835-11-0

Basic information

• Product Name: 2,2'-DIHYDROXYBENZOPHENONE
• Synonyms: AURORA KA-485;2,2'-Dihydroxybenzophenone 98%;Benzophenone, 2,2'-dihydroxy-;Bis-(2-hydroxy-phenyl)-methanone;Bis(2-hydroxyphenyl)methanone;Methanone, bis(2-hydroxyphenyl)-;Methanone,bis(2-hydroxyphenyl)-;2,2'-DIHYDROXYBENZOPHENONE
• CAS NO: 835-11-0
• Molecular Formula: C₁₃H₁₀O₃
• Molecular Weight: 214.22
• EINECS: 212-639-4
• Product Categories: Benzophenones (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;C13 to C14;Carbonyl Compounds;Ketones;Building Blocks;C13 to C14;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 835-11-0.mol
• Article Data: 14

Chemical Properties

• Melting Point: 61-62.5 °C(lit.)
• Boiling Point: 333°C (estimate)
• Flash Point: 166.8 °C
• Appearance: /
• Density: 1.1956 (rough estimate)
• Refractive Index: 1.5090 (estimate)
• Solubility: almost transparency in Methanol
• PKA: 7.32±0.30(Predicted)
• CAS DataBase Reference: 2,2'-DIHYDROXYBENZOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-DIHYDROXYBENZOPHENONE(835-11-0)
• EPA Substance Registry System: 2,2'-DIHYDROXYBENZOPHENONE(835-11-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 835-11-0(Hazardous Substances Data)

Usage

Preparation

Preparation by diazotization of 4,4′-diamino-2,2′- di-hydroxybenzophenone in diluted hydrochloric acid, followed by treatment with 50% phosphorous acid at 0° for 1 h, then at r.t. for 24 h (34%).

Upstream product

• 7446-70-0 aluminium trichloride 
• 134-55-4 phenyl 2-acetoxybenzoate 
• 98-95-3 nitrobenzene 
• 201230-82-2 carbon monoxide 
• 89466-08-0 2-hydroxyphenyl boronic acid 
• 13102-33-5 2,2'-dimethoxybenzophenone 
• 578-57-4 2-bromoanisole 
• 77464-21-2 2-methoxy-α-(2-methoxyphenyl)benzenemethanol 
• 135-02-4 ortho-anisaldehyde 
• 2467-02-9 Bis(2-hydroxyphenyl)methane 
• 533-58-4 2-Iodophenol 
• 90-02-8 salicylaldehyde 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 119-61-9 benzophenone 

Downstream Products

• 39265-09-3 N-(3-Dimethylaminopropyl)-2,2'-dihydroxy-diphenylketoimin 
• 91955-15-6 2,2'-Dihydroxy-benzophenon-hydrazon 
• 95950-25-7 2,2',2'',2'''-Tetrahydroxy-benzophenon-azin 
• 97990-55-1 2,2'-Dihydroxybenzophenon-dimethylhydrazon 
• 90-47-1 xanth-9-one 
• 7732-18-5 water 
• 124-38-9 carbon dioxide 
• 69-72-7 salicylic acid 
• 108-95-2 phenol 
• 92-83-1 xanthene 
• 109689-81-8 2,2'-dihydroxy-benzophenone-(2,4-dinitro-phenylhydrazone) 
• 845821-92-3 2,2’-bis(diphenylphosphino)-benzophenone 
• 845821-98-9 bis{2-[bis(3,5-dimethylphenyl)phosphanyl]phenyl}methanone 

Relevant articles and documents

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

Rhodium-Catalyzed Directing-Group-Assisted Aldehydic C–H Arylations with Aryl Halides

A rhodium-catalyzed general protocol for the directing-group-assisted arylation of aromatic aldehydic C–H bonds was developed. This method involves either hydroxy- or amino-group-directed aldehyde C–H arylation with various aryl halides. A broad synthetic scope for the preparation of 2-hydroxybenzophenones was established with electronically variant salicylaldehydes and aryl halides with chemo- and regioselective possibilities. The developed protocol was also applied in the synthesis of medicinally important 3-salicyloylpyridines in high yields.

2,2′-Dihydroxybenzophenones and their carbonyl N-analogues as inhibitor scaffolds for MDR-involved human glutathione transferase isoenzyme A1-1

The MDR-involved human GSTA1-1, an important isoenzyme overexpressed in several tumors leading to chemotherapeutic-resistant tumour cells, has been targeted by 2,2′-dihydroxybenzophenones and some of their carbonyl N-analogues, as its potential inhibitors. A structure-based library of the latter was built-up by a nucleophilic cleavage of suitably substituted xanthones to 2,2′-dihydroxy-benzophenones (5-9) and subsequent formation of their N-derivatives (oximes 11-13 and N-acyl hydrazones 14-16). Screening against hGSTA1-1 led to benzophenones 6 and 8, and hydrazones 14 and 16, having the highest inhibition potency (IC50 values in the range 0.18 ± 0.02 to 1.77 ± 0.10 μM). Enzyme inhibition kinetics, molecular modeling and docking studies showed that they interact primarily at the CDNB-binding catalytic site of the enzyme. In addition, the results from cytotoxicity studies with human colon adenocarcinoma cells showed low LC 50 values for benzophenone 6 and its N-acyl hydrazone analogue 14 (31.4 ± 0.4 μM and 87 ± 1.9 μM, respectively), in addition to the strong enzyme inhibition profile (IC50(6 ) = 1,77 ± 0.10 μM; IC50(14 ) = 0.33 ± 0.05 μM). These structures may serve as leads for the design of new potent mono- and bi-functional inhibitors and pro-drugs against human GTSs.