85-19-8

Basic information

• Product Name: 5-Chloro-2-hydroxybenzophenone
• Synonyms: (5-chloro-2-hydroxyphenyl)phenyl-methanon;2-benzoyl-4-chlorophenol;3-chloro-6-hydroxybenzophenone;5-chloro-2-hydroxy-benzophenon;benzophenone,5-chloro-2-hydroxy-;benzophenone-7;benzophenone-7,5-chloro-2-hydroxybenzophenone;chlorohydroxybenzophenone
• CAS NO: 85-19-8
• Molecular Formula: C₁₃H₉ClO₂
• Molecular Weight: 232.66
• EINECS: 201-592-5
• Product Categories: Aromatic Benzophenones & Derivatives (substituted);Polymer Additives;Polymer Science;Stabilizers
• Mol File: 85-19-8.mol
• Article Data: 26

Chemical Properties

• Melting Point: 96-98 °C(lit.)
• Boiling Point: 355.5 °C at 760 mmHg
• Flash Point: 168.8 °C
• Appearance: /
• Density: 1.307 g/cm³
• Vapor Pressure: 1.52E-05mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 7.49±0.43(Predicted)
• CAS DataBase Reference: 5-Chloro-2-hydroxybenzophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-2-hydroxybenzophenone(85-19-8)
• EPA Substance Registry System: 5-Chloro-2-hydroxybenzophenone(85-19-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 85-19-8(Hazardous Substances Data)

Usage

Preparation

Preparation by Fries rearrangement of p-chlorophenyl benzoate with aluminium chloride, ? without solvent, at 180° for 10 min (85%), at 155–157° for 2 h (90%), at 130– 140° for 1 h (72%) or at 100–150° for 0.5–3 h (68%) ； ? in refluxing chlorobenzene for 4 h (14%).

InChI:InChI=1/C13H9ClO2/c14-10-6-7-12(15)11(8-10)13(16)9-4-2-1-3-5-9/h1-8,15H

Upstream product

• 2005-08-5 4-chlorophenyl benzoate 
• 117-99-7 2-Hydroxybenzophenone 
• 106-48-9 4-chloro-phenol 
• 98-88-4 benzoyl chloride 
• 623-12-1 4-chloromethoxybenzene 
• 92428-34-7 1-Phenyl-3-(4-chlor-phenoxy)-propin-⁽¹⁾ 
• 36637-30-6 O-(4-chlorophenyl)hydroxylamine 
• 1679-18-1 4-Chlorophenylboronic acid 
• 220464-84-6 (p-chloro-N-phenoxy)phthalimide 
• 501-65-5 diphenyl acetylene 
• 635-93-8 5-chlorosalicyclaldehyde 
• 98-80-6 phenylboronic acid 
• 26965-67-3 4-chloro-2-(hydroxy(phenyl)methyl)phenol 
• 108-86-1 bromobenzene 

Downstream Products

• 62714-94-7 C₁₇H₁₆ClNO₃ 
• 141883-75-2 [5-Chloro-2-(cyclohex-2-enyloxy)-phenyl]-phenyl-methanone 
• 62100-48-5 2-(2-Benzoyl-4-chloro-phenoxy)-2-methyl-propionic acid 
• 137711-59-2 ethyl 6-chloro-2-oxo-4-phenyl-2H-chromene-3-carboxylate 
• 38075-43-3 (S)-2-{[1-(5-Chloro-2-hydroxy-phenyl)-1-phenyl-meth-(Z)-ylidene]-amino}-3-methyl-butyric acid 
• 54923-63-6 5-chloro-3-phenylbenzofuran 
• 657-84-1 sodium tosylate 
• 26152-84-1 6-chloro-4-phenyl-2H-chromen-2-one 
• 1374329-57-3 3-acetyl-6-chloro-4-phenyl-2H-chromen-2-one 
• 75270-17-6 2-(2-benzoyl-4-chlorophenoxy)acetyl chloride 

Relevant articles and documents

Water-Tolerant ortho-Acylation of Phenols

A metal-free, water-tolerant, and one-pot process for ortho-acylation of phenols promoted by the iodine source/hydrogen peroxide system has been developed. This transformation undergoes ether formation, iodocyclization, C-C bond cleavage, and oxidative hydrolysis in a one-step manner, which is supported by control experiments.

Nickel-Catalyzed Decarbonyloxidation of 3-Aryl Benzofuran-2(3H)-ones to 2-Hydroxybenzophenones

We have developed a protocol to facilitate the nickel-catalyzed decarbonyloxidation of 3-aryl benzofuran-2(3H)-ones to 2-hydroxybenzophenones under mild conditions, which is an efficient approach for the decarbonyloxidation of lactones in organic synthesis. A diverse range of substrates can undergo C(O)-O/C(O)-C bond cleavage to generate the target products in good yields. These 2-hydroxybenzophenones can be converted into a variety of compounds via reactions such as esterification, cyclization, and reduction.

Practical and efficient synthesis of hydroxyaryl ketones catalyzed by HF@SiO2 under solvent-free condition

A wide variety of hydroxyaryl ketones bearing different motifs was successfully synthesized with good yields and excellent selectivities in the presence of HF@SiO2 as an environmental friendly acid under solvent-free condition. Mild and green reaction conditions and excellent yields (50-91%) make this method an attractive method for the efficient synthesis of hydroxyaryl ketones. Fries rearrangement of phenyl benzoate in the presence of HF@SiO2 led to p-hydroxybenzophenone, while phenyl acetate in the same conditions produced o-hydroxyacetophenone as a single isomer.