479-21-0

Basic information

• Product Name: cotoin
• Synonyms: cotoin;2,6-Dihydroxy-4-methoxybenzophenone
• CAS NO: 479-21-0
• Molecular Formula: C₁₄H₁₂O₄
• Molecular Weight: 244.2427
• Mol File: 479-21-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 131-132°
• Boiling Point: 347.16°C (rough estimate)
• Flash Point: 153.3°C
• Appearance: /
• Density: 1.2379 (rough estimate)
• Vapor Pressure: 4.81E-07mmHg at 25°C
• Refractive Index: 1.5389 (estimate)
• PKA: 7.00±0.40(Predicted)
• CAS DataBase Reference: cotoin(CAS DataBase Reference)
• NIST Chemistry Reference: cotoin(479-21-0)
• EPA Substance Registry System: cotoin(479-21-0)

Safety Data

• Hazardous Substances Data: 479-21-0(Hazardous Substances Data)

Usage

Preparation

Obtained by reaction of benzonitrile with phloroglucinol monomethyl ether (Hoesch reaction).

InChI:InChI=1/C14H12O4/c1-18-10-7-11(15)13(12(16)8-10)14(17)9-5-3-2-4-6-9/h2-8,15-16H,1H3

Upstream product

• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 
• 3555-86-0 2-benzoylphloroglucinol 
• 2174-64-3 5-methoxyresorcinol 
• 98-88-4 benzoyl chloride 
• 108-73-6 3,5-dihydroxyphenol 
• 621-23-8 1,2,3-trimethoxybenzene 
• 3770-80-7 2,4,6-trimethoxybenzophenone 
• 125557-63-3 4-Methoxy-3-methyl-6-(2-oxo-2-phenyl-ethyl)-pyran-2-one 

Downstream Products

• 34425-64-4 2-hydroxy-4,6-dimethoxybenzophenone 
• 860594-33-8 2-ethoxy-6-hydroxy-4-methoxy-benzophenone 
• 1159706-94-1 (3,5-diallyl-2,6-dihydroxy-4-methoxyphenyl)(phenyl)methanone 
• 87338-97-4 (2,6-dihydroxy-4-methoxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl)(phenyl)methanone 
• 1570098-55-3 (3,5-diallyl-2,4,6-trihydroxyphenyl)(phenyl)methanone 

Relevant articles and documents

Three new benzophenone-xanthone dimers from the root of Garcinia dulcis

Investigation of the chemical constituents of the roots of Garcinia dulcis resulted in the isolation of three new benzophenone-xanthone dimers named garciduols A-C (1-3) in addition to a new xanthone, 1,3,6-trihydroxy- 7-methoxyxanthone (4). Five known xanthones [2,5-dihydroxy-1-methoxy-(5), 1,4,5-trihydroxy-(6), 1,3,5-trihydroxy-(7), 1,3,6-trihydroxy-5-methoxy- (8) and 1,3,6-trihydroxy-8-isoprenyl-7-methoxyxanthone (9)] were also isolated from the roots. Their structures were determined by spectroscopic analysis including two dimensional NMR. The behaviors of chemical shifts caused by acetylation and the position of the methoxyl group in the dimers characterized by model synthetic benzophenones are also discussed.

Asymmetric Dearomatization/Cyclization Enables Access to Polycyclic Chemotypes

Enantioenriched, polycyclic compounds were obtained from a simple acylphloroglucinol scaffold. Highly enantioselective dearomatization was accomplished using a Trost ligand–palladium(0) complex. A computational DFT model was developed to rationalize observed enantioselectivities and revealed a key reactant-ligand hydrogen bonding interaction. Dearomatized products were used in visible light-mediated photocycloadditions and oxidative free radical cyclizations to obtain novel polycyclic chemotypes including tricyclo[4.3.1.01,4]decan-10-ones, bicyclo[3.2.1]octan-8-ones and highly substituted cycloheptanones.

Asymmetric, stereodivergent synthesis of (-)-clusianone utilizing a biomimetic cationic cyclization

We report a stereodivergent, asymmetric total synthesis of (-)-clusianone in six steps from commercial materials. We implement a challenging cationic cyclization forging a bond between two sterically encumbered quaternary carbon atoms. Mechanistic studies point to the unique ability of formic acid to mediate the cyclization forming the clusianone framework. Aim for selectivity: (-)-Clusianone was produced by a stereodivergent asymmetric total synthesis in six steps from commercial materials. The synthesis utilizes a challenging formic acid-mediated cationic cyclization forging a bond between two sterically encumbered quaternary carbon atoms.