26524-91-4

Basic information

• Product Name: 4-Oxo-2,3-dihydro-4H-1-benzothiopyran 1-oxide
• Synonyms: 4-Oxothiochroman 1-oxide;Thiochromanone 1-oxide;thiochroman-4-one 1-oxide;2,3-Dihydro-4H-1-benzothiopyran-4-one 1-oxide;2,3-Dihydro-4-oxo-4H-1-benzothiopyran 1-oxide;3,4-Dihydro-4-oxo-2H-1-benzothiopyran 1-oxide;4-Oxo-2,3-dihydro-4H-1-benzothiopyran 1-oxide
• CAS NO: 26524-91-4
• Molecular Formula: C₉H₈O₂S
• Molecular Weight: 180.22
• Mol File: 26524-91-4.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Oxo-2,3-dihydro-4H-1-benzothiopyran 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Oxo-2,3-dihydro-4H-1-benzothiopyran 1-oxide(26524-91-4)
• EPA Substance Registry System: 4-Oxo-2,3-dihydro-4H-1-benzothiopyran 1-oxide(26524-91-4)

Safety Data

• Hazardous Substances Data: 26524-91-4(Hazardous Substances Data)

Upstream product

• 3528-17-4 2,3-dihydro-4H-[1]benzothiopyran-4-one 
• 127-65-1 chloroamine-T 

Downstream Products

• 74695-69-5 5,10-Dioxo-5,10-dihydro-10λ⁴-thia-4a-aza-benzo[b]fluorene-11-carboxylic acid phenylamide 
• 3844-31-3 trans-thioindigo 

Relevant articles and documents

Chemo- and diastereoselectivity in the dimethyldioxirane oxidation of 2,3-dihydro-4H-1-benzothiopyran-4-ones and 4H-1-benzothiopyran-4-ones. Unusual reactivity of 4H-1-benzothiopyran-4-one 1-oxides1

The oxidation of the 1-thiochromanones 1-3 by dimethyldioxirane (DMD) produced the corresponding sulfoxides 4-6 or sulfones 7-9; their relative amounts depended on the amount of oxidant used. A low diastereoselectivity was observed in the sulfoxidation of

Chloroperoxidase-catalyzed asymmetric synthesis of a series of aromatic cyclic sulfoxides

The chloroperoxidase (CPO) catalyzed oxidation of a series of rigid aromatic sulfides of well-defined geometry has been studied by the use of enantioselective gas chromatography for the determination of product composition and sulfoxide enantiomeric excess. The almost planar 1-thiaindane was found to be an excellent substrate, giving a quantitative yield of the (-)-(R)-1-oxide in 99% e.e. The sterically more demanding next higher homolog with a six-membered heterocyclic ring, 1-thiatetrahydronaphthalene (1-thiochroman), also gave a sulfoxide in high e.e. (≥ 96%) but in a much lower yield, indicating a preserved stereorecognition ability but a lower turnover rate. A carbonyl group in the 4-position (1-thiochroman-4-one) had no further effect on the CPO-mediated sulfoxidation. Enantio-selectivity was lost for the symmetric disulfide, 1,3-benzodithiol, indicating an equal accessibility of the Fe=O complex towards both sulfur atoms and an active site centred above the heme-iron atom. In all cases with pronounced enantioselectivity the reaction gave the (R)-sulfoxide as observed previously with alkyl aryl sulfides. A change of oxygen source from hydrogen peroxide to t-butyl hydroperoxide and a longer reaction time gave a higher chemical but a lower optical yield, most likely due to an increased competition by the uncatalyzed oxidation reaction in this case.

SULFILIMINES IN ORGANIC SYNTHESES: NEW ENTRIES INTO TETRAHYDRO-1,2-BENZOTHIAZEPINE AND 1,2-BENZISOTHIAZOLE SYSTEMS

Novel ring transformations of thiochroman-4-ones and benzothiophen-3(2H)-ones to tetrahydro-1,2-benzothiazepin-5-ones and 1,2-benzisothiazoles via sulfilimine intermediates are described.