3-Sulfolene

• Catalog No.: A13887
• CAS Number: 77-79-2
• M. F.: C4H6O2S
• M. W.: 118.15424
• Purity: 98%

SYNONYMS

• Title: 环丁烯砜
• IUPAC name: 2,5-dihydro-1λ^6-thiophene-1,1-dione
• IUPAC Traditional name: sulfolene
• Synonyms: Butadiene sulfone; 2,5-Dihydrothiophene-1,1-dioxide

DATABASE IDS

• MDL Number: MFCD00005481
• Beilstein Number: 107004
• EC Number: 201-059-7
• CAS Number: 77-79-2
• Merck Index: 148956

PROPERTIES

• Purity: 98%
• Density: 1.314
• Flash Point: 112°C(233°F)
• Melting Point: 63-67°C
• GHS Hazard statements: H318
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P280-P305+P351+P338-P310
• Risk Statements: 41
• RTECS: XM9100000
• Safety Statements: 26-39
• TSCA Listed: 是

REFERENCES

• Convenient crystalline source of 1,3-butadiene, which is generated on heating to about 110^oC: Rec. Trav. Chim., 61, 785 (1942). For an example of its use in the Diels-Alder reaction, see: Org. Synth. Coll., 6, 454 (1988).
• Also behaves as a dienophile in with reactive dienes, for example 1,3-Diphenylisobenzofuran, L00101: J. Org. Chem., 34, 538 (1969).
• In the presence of Pd(OAc)₂, couples with aryldiazonium fluoroborates to give 3-aryl-4-sulfolenes which are readily isomerized with triethylamine to the 3-aryl-3-sulfolenes, providing a source of the corresponding 2-arylbutadienes: Synth. Commun., 26, 231 (1996).
• Lithiation occurs at the 2-position; subsequent alkylation and thermal extrusion of SO₂ gave a polyene intermediate in a synthesis of the taxane ring system: J. Org. Chem., 62, 2957 (1997).