68486-94-2

Basic information

• Product Name: 2-methyl-1,3-benzodithiole
• Synonyms: 1,3-Benzodithiole, 2-methyl-
• CAS NO: 68486-94-2
• Molecular Formula: C₈H₈S₂
• Molecular Weight: 168.2791
• Mol File: 68486-94-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 251.7°C at 760 mmHg
• Flash Point: 109.5°C
• Density: 1.224g/cm³
• Vapor Pressure: 0.0321mmHg at 25°C
• Refractive Index: 1.651
• CAS DataBase Reference: 2-methyl-1,3-benzodithiole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyl-1,3-benzodithiole(68486-94-2)
• EPA Substance Registry System: 2-methyl-1,3-benzodithiole(68486-94-2)

Safety Data

• Hazardous Substances Data: 68486-94-2(Hazardous Substances Data)

Upstream product

• 75-15-0 carbon disulfide 
• 274-30-6 1,3-benzodithiol 
• 74-88-4 methyl iodide 
• 75-07-0 acetaldehyde 
• 17534-15-5 Benzene-1,2-dithiol 

Downstream Products

• 143788-51-6 (-)-(1S,2R)-2-methyl-1,3-benzodithiole-1-oxide 
• 143788-52-7 (-)-(1S,2S)-2-methyl-1,3-benzodithiole-1-oxide 
• 142235-68-5 (+)-trans-2-methyl-1,3-benzodithiole 1-oxide 
• 142181-68-8 (+)-cis-2-methyl-1,3-benzodithiole 1-oxide 
• 142181-68-8 cis-2-methyl-1,3-benzodithiole 1-oxide 
• 142181-68-8 trans-2-methyl-1,3-benzodithiole 1-oxide 

Relevant articles and documents

REACTIONS OF 2-LITHIO-1,3-BENZODITHIOLE WITH CARBON DISULFIDE: FORTH AND BACK PROCESSES

Carbophilic reaction of 2-lithio-1,3-benzodithiole with CS2, followed by the addition of a second base equivalent and quenching with MeI, yields 2--1,3-benzodithiole.An unexpected pathway mediated by MeS- and leading to the reformation of the 1,3-benzodithiole anion is described.

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.