62433-26-5

Basic information

• Product Name: 4'-CHLORO-5-FLUORO-2-HYDROXYBENZOPHENONE
• Synonyms: METHANONE, (4-CHLOROPHENYL)(5-FLUORO-2-HYDROXYPHENYL)-;4'-CHLORO-5-FLUORO-2-HYDROXYBENZOPHENONE;4-CHLORO-5'-FLUORO-2'-HYDROXYBENZOPHENONE;4'-CHLORO-5-FLUORO-2-HYDROXYBENZOPHENON&;4'-Chloro-5-fluoro-2-hydroxybenzophenone97%;(4-Chlorophenyl)(5-fluoro-2-hydroxyphenyl) ketone;2-Hydroxy-4'-chloro-5-fluorobenzophenone;SL-79-182
• CAS NO: 62433-26-5
• Molecular Formula: C₁₃H₈ClFO₂
• Molecular Weight: 250.65
• EINECS: 263-539-2
• Product Categories: C13 to C14;Carbonyl Compounds;Ketones
• Mol File: 62433-26-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 65-69 °C(lit.)
• Boiling Point: 145-152/5mm
• Flash Point: 177℃
• Appearance: /
• Density: 1.376
• Storage Temp.: 2-8°C
• Water Solubility: 8.999mg/L(37 oC)
• CAS DataBase Reference: 4'-CHLORO-5-FLUORO-2-HYDROXYBENZOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-CHLORO-5-FLUORO-2-HYDROXYBENZOPHENONE(62433-26-5)
• EPA Substance Registry System: 4'-CHLORO-5-FLUORO-2-HYDROXYBENZOPHENONE(62433-26-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 62433-26-5(Hazardous Substances Data)

Usage

Uses

4''-Chloro-5-fluoro-2-hydroxybenzophenone is a metabolite of Progabide (P755350) which is a gamma-aminobutyric acid (GABA) antagonist with antiepileptic activity. 4''-Chloro-5-fluoro-2-hydroxybenzophenone is also used as a reagent in the synthesis of a series of novel dihydrobenzofuranols which displayed antibacterial activity comparable to bacitracin, ciprofloxacin and gentamicin.

Preparation

Preparation by Fries rearrangement of p-fluorophenyl p-chlorobenzoate, ? with titanium tetrachloride at 150° for 18 h (81%); ? with aluminium chloride, at 130° for 2 h (98%) or at 200° for 5 min or for 15 min (65%).

Upstream product

• 146328-82-7 O-4-fluorophenyl N,N-diethylcarbamate 
• 371-41-5 4-Fluorophenol 
• 623-03-0 4-Cyanochlorobenzene 
• 122-01-0 4-chloro-benzoyl chloride 
• 29558-88-1 4-chlorobenzoic acid 4-fluorophenyl ester 

Downstream Products

• 62665-97-8 4-{[1-(4-Chloro-phenyl)-1-(5-fluoro-2-hydroxy-phenyl)-meth-(Z)-ylidene]-amino}-butyric acid 
• 90656-51-2 progabide 
• 136136-02-2 2-<(2-hydroxypropylimino)(4-chlorophenyl)methyl>-4-fluorophenol 
• 1034192-10-3 3-{[(1E)-(4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylene]amino}propane-1-sulfonamide 
• 1379805-05-6 3-(4'-chlorophenyl)-5-fluorobenzofuran 
• 1322705-95-2 C₁₆H₁₂ClFO₃ 
• 1322705-99-6 C₁₉H₁₈ClFO₃ 
• 1322705-97-4 C₁₇H₁₄ClFO₃ 
• 1322706-01-3 C₂₁H₁₄ClFO₃ 
• 1322706-07-9 C₁₅H₈ClFO₂ 
• 1322706-16-0 C₂₁H₁₂ClFO₂ 
• 1322706-15-9 C₁₉H₁₆ClFO₂ 
• 1322706-14-8 C₁₇H₁₂ClFO₂ 
• 1322706-13-7 C₁₆H₁₀ClFO₂ 

Relevant articles and documents

Experimental and computational study of the 1,5-o → n carbamoyl snieckus-fries-type rearrangement

The reactions of o-lithiated O-aryl N,N-diethylcarbamates with different C-N multiple bond electrophiles have been thoroughly studied. A 1,5-O → N carbamoyl shift, a new variation of the anionic Fries-type rearrangement, takes place when nitriles, imines, or alkylcarbodiimides are employed. In these cases, the carbamoyl group plays a dual role as a directing group, building up a variety of functional groups through the 1,5-O → N carbamoyl migration. On the other hand, the use of iso(thio)cyanates and arylcarbodiimides led to non-rearranged o-functionalized Oarylcarbamates. This reactivity was further computationally explored, and the governing factor could be traced back to the relative basicity of the alternative products (migrated vs nonmigrated substrates). This exploration also provided interesting insights about the degree of complexation of the lithium cations onto these substrates. A new access to useful 2-hydroxybenzophenone derivatives has also been developed.

1,5-O → N Carbamoyl Snieckus-Fries-Type Rearrangement

The reaction of o-lithiated O-aryl N,N-diethylcarbamates with (hetero)aromatic nitriles gives rise to functionalized salicylidene urea derivatives in high yields through a new 1,5-O → N carbamoyl migration. This Snieckus-Fries-type rearrangement nicely complements previously known O → C and O → O related shifts. In addition, when dimethylmalononitrile is used as the electrophilic partner, the carbamoyl shift is preferred over the expected transnitrilation reaction.

New anticonvulsants: Schiff bases of γ-aminobutyric acid and γ-aminobutyramide

Schiff bases of γ-aminobutyric acid (γAbu) and γ-aminobutyramide (γAbuNH2) were prepared and tested for anticonvulsant and γAbu mimetic activity. 4-[[(4-Chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylene]amino]butanoic acid monosodium salt (4) and 4-[[(4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylene]amino]butanamide (5) blocked bicuculline-induced lethality and convulsions and displaced [3H]γAbu from its membrane binding sites. In the rat dorsal root sensory ganglion, compound 4 exhibited γAbu agonist properties. Compounds 4 and 5 are thus anticonvulsants and directly acting γAbu mimetics.