13020-57-0

Basic information

• Product Name: 3-HYDROXYBENZOPHENONE
• Synonyms: (3-Hydroxyphenyl)(phenyl)methanone;Methanone, (3-hydroxyphenyl)phenyl-;M-HYDROXYBENZOPHENONE;3-HYDROXYBENZOPHENONE;M-BENZOYL PHENOL;3-Hydroxybenzophenone,99%
• CAS NO: 13020-57-0
• Molecular Formula: C₁₃H₁₀O₂
• Molecular Weight: 198.22
• EINECS: 235-879-1
• Product Categories: Aromatic Benzophenones & Derivatives (substituted);Linkers for Solid Phase Synthesis;Benzophenone;Organic Photoinitiators;Polymerization Initiators
• Mol File: 13020-57-0.mol

Chemical Properties

• Melting Point: 113-115 °C(lit.)
• Boiling Point: 295.53°C (rough estimate)
• Flash Point: 159.5 °C
• Appearance: light beige to brown-grey crystalline powder
• Density: 1.1184 (rough estimate)
• Vapor Pressure: 4.1E-06mmHg at 25°C
• Refractive Index: 1.5954 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Soluble in Chloroform, DCM. Ethyl Acetate.
• PKA: 9.18±0.10(Predicted)
• CAS DataBase Reference: 3-HYDROXYBENZOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXYBENZOPHENONE(13020-57-0)
• EPA Substance Registry System: 3-HYDROXYBENZOPHENONE(13020-57-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• RTECS: PC4959730
• HazardClass: IRRITANT
• Hazardous Substances Data: 13020-57-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
3-Hydroxybenzophenone serves as a more attractive hydrogen bonding co-material for MCPBA, due to the inability of the 3-hydroxyl group to form an intramolecular hydrogen bond. This property enhances its utility in chemical synthesis processes.
Used in Photochemistry:
3-Hydroxybenzophenone is commonly utilized as a radical and cationic photo initiator. Its photochemical properties make it a valuable component in various photo-initiated reactions and processes.

Preparation

Preparation by aromatization of 5-benzoyl-2- cyclohexenone, ? in the presence of 10% Pd/C in refluxing xylene for 6 h (60%) ? in the presence of lithium bromide and cupric bromide in refluxing acetonitrile for 1 h (75%).

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

Upstream product

• 119-61-9 benzophenone 
• 134172-65-9 m-methoxybenzhydrol 
• 6136-67-0 3-methoxybenzophenone 
• 2835-78-1 3-amino benzophenone 
• 1711-05-3 m-anisoyl chloride 
• 71-43-2 benzene 
• 591-20-8 3-Bromophenol 
• 6919-61-5 N-methoxy-N-methylbenzamide 
• 118043-80-4 m-benzoyltriphenylmethyl peroxide 
• 154386-86-4 5-benzoyl-2-cyclohexenone 
• 100-52-7 benzaldehyde 
• 586-38-9 3-Methoxybenzoic acid 
• 99-06-9 3-Carboxyphenol 
• 98-80-6 phenylboronic acid 

Downstream Products

• 93021-98-8 Allyl-<3-benzoyl-phenyl>-aether 
• 117819-33-7 (R)-(+) ethyl 2-(3-benzoylphenoxy)propionate 
• 76981-68-5 (3-Benzoyl-phenoxy)-acetic acid ethyl ester 
• 74167-91-2 ethyl2-(3-benzoylphenoxy)propanoate 
• 83355-40-2 Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-(3-benzoyl-phenoxy)-tetrahydro-pyran-3-yl ester 
• 91692-34-1 2,4,6-Triiod-3-hydroxy-benzophenon 
• 38111-73-8 3-(1-Hydroxy-2-methanesulfinyl-1-phenyl-ethyl)-phenol 
• 196311-88-3 {3-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-but-2-enyloxy]-phenyl}-phenyl-methanone 
• 196312-01-3 {3-[(2E,6E)-8-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-octa-2,6-dienyloxy]-phenyl}-phenyl-methanone 
• 30074-03-4 3'-Hydroxyphenytoin 
• 1028288-37-0 {3-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy]-phenyl}-phenyl-methanone 

Relevant articles and documents

Iron-catalyzed arene C-H hydroxylation

The sustainable, undirected, and selective catalytic hydroxylation of arenes remains an ongoing research challenge because of the relative inertness of aryl carbon-hydrogen bonds, the higher reactivity of the phenolic products leading to over-oxidized by-products, and the frequently insufficient regioselectivity. We report that iron coordinated by a bioinspired L-cystine-derived ligand can catalyze undirected arene carbon-hydrogen hydroxylation with hydrogen peroxide as the terminal oxidant. The reaction is distinguished by its broad substrate scope, excellent selectivity, and good yields, and it showcases compatibility with oxidation-sensitive functional groups, such as alcohols, polyphenols, aldehydes, and even a boronic acid. This method is well suited for the synthesis of polyphenols through multiple carbon-hydrogen hydroxylations, as well as the late-stage functionalization of natural products and drug molecules.

Selective Oxidation of Alkylarenes to the Aromatic Ketones or Benzaldehydes with Water

Here a palladium-catalyzed oxidation method for converting alkylarenes into the aromatic ketones or benzaldehydes with water as the only oxygen donor is reported. This C-H bond oxidation functionalization does not require other oxidants and hydrogen accep

Enantioselective synthesis of 3-substituted dihydrobenzofurans through iridium-catalyzed intramolecular hydroarylation

Intramolecular hydroarylationviaC-H activation is one of the most powerful methods to synthesize carbo- and heterocyclic compounds, whereas we still have room for developing a highly enantioselective variant of the reaction. Here we describe Ir-catalyzed enantioselective intramolecular hydroarylation ofm-allyloxyphenyl ketones. The enantioselective cyclization was efficiently catalyzed by a cationic iridium complex coordinated with a conventional chiral bisphosphine ligand to give benzofurans in high yields with high enantioselectivity. A carbonyl group of ketones functioned as an effective directing group for the C-H activation. In terms of synthetic utility, we also achieved one-pot synthesis of chiral 3-substituted dihydrobenzofurans from readily available allylic carbonates andm-hydroxyacetophenonesviasequential Pd-catalyzed allylic substitution and Ir-catalyzed intramolecular hydroarylation.

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.

Arylation of Aldehydes to Directly Form Ketones via Tandem Nickel Catalysis

A nickel-catalyzed arylation of both aliphatic and aromatic aldehydes proceeds with air-stable (hetero)arylboronic acids, with an exceptionally wide substrate scope. The neutral condition tolerates acidic hydrogen and sensitive polar groups and also preserves α-stereocenters of some chiral aldehydes. Interestingly, this nickel(0) catalysis does not follow common 1,2-insertion of arylmetal species to aldehydes and β-hydrogen elimination.

A Nickel-Catalyzed Carbonyl-Heck Reaction

The use of transition-metal catalysis to enable the coupling of readily available organic molecules has greatly enhanced the ability of chemists to access complex chemical structures. In this work, an intermolecular coupling reaction that unites organotriflates and aldehydes is presented. A unique catalyst system is identified to enable this reaction, featuring a Ni0 precatalyst, a tridentate Triphos ligand, and a bulky amine base. This transformation provides access to a variety of ketone-containing products without the selectivity- and reactivity-related challenges associated with more traditional Friedel–Crafts reactions. A Heck-type mechanism is postulated, wherein the π bond of the aldehyde takes the role of the olefin in the insertion/elimination steps.

Photocatalytic Hydrogen-Evolution Cross-Couplings: Benzene C-H Amination and Hydroxylation

We present a blueprint for aromatic C-H functionalization via a combination of photocatalysis and cobalt catalysis and describe the utility of this strategy for benzene amination and hydroxylation. Without any sacrificial oxidant, we could use the dual catalyst system to produce aniline directly from benzene and ammonia, and phenol from benzene and water, both with evolution of hydrogen gas under unusually mild conditions in excellent yields and selectivities.

Design and synthesis of cyclic acylguanidines as BACE1 inhibitors

Based on the lead compound 1 reported in literature, a series of novel BACE1 inhibitors were designed and synthesized, among which compound 11 exhibited a 14-fold improvement in potency over the lead compound 1. This represents a good lead for the discovery of more promising BACE1 inhibitors for the potential treatment of AD.

BENZHYDRYL DERIVATIVES FOR THE TREATMENT OF RESPIRATORY DISEASES

The invention relates to novel compounds of formula (I) having a benzhydryl structure which are both phosphodiesterase 4 (PDE4) enzyme inhibitors and muscarinic M3 receptor antagonists, methods of preparing such compounds, compositions containing them and therapeutic use thereof.

BENZHYDRYL DERIVATIVES

Compounds having a benzhydryl structure represented by formula (I) described herein are both phosphodiesterase 4 (PDE4) enzyme inhibitors and muscarinic M3 receptor antagonists and are useful for treating diseases of the respiratory tract.