(ethenesulfonyl)benzene

• ChemBase ID: 70033
• Molecular Formular: C8H8O2S
• Molecular Mass: 168.21292
• Monoisotopic Mass: 168.0245005
• SMILES: S(=O)(=O)(C=C)c1ccccc1
• Canonical SMILES: C=CS(=O)(=O)c1ccccc1
• InChI: InChI=1S/C8H8O2S/c1-2-11(9,10)8-6-4-3-5-7-8/h2-7H,1H2
• InChIKey: UJTPZISIAWDGFF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (ethenesulfonyl)benzene
• IUPAC Traditional name: (ethenesulfonyl)benzene
• Synonyms: Phenyl vinyl sulfone; (ethenesulfonyl)benzene; Phenyl vinyl sulfone; 苯基乙烯基砜

Database IDs

• CAS Number: 5535-48-8
• EC Number: 226-890-2
• MDL Number: MFCD00007554
• Beilstein Number: 1906894
• PubChem SID: 24854323; 24887440; 162035758; 24887439
• PubChem CID: 79664

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.5459023
• LogD (pH = 7.4): 1.5459023
• Log P: 1.5459023
• Molar Refractivity: 43.5982 cm^3
• Polarizability: 17.903816 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 67-69 °C(lit.); 67-71°C; 68 - 70°C; 68-70 °C
• Hydrophobicity(logP): 0.746

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-37/38-41-43; 36/37/38-43
• Safety Statements: 24-26-37; 26-36/37/39
• TSCA Listed: false; 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H315-H317-H318-H335; H315-H319-H317-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P280G-P262-P305+P351+P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Gene Information: human ... LOC129293(129293)

Product Information

• Purity: ≥98.0% (GC); ≥99.0% (GC); 95%; 95+%; 97%; 98%; 99%; 99+%
• Grade: puriss.; purum
• Ignition Residue: ≤0.2%
• Linear Formula: C6H5SO2CH=CH2

DETAILS

Sigma Aldrich - 241717

Packaging
1, 5 g in glass bottle
Application
Common reagent used in a variety of cycloaddition reactions to form cyclopropanes,1 cyclohexenes,2,3 and cyclooctadienes.4

Sigma Aldrich - 79293

Other Notes
Dienophile; adducts can conveniently be transformed into alkanes or ketones (equivalent of ethylene or ketene), review1

REFERENCES

• Reactive dienophile. Can function as an acetylene equivalent if benzenesulfinic acid is eliminated thermally from the Diels-Alder adduct to form an olefinic double bond: J. Am. Chem. Soc., 100, 1597 (1978).
• Can also behave as an activated form of ethylene if the sulfone group is cleaved from the adduct, e.g. with Na amalgam, with the possibility of prior alkylation of the adduct: J. Org. Chem., 48, 4976 (1983):
  
• For addition to 1-Methoxy-3-trimethylsiloxy-1,3-butadiene, L06100, see: J. Org. Chem., 48, 4986 (1983). Addition to steroids with a cyclopentadienoid D-ring, followed by cleavage of the resulting alkene, gives the diformyl derivatives, useful for further functionalization: J. Chem. Soc., Perkin 1, 241 (1990).
• Undergoes the Baylis-Hillman reaction (addition to aldehydes in the presence of 1,4-Diazabicyclo[2.2.2]octane, A14003): Tetrahedron, 44, 6095 (1988).
• For use in a 1,3-dipolar cycloaddition reaction, see 3-Hydroxypyridine, A13910.
• See also Divinyl sulfone, L12827.