methanesulfinyl(methylsulfanyl)methane

• ChemBase ID: 137873
• Molecular Formular: C3H8OS2
• Molecular Mass: 124.22502
• Monoisotopic Mass: 124.00165688
• SMILES: CSCS(=O)C
• Canonical SMILES: CSCS(=O)C
• InChI: InChI=1S/C3H8OS2/c1-5-3-6(2)4/h3H2,1-2H3
• InChIKey: OTKFCIVOVKCFHR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methanesulfinyl(methylsulfanyl)methane
• IUPAC Traditional name: methanesulfinyl(methylsulfanyl)methane
• Synonyms: MMTS; Formaldehyde dimethyl mercaptal S-oxide; Methyl methylmercaptomethyl sulfoxide; Methyl methylsulfinylmethyl sulfide; Methyl methylthiomethyl sulfoxide; Formaldehyde dimethyl thioacetal monoxide; Methyl (methylsulfinyl)methyl sulfide; Methyl (methylthio)methyl sulfoxide; (甲基硫代)甲基亚砜甲酯; 甲基甲硫甲基亚砜; 甲醛二甲基缩硫醛硫氧化物; 甲基甲基硫代甲砜; (甲基硫代)甲基亚砜甲酯

Database IDs

• CAS Number: 33577-16-1
• EC Number: 251-577-2
• MDL Number: MFCD00002091
• Beilstein Number: 906789
• PubChem SID: 162232134
• PubChem CID: 99129

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -0.55826473
• LogD (pH = 7.4): -0.55826473
• Log P: -0.55826473
• Molar Refractivity: 32.7642 cm^3
• Polarizability: 12.941599 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 222-226°C
• Flash Point: >110°C(230°F); 113 °C; 235.4 °F
• Density: 1.222
• Refractive Index: 1.5520

Safety Information

• Storage Warning: Hygroscopic
• German water hazard class: 3
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Product Information

• Purity: 97%
• Linear Formula: CH3SOCH2SCH3

REFERENCES

• Readily undergoes metallation with NaH, n-BuLi, etc. to give a useful formaldehyde anion synthon. Products are readily hydrolyzed by acid.
• Monoalkylation with alkyl halides: Tetrahedron Lett., 3151 (1971), or terminal epoxides leads to the homologated aldehydes: J. Org. Chem., 39, 3645 (1974). Dialkylation with alkyl halides affords, after hydrolysis, symmetrical ketones: Synthesis, 117 (1974). This reaction has also been applied to the synthesis of cyclobutanones and other cycloalkanones: Tetrahedron Lett., 3653 (1974); 2767 (1975). A Knoevenagel reaction with aryl aldehydes gives the ketene thioacetal monosulfoxide, readily solvolyzed in alcoholic HCl to an arylacetic ester: Tetrahedron Lett., 1383 (1972):
  
• With ketones, the lithio-derivative gives, after hydrolysis, ɑ-hydroxy aldehydes, not readily available by other routes: Tetrahedron Lett., 2681 (1972). Elimination from the intermediate adduct has also been used as a route to substituted acetic acids: Synthesis, 880 (1979).