143788-52-7

Basic information

• Product Name: (2S)-2-methyl-1,3-benzodithiole 1-oxide
• CAS NO: 143788-52-7
• Molecular Formula: C₈H₈OS₂
• Molecular Weight: 184.2785
• Mol File: 143788-52-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 352.5°C at 760 mmHg
• Flash Point: 167°C
• Density: 1.42g/cm³
• Vapor Pressure: 7.77E-05mmHg at 25°C
• Refractive Index: 1.718
• CAS DataBase Reference: (2S)-2-methyl-1,3-benzodithiole 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-methyl-1,3-benzodithiole 1-oxide(143788-52-7)
• EPA Substance Registry System: (2S)-2-methyl-1,3-benzodithiole 1-oxide(143788-52-7)

Safety Data

• Hazardous Substances Data: 143788-52-7(Hazardous Substances Data)

Upstream product

• 142181-68-8 cis-2-methyl-1,3-benzodithiole 1-oxide 
• 68486-94-2 2-methylbenzo[d][1,3]dithiole 
• 17534-15-5 Benzene-1,2-dithiol 

Relevant articles and documents

Dioxygenase-catalysed sulfoxidation of bicyclic alkylaryl sulfides and chemoenzymatic synthesis of acyclic disulfoxides

Toluene- and naphthalene-dioxygenase-catalysed oxidation of six bicyclic disulfide substrates, using whole cells of Pseudomonas putida, gave the corresponding monosulfoxides with high ee values and enantiocomplementarity, in most cases. Two alcohol-sulfox

Sulfoxides of High Enantiopurity from Bacterial Dioxygenase-catalysed Oxidation

Selected strains of the bacterium Pseudomonas putida (previously shown to effect dioxygenase-catalysed asymmetric cis-dihydroxylation of alkenes) have been found to yield chiral sulfoxides from the corresponding sulfides with a strong preference for the (R)- or (S)-configurations but without evidence of sulfone formation; similar results obtained using an Escherichia coli clone (pKST11, containing the Tod C1 C2 B and A genes encoding toluene dioxygenase from P. putida NCIMB 11767) are again consistent with a stereoselective dioxygenase-catalysed sulfoxidation.

Synthesis, Separation and Absolute Configuration Assignment to Enantiomers of 1,3-Benzodithiole 1-Oxide and 2-Alkyl-1,3-Benzodithiole 1-Oxides

1,3-Benzodithiole 1-oxide, 5, has been resolved into enantiomers using chiral stationary phase high performance liquid chromatography.Alkylation of an excess (25percent) of the late eluting (+)-(1R) enantiomer of the sulfoxide 5 under basic conditions yielded both cis and trans isomers of 2-methyl (6cis-1R,2S,6trans-1R,2R), 2-ethyl (7cis-1R,2S, 7trans-1R,2R) and 2-isopropyl (8cis-1R,2S, 8trans-1R,2R)-benzodithiole 1-oxide (25percent e.e.) and allowed a stereochemically correlation of absolute configuration between the suloxides 5 - 8. Treatment of racemic 1,3-benzodithiole 1-oxide (51S/51R) with potassium bis(trimethylsilyl)amide and (S)-(+)-1-iodo-2-methylbutane yielded four diastereoisomers of 2-(2'-methylbutyl)-1,3-benzodithiole 1-oxide (9cis-1R,2S,2'S, 9cis-1S,2R,2'S, 9trans-1S,2S,2'S, 9trans-1R,2R,2'S) which were separated by chiral stationary phase HPLC (CSP-HPLC).The most strongly retained diastereoisomer was analysed by X-ray crystallography and was assigned the (1S:1S:2'S) absolute configuration.Further alkylation of 9trans-1S,2S,2'S under similar conditions yielded 2-(2'S-methylbutyl)-2-(2"S-methylbutyl)-1,3-benzodithiole 1-oxide 10 of (1S,2'S,2"S) configuration exclusively.The same stereoisomer of the sulfoxide 10 was also obtained by dialkylation of the early eluting (-)-enantiomer of 1,3-benzodithiole 1-oxide (51S) using (+)-1-iodo-2-metrhylbutane, thus enabling the unequivocal establishment of the absolute configurations of the enantiomers of 1,3-benzodithiole 1-oxides listed in Table 1.A comparison of circular dichroism (CD) spectra for sulfoxides 5 - 9 indicates that this method may also be used to correlate absolute configurations of 2-alkyl substituted 1,3-benzodithiole 1-oxides.