(ethenesulfonyl)ethene

• ChemBase ID: 9852
• Molecular Formular: C4H6O2S
• Molecular Mass: 118.15424
• Monoisotopic Mass: 118.00885043
• SMILES: S(=O)(=O)(C=C)C=C
• Canonical SMILES: C=CS(=O)(=O)C=C
• InChI: InChI=1S/C4H6O2S/c1-3-7(5,6)4-2/h3-4H,1-2H2
• InChIKey: AFOSIXZFDONLBT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (ethenesulfonyl)ethene
• IUPAC Traditional name: vinyl sulfone
• Synonyms: Divinyl sulfone; Diethenyl sulphone; Divinyl sulphone; Vinyl sulfone; Divinyl sulfone; (vinylsulfonyl)ethene; 乙烯砜; 二乙烯基砜

Database IDs

• CAS Number: 77-77-0
• EC Number: 201-057-6
• MDL Number: MFCD00008623
• Beilstein Number: 1071329
• PubChem SID: 24867488; 160973159; 24900744
• PubChem CID: 6496

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.163724
• LogD (pH = 7.4): 0.163724
• Log P: 0.163724
• Molar Refractivity: 27.6062 cm^3
• Polarizability: 11.80689 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -26 °C(lit.); -26°C; ca -26°C
• Boiling Point: 233-234°C; 233-234°C; 234 °C(lit.)
• Flash Point: 102 °C; 102°C; 102°C(215°F); 215.6 °F; 216 °F
• Density: 1.0177; 1.177; 1.177 g/mL at 25 °C(lit.)
• Refractive Index: 1.476; 1.4760; n20/D 1.476(lit.); n20/D 1.477

Safety Information

• Storage Warning: TOXIC, CORROSIVE; Very Toxic/Irritant/Corrosive/Carcinogenic/Light Sensitive/Keep Cold
• RTECS: KM7175000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2810; UN2927
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1; I
• Risk Statements: 25-27-34; 25-27-36/37/38
• Safety Statements: 20-23-26-27/28-36/37/39-45-60; 26-28.1-36/37-45; 26-28-36/37-45
• TSCA Listed: false; 否
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300 + H310-H315-H318-H335; H300-H310-H314-H318
• GHS Precautionary statements: P261-P264-P280-P301 + P310-P302 + P350-P305 + P351 + P338; P280-P262-P305+P351+P338-P309-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2810 6.1/PG 1
• Storage Temperature: 2-8°C

Pharmacology Properties

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

Product Information

• Purity: ≥98.0% (GC); 97%; 97%, stab. with 0.05% hydroquinone; 98%
• Grade: purum
• Contains: ~0.05% hydroquinone as stabilizer; <650 ppm hydroquinone as inhibitor
• Linear Formula: (CH2=CH)2SO2

DETAILS

Apollo Scientific Ltd - OR10898

Stabilised with hydroquinone

Sigma Aldrich - V3700

Packaging
5, 25, 100 g in glass bottle

REFERENCES

• Reactive dienophile and Michael acceptor. Reacts with oximes to give bicyclic products derived from dipolar cycloaddition of a transient nitrone intermediate: Tetrahedron Lett., 29, 2417 (1988):
  
• In the presence of thiazolium salt catalysts (see 3-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride, L08750), the Stetter reaction with aldehydes gives 1,4-diketones by loss of SO₂ from the intermediate dialkyl sulfone: Chem. Ber., 114, 1226 (1981); for a related example, see Phenyl vinyl sulfone, A14794. Cyclization of the 1,4-diones derived from pyrrole-, furan- and thiophene-2-carboxaldehydes provides a route to polypyrroles and analogues as potential porphyrin-type subunits: J. Org. Chem., 55, 2904 (1990).