obtain 2, 3, 5, 6-tetrafluorobenzoyl chloride; (3) under the action of a catalyst, the 2, 3, 5, 6-tetrafluorobenzoyl chloride and hydrogen are subjected to a Rosenmonde reduction reaction, and 2, 3, 5, 6-tetrafluorobenzaldehyde is obtained; (4) carrying out catalytic hydrogenation reaction on the 2, 3, 5, 6-tetrafluorobenzaldehyde and hydrogen to obtain 2, 3, 5, 6-tetrafluorobenzyl alcohol; the method has the advantages of simple steps, high yield of each step and simple reaction; the reaction conditions of each step are mild, and the method has the advantages of low cost, high yield and easily available reaction conditions.

Preparation method of tetrafluorobenzene methanol

Belonging to the technical field of organic synthesis, the invention discloses a preparation method of tetrafluorobenzene methanol. The method includes: reacting tetrafluorobenzoic acid with thionyl chloride to produce tetrafluorobenzoyl chloride, then taking tetrafluorobenzoyl chloride as the raw material, and conducting reduction in water with sodium borohydride activated by an ether solvent toobtain tetrafluorobenzene methanol. According to the invention, the ether solvent and sodium borohydride are subjected to complexing to activate sodium borohydride, water is adopted as the solvent forreduction, the reaction yield is high, the reductant sodium borohydride can complete the reaction at a catalytic amount, and the reaction process is greener and more environmentally friendly.

Sulfonamides compound of target carbonic anhydrase IX and intermediate as well as preparation and application thereof

The invention relates to a sulfonamides compound of target carbonic anhydrase IX and an intermediate as well as preparation and application thereof. The sulfonamides compound of the target carbonic anhydrase IX has a structural formula shown as the descri

Carbonic anhydrase inhibitors. Design of anticonvulsant sulfonamides incorporating indane moieties

A series of aromatic sulfonamides incorporating indane moieties were prepared starting from commercially available 1- and 2-indanamine, and their activity as inhibitors of two carbonic anhydrase (CA, EC 4.2.1.1) isozymes, hCA I and II was studied. The new sulfonamides incorporating acetamido, 4-chloro-benzoyl, valproyl, tetra-, and pentafluorobenzoyl moieties acted as very potent inhibitors of the slow red blood cell isozyme hCA I (Kis in the range of 1.6-8.5 nM), which usually has a lower affinity for such inhibitors, as compared to isozyme II. Some derivatives also showed excellent hCA II inhibitory properties (Kis in the range of 2.3-12 nM), but the anticonvulsant activity of these sulfonamides was rather low as compared to that of other sulfonamide/sulfamate CA inhibitors, such as methazolamide. Furthermore, the 2-amino/acetamido-indane-5-sulfonic acids prepared during this work also showed interesting CA inhibitory properties, with inhibition constants in the range of 43-89 nM against the two isozymes, being among the most potent sulfonic acid CA inhibitors reported so far.

Process for preparing nucleus-halogenated benzoyl chlorides

Ring-halogenated benzoyl chlorides are obtained in a particularly advantageous manner if ring-halogenated benzotrichlorides are reacted with formic acid in the presence of iron salts.