4'-Chloro-5-fluoro-2-hydroxybenzophenone

Base Information

• Chemical Name: 4'-Chloro-5-fluoro-2-hydroxybenzophenone
• CAS No.: 62433-26-5
• Molecular Formula: C13H8 Cl F O2
• Molecular Weight: 250.657
• Hs Code.: 2914700090
• European Community (EC) Number: 263-539-2
• DSSTox Substance ID: DTXSID40211476
• Nikkaji Number: J227.882K
• Wikidata: Q72450786
• Mol file: 62433-26-5.mol

Synonyms:62433-26-5;(4-Chlorophenyl)(5-fluoro-2-hydroxyphenyl)methanone;4'-Chloro-5-fluoro-2-hydroxybenzophenone;(4-chlorophenyl)-(5-fluoro-2-hydroxyphenyl)methanone;EINECS 263-539-2;Methanone, (4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)-;4-Chloro-5'-fluoro-2'-hydroxybenzophenone;2-(4-chlorobenzoyl)-4-fluorophenol;SCHEMBL143515;EthylN-Cbz-2-piperidineacetate;DTXSID40211476;MFCD00040948;AKOS015913537;DS-4656;2-hydroxy-5-fluoro-4'-chloro-benzophenone;4'-chloro-5-fluoro-2-hydroxy-benzophenone;4/'-Chloro-5-fluoro-2-hydroxybenzophenone;SL-79-182;C3338;CS-0157560;FT-0618114;4'-Chloro-5-fluoro-2-hydroxybenzophenone, 96%;A833767

Chemical Property of 4'-Chloro-5-fluoro-2-hydroxybenzophenone

Chemical Property:

• Melting Point: 65-69 °C(lit.)
• Boiling Point: 145-152/5mm
• Flash Point: 177.2ºC
• PSA: 37.30000
• Density: 1.376g/cm3
• LogP: 3.41570
• Storage Temp.: 2-8°C
• Water Solubility.: 8.999mg/L(37 oC)
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 250.0196853
• Heavy Atom Count: 17
• Complexity: 277

Purity/Quality:

97% ^*data from raw suppliers

4''-Chloro-5-fluoro-2-hydroxybenzophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)C2=C(C=CC(=C2)F)O)Cl
• 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.

Technology Process of 4'-Chloro-5-fluoro-2-hydroxybenzophenone

There total 8 articles about 4'-Chloro-5-fluoro-2-hydroxybenzophenone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

4-Cyanochlorobenzene (623-03-0) + O-4-fluorophenyl N,N-diethylcarbamate (146328-82-7) → (4-chlorophenyl)-(5-fluoro-2-hydroxyphenyl)methanone (62433-26-5)

Guidance literature:

O-4-fluorophenyl N,N-diethylcarbamate; With sec.-butyllithium; In tetrahydrofuran; cyclohexane; at -78 - -65 ℃; for 1.58333h; Inert atmosphere;

4-Cyanochlorobenzene; In tetrahydrofuran; cyclohexane; at -65 - 20 ℃; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; cyclohexane; water; Inert atmosphere;

DOI:10.1021/acs.orglett.8b00782

Reference yield: 80.0%

3-((4-chlorophenyl)-(3-fluoro-6-hydroxyphenyl)methylene)-1,1-diethylurea → (4-chlorophenyl)-(5-fluoro-2-hydroxyphenyl)methanone (62433-26-5)

Guidance literature:

With hydrogenchloride; In water; for 16h; Inert atmosphere;

DOI:10.1021/acs.joc.0c01732

Reference yield: 65.0%

4-chlorobenzoic acid 4-fluorophenyl ester (29558-88-1) → (4-chlorophenyl)-(5-fluoro-2-hydroxyphenyl)methanone (62433-26-5)

Guidance literature:

With aluminium trichloride; at 200 ℃; for 0.25h;

DOI:10.1021/jm00180a029

upstream raw materials:

4-chlorobenzoic acid 4-fluorophenyl ester

4-Fluorophenol

4-chloro-benzoyl chloride

4-Cyanochlorobenzene

Downstream raw materials:

progabide

3-(4'-chlorophenyl)-5-fluorobenzofuran

C₁₆H₁₂ClFO₃

C₁₉H₁₈ClFO₃