67512-92-9

Basic information

• Product Name: 4-methyltetrahydro-2H-thiopyran 1,1-dioxide
• Synonyms: 2H-thiopyran, tetrahydro-4-methyl-, 1,1-dioxide; 4-Methyltetrahydro-2H-thiopyran 1,1-dioxide; 4-Methylthiane, S,S-dioxide
• CAS NO: 67512-92-9
• Molecular Formula: C₆H₁₂O₂S
• Molecular Weight: 148.2233
• Mol File: 67512-92-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 196°C at 760 mmHg
• Flash Point: 50.9°C
• Density: 1.114g/cm³
• Vapor Pressure: 0.573mmHg at 25°C
• Refractive Index: 1.462
• CAS DataBase Reference: 4-methyltetrahydro-2H-thiopyran 1,1-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methyltetrahydro-2H-thiopyran 1,1-dioxide(67512-92-9)
• EPA Substance Registry System: 4-methyltetrahydro-2H-thiopyran 1,1-dioxide(67512-92-9)

Safety Data

• Hazardous Substances Data: 67512-92-9(Hazardous Substances Data)

Upstream product

• 6829-42-1 diethyl 3-methylglutarate 
• 4457-72-1 3-methyl-1,5-dibromopentane 
• 500862-51-1 3-methyl-1,5-pentanediyl dimesylate 
• 473330-05-1 S-(3-methylbut-3-en-1-yl) ethanethioate 
• 473330-09-5 1-phenylselenyl-2-thia-5-methyl-5-hexene 
• 80352-66-5 4-mesyloxy-2-methylbutene 
• 4457-71-0 3-methylpentane-1,5-diol 
• 473330-14-2 (3-methyl-but-3-ene-1-sulfonylmethylselanyl)-benzene 
• 5161-17-1 tetrahydro-4-methyl-2H-thiopyran 

Relevant articles and documents

Stereoelectronic Effects: Perlin Effects in Thiane-Derived Compounds

Stereoelectronic effects in thianes and thiane-derived sulfoxides, sulfones, sulfilimines, and sulfoximines were investigated by measuring 1JC,H coupling constants and by identification of normal and reversed Perlin effects, i.e., of differences in the coupling constants for equatorial and axial C–H bonds in the methylene groups of six-membered rings. The Perlin effects were correlated with results from natural bond orbital (NBO) analyses. NMR experiments were performed with conformationally restricted dimethyl- or tert-butyl-substituted derivatives, while the parent compounds were used for calculations. It turned out that the coupling constants are not only strongly influenced by stereoelectronic interactions with antiperiplanar C–H, C–C, C–O, and C–N bonds, but by the s character of the respective C–H bonds' carbon orbital as well.

Regioselectivity of ring closure of 2-thia- and 2-sulfonyl-5-methyl-5-hexenyl radicals

(matrix presented) Ring closure of the α-substituted radicals 4 (X = S, SO2) is observed to be irreversible and to lead to significant amounts of the product of 6-endo cyclization. Indeed, reduction of the sulfonyl-based radical 4 (X = SO2