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2-Hydroxybenzophenone is a yellow crystalline powder that is a type of benzophenone derivative. It is known for its ability to form copolymers and photostabilizer compounds, as well as its reactivity with other chemical compounds.

117-99-7

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117-99-7 Usage

Uses

Used in Plastics Industry:
2-Hydroxybenzophenone is used as a UV absorber in plastics to protect them from the harmful effects of ultraviolet radiation, thereby enhancing their durability and longevity.
Used in Chemical Research:
2-Hydroxybenzophenone is used to quantify the metabolites of unmethylated extracts from the supernatants of Pseudomonas acidovorans cultures grown on 1,1-diphenylethylene. This application is crucial for studying the metabolic processes and interactions of these bacteria with their environment.
Used in Polymer Synthesis:
2-Hydroxybenzophenone is used as a monomer to form copolymers, such as 2-hydroxy, 3-allyl, 4,4′-dimethoxybenzophenone, with methyl methacrylate. These copolymers have potential applications in various industries, including coatings, adhesives, and composite materials.
Used in Photostabilizer Production:
2-Hydroxybenzophenone is used in the formation of photostabilizer compounds with 2,2,6,6-tetramethylpiperidine under phase transfer catalysis conditions. These photostabilizers are important for protecting materials from the degrading effects of light exposure.
Used in Organic Synthesis:
2-Hydroxybenzophenone reacts with 3-aminophenyl boronic acid to form macrocyclic boronates, which have potential applications in various fields, such as pharmaceuticals, materials science, and supramolecular chemistry.

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

Check Digit Verification of cas no

The CAS Registry Mumber 117-99-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 7 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 117-99:
(5*1)+(4*1)+(3*7)+(2*9)+(1*9)=57
57 % 10 = 7
So 117-99-7 is a valid CAS Registry Number.
InChI:InChI=1/C13H10O2/c14-12-9-5-4-8-11(12)13(15)10-6-2-1-3-7-10/h1-9,14H

117-99-7 Well-known Company Product Price

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  • Alfa Aesar

  • (L11100)  2-Hydroxybenzophenone, 99%   

  • 117-99-7

  • 5g

  • 641.0CNY

  • Detail
  • Alfa Aesar

  • (L11100)  2-Hydroxybenzophenone, 99%   

  • 117-99-7

  • 25g

  • 1601.0CNY

  • Detail

117-99-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Hydroxybenzophenone

1.2 Other means of identification

Product number -
Other names (2-Hydroxyphenyl)(phenyl)methanone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:117-99-7 SDS

117-99-7Related 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

117-99-7Relevant academic research and scientific papers

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

Basu, Mrinmoyee,Sarkar, Suresh,Pande, Surojit,Jana, Subhra,Kumar Sinha, Arun,Sarkar, Sougata,Pradhan, Mukul,Pal, Anjali,Pal, Tarasankar

, p. 7191 - 7193 (2009)

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

Selective Preparation of Xanthones from 2-Bromofluorobenzenes and Salicylaldehydes via Palladium-Catalyzed Acylation-SNAr Approach

Shen, Chaoren,Wu, Xiao-Feng

, p. 1269 - 1273 (2016)

A regioselective pathway for the preparation of xanthones from 2-bromofluorobenzenes and salicylaldehydes has been developed. The reaction proceeded through palladium-catalyzed acylation-SNAr sequence. Good to moderate yields of the desired xanthones were prepared in one step. Based on the results of control experiments, a possible reaction mechanism has been proposed.

Palladium-catalyzed coupling reaction of salicylaldehydes with aryl iodides via cleavage of the aldehyde C-H bond

Satoh, Tetsuya,Itaya, Tomoaki,Miura, Masahiro,Nomura, Masakatsu

, p. 823 - 824 (1996)

It has been found that the cross-coupling reaction of salicylaldehydes with aryl iodides smoothly proceeds by using a catalyst system of PdCl2/LiCl in the presence of Na2CO3 as base to give the corresponding 2-aroylphenols in good yields, which appears to involve cleavage of the aldehyde C-H bond.

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

Nowrouzi,Zarei,Roozbin

, p. 102448 - 102453 (2015)

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

Wang, Dahai,Cui, Sunliang

, p. 8511 - 8516 (2015)

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

Nowrouzi, Najmeh,Tarokh, Dariush

, p. 1493 - 1497 (2016)

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.

Intramolecular photocyclization of 2-acylphenyl methacrylates: A convenient access to 4,5-dihydro-1,4-epoxy-2-benzoxepin-3(1H)-ones =benzo[c]-6,8- dioxabicyclo [3.2.1]octan-7-ones

Nishio, Takehiko,Sakurai, Nobuharu,Iba, Kaoru,Hamano, Yo-Ichi,Sakamoto, Masami

, p. 2603 - 2609 (2005)

The photochemical reactions of 2-acylphenyl methacrylates (=2-acylphenyl 2-methylprop-2-enoates) 1 were investigated. Irradiation of 2-acylphenyl methacrylates 1a-d in MeCN gave the tricyclic lactones 2a-d in good yields, together with a small amount of O-C=O bond cleavage product, the 2-acylphenols 3a-d (Scheme 2, Table). The formation of the tricyclic lactones 2 probably follows a mechanism involving a 1,7-diradical through ζ-H abstraction (1,8-H transfer) by the excited carbonyl O-atom (Scheme 3). Irradiation of 2-acylphenyl tiglate (=2-acylphenyl (2E)-2-methylbut-2-enoate) 1e and 2-acylphenyl methacrylates 1g-i, substituted by a MeO group (δ-H) at the 3,5-positions of the phenylgroup, also gave the tricyclic lactones 2e and 2g-i, but in low yields. On the other hand, no H-abstraction products were observed on irridation of 2-(ethoxycarbonyl)phenyl methacrylate 1f, of 2-acylphenyl methacrylate 1j which is substituted by a Me group (γ-H) at the 3,5-positions of the phenyl group, and of 1k with an OH group at the 3-position of the phenyl group.

AN INTRAMOLECULAR OXENOID OXIDATION

Kumar, Shailendra,Murray, Robert W.

, p. 4781 - 4782 (1980)

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

Palladium-catalyzed direct C-H arylation of 2-hydroxybenzaldehydes with organic halides in neat water

Nowrouzi, Najmeh,Motevalli, Somayeh,Tarokh, Dariush

, p. 224 - 230 (2015)

The palladium-catalyzed cross-coupling of 2-hydroxybenzaldehydes with organic halides proceeds in the presence of n-Bu4NBr in H2O producing the corresponding 2-hydroxybenzophenones in high yields.

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

Xiao, Lin,Lang, Tao-Tao,Jiang, Ying,Zang, Zhong-Lin,Zhou, Cheng-He,Cai, Gui-Xin

, p. 3278 - 3283 (2021/02/01)

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.

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