117-99-7

Basic information

• Product Name: 2-Hydroxybenzophenone
• Synonyms: (2-Hydroxy-phenyl)-phenylmethanon;(2-hydroxyphenyl)phenyl-methanon;(2-hydroxyphenyl)phenylmethanone;(2-Hydroxy-phenyl)-phenylmethanone;Benzophenone, 2-hydroxy-;benzophenone,2-hydroxy-;methanone,(2-hydroxyphenyl)phenyl-;ortho-Hydroxybenzophenone
• CAS NO: 117-99-7
• Molecular Formula: C₁₃H₁₀O₂
• Molecular Weight: 198.22
• EINECS: 204-226-2
• Product Categories: Aromatic Benzophenones & Derivatives (substituted);API intermediates;Linkers for Solid Phase Synthesis;C13 to C14;Carbonyl Compounds;Ketones
• Mol File: 117-99-7.mol
• Article Data: 95

Chemical Properties

• Melting Point: 37-39 °C(lit.)
• Boiling Point: 171-173 °C12 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Yellow/Crystalline Powder
• Density: 1.1184 (rough estimate)
• Vapor Pressure: 0.000439mmHg at 25°C
• Refractive Index: 1.5954 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: 8.07±0.30(Predicted)
• Water Solubility: insoluble
• BRN: 1638174
• CAS DataBase Reference: 2-Hydroxybenzophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Hydroxybenzophenone(117-99-7)
• EPA Substance Registry System: 2-Hydroxybenzophenone(117-99-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 117-99-7(Hazardous Substances Data)

Usage

Chemical Properties

yellow crystalline powder

Uses

Different sources of media describe the Uses of 117-99-7 differently. You can refer to the following data:
1. UV absorber in plastics.
2. 2-Hydroxybenzophenone was used to quantify the metabolites of unmethylated extracts from the supernatants of Pseudomonas acidovorans cultures grown on 1,1-diphenylethylene.

Application

2-Hydroxybenzophenone was used to quantify the metabolites of unmethylated extracts from the supernatants of Pseudomonas acidovorans cultures grown on 1,1-diphenylethylene.2-Hydroxybenzophenone forms copolymer 2-hydroxy, 3-allyl, 4,4′-dimethoxybenzophenone with methyl methacrylate.It forms photostabilizer compounds with 2,2,6,6-tetramethylpiperidine under phase transfer catalysis conditions.It reacts with 3-aminophenyl boronic acid to form macrocyclic boronates.

Preparation

Preparation by Friedel–Crafts acylation of benzene in the presence of aluminium chloride, ? with 2-hydroxybenzoyl chloride (salicylic acid chloride), (52%), (39%), at temperature <60°; ? with o-anisoyl chloride. Demethylation occurred during the Friedel–Crafts acylation, especially in the presence of ferric chloride at 130–140°; ? with 2-ethoxybenzoyl chloride in a boiling water bath (42%).

Synthesis Reference(s)

Journal of the American Chemical Society, 76, p. 5469, 1954 DOI: 10.1021/ja01650a062The Journal of Organic Chemistry, 32, p. 3844, 1967 DOI: 10.1021/jo01287a027

General Description

2-Hydroxybenzophenone forms copolymer 2-hydroxy, 3-allyl, 4,4′-dimethoxybenzophenone with methyl methacrylate.It forms photostabilizer compounds with 2,2,6,6-tetramethylpiperidine under phase transfer catalysis conditions. It reacts with 3-aminophenyl boronic acid to form macrocyclic boronates.

InChI:InChI=1/C13H10O2/c14-12-9-5-4-8-11(12)13(15)10-6-2-1-3-7-10/h1-9,14H

Upstream product

• 100-52-7 benzaldehyde 
• 15086-27-8 aluminium(III) phenoxide 
• 98-88-4 benzoyl chloride 
• 93-99-2 benzoic acid phenyl ester 
• 98-95-3 nitrobenzene 
• 139-02-6 sodium phenoxide 
• 98-07-7 Benzotrichlorid 
• 65-85-0 benzoic acid 
• 108-95-2 phenol 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 618-32-6 Benzoyl bromide 
• 33719-60-7 <2-(Benzoyloxy)phenyl>phenylketon 
• 13163-77-4 1-phenylhept-6-ene-1,3-dione 
• 93-97-0 benzoic acid anhydride 

Downstream Products

• 2553-04-0 ortho-methoxybenzophenone 
• 810672-90-3 o-butoxybenzophenone 
• 127154-52-3 (2-ethoxyphenyl)(phenyl)methanone 
• 860564-37-0 2-heptyloxy-benzophenone 
• 187093-06-7 2-isobutoxybenzophenone 
• 90-47-1 xanth-9-one 
• 833-50-1 2-phenylbenzo[d]oxazole 
• 26094-08-6 2-hydroxybenzophenone oxime 
• 81118-45-8 o-hydroxythiobenzophenone 
• 59986-61-7 (Z)-o-hydroxybenzophenone oxime 
• 59986-60-6 (E)-o-hydroxybenzophenone oxime 
• 93254-81-0 o-(benzyloxy)benzophenone 
• 39264-92-1 N-(3-Dimethylaminopropyl)-2-hydroxy-diphenylketoimin 
• 62665-68-3 C₁₅H₁₃NO₃ 

Related news

NoteSynthesis, spectroscopic characterization and structural studies of mixed ligand complexes of Sr(II) and Ba(II) with 2-Hydroxybenzophenone (cas 117-99-7) and salicylaldehyde, hydroxyaromatic ketones or β-diketones: Crystal structure of 2-HOC6H4C(O)C6H509/04/2019

Reactions of Sr(II) and Ba(II) chlorides with 2-hydroxybenzophenone and salicylaldehyde, hydroxyaromatic ketones or β-diketones in 1:1:1 molar ratios have resulted in the formation of mixed ligand complexes of the type [MLL′(H2O)2] (M = Sr(II) or Ba(II); HL = 2-hydroxybenzophenone and HL′ = s...detailed

2-Hydroxybenzophenone (cas 117-99-7) UV-absorbers containing 2,2,6,6-tetramethylpiperidine (HALS) group — benzoylation of corresponding phenol derivatives09/02/2019

Phenol derivatives containing 2,2,6,6-tetramethylpiperidine group were successfully benzoylated with both benzoyl chloride in the presence of aluminium chloride and benzotrichloride in aqueous sodium hydroxide solution. The 2-hydroxybenzophenone UV-absorbers bearing light stabilizing fragment —...detailed

2-Hydroxybenzophenone (cas 117-99-7) UV-absorber containing 4,4,5,5-tetramethylimidazolidine fragment08/30/2019

2-Hydroxy-4-[(2,4,4,5,5-pentamethylimidazolidin-2-yl)methoxy]benzophenone (4)-2-hydroxybenzophenone UV-absorber containing 4,4,5,5-tetramethylimidazolidine fragment was obtained in the reaction of 4-(2-oxopropoxy)-2-hydroxybenzophenone (3) with 2,3-diamino-2,3-dimethylbutane (2).detailed

Relevant articles and documents

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Hydroxylation of benzophenone with ammonium phosphomolybdate in the solid state via UV photoactivation

UV photoactivation of a mixture of benzophenone and ammonium phosphomolybdate (APM) in the solid state splits adsorbed moisture, resulting in selectively hydroxylated benzophenone and leaving an electron trapped in green (reduced) solid APM. The Royal Soc

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First direct access to 2-hydroxybenzophenones via nickel-catalyzed cross-coupling of 2-hydroxybenzaldehydes with aryl iodides

An efficient, inexpensive and reusable NiCl2·6H2O/n-Bu4NBr catalytic system is described for the direct C-H arylation of 2-hydroxybenzaldehydes with aryl iodides for the first time.

Rh(III)-catalyzed aldehyde C-H bond functionalization of salicylaldehydes with arylboronic acids

A Rh(III)-catalyzed aldehyde C-H bond functionalization of salicylaldehydes with arylboronic acids has been developed, with features of mild reaction condition and high efficiency. Furthermore, the functionalized 2-hydroxybenzophenone could be subject to divergent synthesis of heterocycles.

PdCl2/DABCO-catalyzed direct arylation of 2-hydroxybenzaldehydes in H2O

In this paper the successful application of DABCO both as base and as ligand for efficient coupling reactions of aryl iodides and bromides with 2-hydroxybenzaldehydes in the presence of catalytic amounts of PdCl2 in water as solvent was introduced.

AN INTRAMOLECULAR OXENOID OXIDATION

Photooxidation of diphenyldiazomethane and 9-diazofluorene leads to the intramolecular oxenoid oxidation products, o-hydroxybenzophenone and 1-hydroxyfluorenone, respectively.

Substituent and Surfactant Effects on the Photochemical Reaction of Some Aryl Benzoates in Micellar Green Environment?

In this study, we carried out preparative and mechanistic studies on the photochemical reaction of a series of p-substituted phenyl benzoates in confined and sustainable micellar environment. The aim of this work is mainly focused to show whether the nature of the surfactant (ionic or nonionic) leads to noticeable selectivity in the photoproduct formation and whether the electronic effects of the substituents affect the chemical yields and the rate of formation of the 5-substituted-2-hydroxybenzophenone derivatives. Application of the Hammett linear free energy relationship (LFER) on the rate of formation of benzophenone derivatives, on the lower energy band of the UV-visible absorption spectra of the aryl benzoates and 5-substituted-2-hydroxybenzophenone derivatives allows a satisfactory quantification of the substituent effects. Furthermore, UV-visible and 2D-NMR (NOESY) spectroscopies have been employed to measure the binding constant Kb and the location of the aryl benzoates within the hydrophobic core of the micelle. Finally, TD-DFT calculations have been carried out to estimate the energies of the absorption bands of p-substituted phenyl benzoates and 5-substituted-2-hydroxybenzophenone derivatives providing good linear correlation with those values measured experimentally.

Aerobic Copper-Catalyzed Salicylaldehydic Cformyl?H Arylations with Arylboronic Acids

We report a challenging copper-catalyzed Cformyl?H arylation of salicylaldehydes with arylboronic acids that involves unique salicylaldehydic copper species that differ from reported salicylaldehydic rhodacycles and palladacycles. This protocol has high chemoselectivity for the Cformyl?H bond compared to the phenolic O?H bond involving copper catalysis under high reaction temperatures. This approach is compatible with a wide range of salicylaldehyde and arylboronic acid substrates, including estrone and carbazole derivatives, which leads to the corresponding arylation products. Mechanistic studies show that the 2-hydroxy group of the salicylaldehyde substrate triggers the formation of salicylaldehydic copper complexes through a CuI/CuII/CuIII catalytic cycle.

Electrophotocatalytic C?H Heterofunctionalization of Arenes

The electrophotocatalytic heterofunctionalization of arenes is described. Using 2,3-dichloro-5,6-dicyanoquinone (DDQ) under a mild electrochemical potential with visible-light irradiation, arenes undergo oxidant-free hydroxylation, alkoxylation, and amination with high chemoselectivity. In addition to batch reactions, an electrophotocatalytic recirculating flow process is demonstrated, enabling the conversion of benzene to phenol on a gram scale.