784-62-3

Basic information

• Product Name: 1-THIOFLAVONE
• Synonyms: 2-phenyl-4h-1-benzothiopyran-4-on;4H-1-Benzothiopyran-4-one,2-phenyl-;1-THIOFLAVONE;2-PHENYLTHIOCHROMEN-4-ONE;2-PHENYLTHIOCHROMEN-4-ONE 98%;THIOFLAVONE;2-Phenyl-4H-1-benzothiopyran-4-one
• CAS NO: 784-62-3
• Molecular Formula: C₁₅H₁₀OS
• Molecular Weight: 238.3
• Mol File: 784-62-3.mol
• Article Data: 40

Chemical Properties

• Melting Point: 125-127 °C(lit.)
• Boiling Point: 389.4°C at 760 mmHg
• Flash Point: 215.3°C
• Appearance: /
• Density: 1.269g/cm³
• Vapor Pressure: 2.86E-06mmHg at 25°C
• Refractive Index: 1.677
• CAS DataBase Reference: 1-THIOFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-THIOFLAVONE(784-62-3)
• EPA Substance Registry System: 1-THIOFLAVONE(784-62-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 784-62-3(Hazardous Substances Data)

Usage

Purification Methods

This yellow solid is purified by passage through a silica gel column, eluting with *C6H6/Me6CO, evaporating and crystallising the residue from EtOH. The sulfoxide [65373-82-2] has m 133-135o, and the sulfone [22810-82-2] has m 136.5-137o (from EtOH). The dimethylhydrazone has m 111-113o (from BuOH). It forms easily hydrolysable salts. [Nakazumi et al. J Heterocycl Chem 21 193 1984, Chen et al. J Org Chem 51 3282 1986, Van Allen & Reynolds J Heterocycl Chem 8 807 1971, Beilstein 17 I 204, 17 III/IV 5420, 17/10 V 560.]

InChI:InChI=1/C15H10OS/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-10H

Upstream product

• 34875-24-6 3-phenyl-3-(phenylthio)acrylic acid 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 108-98-5 thiophenol 
• 3739-97-7 (trimethylsilyl)methylenetriphenylphosphorane 
• 405271-41-2 C₂₀H₂₄O₃SSi 
• 929083-19-2 1-[2-(1,1-dimethylethylsulfanyl)phenyl]ethanone 
• 1402911-67-4 1-[2-(1,1-dimethylethylsulfanyl)phenyl]-3-phenylprop-2-en-1-one 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 1311381-55-1 (E)-1-(2-(methylthio)phenyl)-3-phenylprop-2-en-1-one 
• 1441-97-0 2'-(methylthio)acetophenone 
• 100-52-7 benzaldehyde 
• 2142-69-0 2-bromophenyl methyl ketone 
• 117968-45-3 3-Methanesulfinyl-2-phenyl-thiochroman-4-one 
• 34875-02-0 ethyl (Z)-3-phenyl-3-(phenylthio)acrylate 

Downstream Products

• 86296-62-0 2-benzoylbenzothiophen-3(2H)-one 1,1-dioxide 
• 1174711-77-3 1-thioflavone thiosemicarbazone 
• 1619229-33-2 (Z)-5-(1,2-diphenylvinyl)-2-phenyl-4H-thiochromen-4-one 
• 1619229-34-3 (Z)-5-(1,2-diphenylvinyl)-2-phenyl-4H-thiochromen-4-one 
• 6928-51-4 2-phenylthiochroman-4-ol 
• 105703-74-0 3-Octyloxymethyl-2-phenyl-thiochromen-4-one 
• 105703-73-9 3-Hexyloxymethyl-2-phenyl-thiochromen-4-one 
• 105703-72-8 3-Butoxymethyl-2-phenyl-thiochromen-4-one 
• 96883-65-7 3-Ethoxymethyl-2-phenyl-thiochromen-4-one 
• 96883-67-9 3-Chloromethyl-1,1-dioxo-2-phenyl-1H-1λ⁶-thiochromen-4-one 
• 96883-64-6 3-Methoxymethyl-2-phenyl-4H-1-benzothiopyran-4-one 
• 77694-72-5 3-bromo-2-phenylthiochromone 1,1-dioxide 
• 84477-06-5 tribenzo-phenyl-bis(thiopyranylidene)ethene 
• 103225-47-4 4-(dicyanomethylene)4H-thioflavene 1,1-dioxide 

Relevant articles and documents

Catalytic Enantioselective Synthesis of 3,4-Unsubstituted Thiochromenes through Sulfa-Michael/Julia-Kocienski Olefination Cascade Reaction

A highly enantioselective cascade sulfa-Michael/Julia-Kocienski olefination reaction between 2-mercaptobenzaldehydes and β-substituted vinyl PT-sulfones has been realized for the synthesis of 3,4-unsubstituted 2H-thiochromenes. This reaction, catalyzed by diphenylprolinol TMS ether, proceeds through an aromatic iminium intermediate and furnishes a wide range of 2-substiuted 2H-thiochromenes with excellent enantioselectivities (up to 99:1 er).

Elemental chalcogen (Se, S) in PEG-400 to the synthesis of seleno- And thioflavones from 2-chlorophenyl ethynyl ketone and nucleophilic species of chalcogen

An alternative green method was developed for the synthesis of thio- and selenoflavones by the ring closure of 2-chlorophenyl ethynyl ketone with NaHY (Y = S, Se). These nucleophilic chalcogen species were generated in situ using NaBH4 to reduc

Conjugate addition of grignard reagents to thiochromones catalyzed by copper salts: A unified approach to both 2-alkylthiochroman-4-one and thioflavanone

Grignard reagents undergo conjugate addition to thiochromones catalyzed by copper salts to afford 2-substituted-thiochroman-4-ones, both 2-alkylthiochroman-4-ones and thioflavanones (2-arylthiochroman-4-ones), in good yields with trimethylsilyl chloride (TMSCl) as an additive. The best yields of 1,4-adducts can be attained with CuCN-2LiCl as the copper source. Excellent yields of 2-alkyl-substituted thiochroman-4-ones and thioflavanones (2-aryl substituted) are attained with a broad range of Grignard reagents. This approach works well with both alkyl and aromatic Grignard reagents, thus providing a unified synthetic approach to privileged 2-substituted thiochroman-4-ones and a potential valuable precursor for further synthetic applications towards many pharmaceutically active molecules. The use of commercially available and/or readily prepared Grignard reagents will expedite the synthesis of a large library of both 2-alkyl substituted thiochroman-4-ones and thioflavanones for additional synthetic applications.