methanesulfinylbenzene

• ChemBase ID: 87284
• Molecular Formular: C7H8OS
• Molecular Mass: 140.20282
• Monoisotopic Mass: 140.02958588
• SMILES: S(=O)(c1ccccc1)C
• Canonical SMILES: CS(=O)c1ccccc1
• InChI: InChI=1S/C7H8OS/c1-9(8)7-5-3-2-4-6-7/h2-6H,1H3
• InChIKey: JXTGICXCHWMCPM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methanesulfinylbenzene
• IUPAC Traditional name: methyl phenyl sulfoxide
• Synonyms: Methyl phenyl sulfoxide; Methylphenyl sulphoxide; 甲基苯基亚砜

Database IDs

• CAS Number: 1193-82-4
• EC Number: 214-781-2
• MDL Number: MFCD00002088
• Beilstein Number: 1904976
• PubChem SID: 24855831; 162074395
• PubChem CID: 14516

CALCULATED PROPERTIES

• Acid pKa: 19.369268
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.70666045
• LogD (pH = 7.4): 0.70666045
• Log P: 0.70666045
• Molar Refractivity: 40.4196 cm^3
• Polarizability: 15.766749 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 26-29 °C; 26-29 °C(lit.); 26-29°C; 26-32°C
• Boiling Point: 139-140 °C/14 mmHg(lit.); 139-140°C; 93-94°C/0.3mm
• Flash Point: 186.8 °F; 86 °C; 86°C; 86°C(186°F)
• Refractive Index: 1.5775; n20/D 1.5775(lit.)

Safety Information

• Storage Warning: Hygroscopic; Irritant/Keep Cold/Hygroscopic
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 37/38-41
• Safety Statements: 26-39
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H318-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97%; ≥97.0% (GC); 98+%
• Grade: purum
• Linear Formula: CH3SOC6H5

DETAILS

Sigma Aldrich - 261696

Application
Used in the preparation of sulfoximines1 and in studies on solvent-water partitioning.2
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 68743

Other Notes
Reagent for the preparation of allylic alcohols from aldehydes and ketones1,2

REFERENCES

• Addition of the lithio-derivative to ketones followed by treatment with KO-t-Bu leads to allylic alcohols by sigmatropic rearrangement of the intermediate allyl sulfoxide: Synthesis, 640 (1980):
  
• For the fluoro-Pummerer rearrangement to fluoromethyl phenyl sulfide, see: Diethylaminosulfur trifluoride, A11992.