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B84505

Sigma-Aldrich

Butadiene sulfone

98%

Synonym(s):

2,5-Dihydrothiophene-1,1-dioxide, 3-Sulfolene

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About This Item

Empirical Formula (Hill Notation):
C4H6O2S
CAS Number:
77-79-2
Molecular Weight:
118.15
Beilstein:
107004
EC Number:
201-059-7
MDL number:
MFCD00005481
UNSPSC Code:
12352100
PubChem Substance ID:
24892071
NACRES:
NA.22

Assay

98%

form

crystals

mp

65-66 °C (lit.)

SMILES string

O=S1(=O)CC=CC1

InChI

1S/C4H6O2S/c5-7(6)3-1-2-4-7/h1-2H,3-4H2

InChI key

MBDNRNMVTZADMQ-UHFFFAOYSA-N

General description

Butadiene sulfone is a β, γ-unsaturated cyclic sulfone that can switch from solvent to 1,3-butadiene and sulfur dioxide in the presence of water. It is commonly used as a building block especially in the synthesis of functionalized dienes, through alkylation, deprotonation, and cheletropic SO2 removal.

Application

  • Stretchable PEDOT:PSS/Li-TFSI/XSB Composite Films: Butadiene sulfone plays a critical role in the synthesis of composite films designed for electromagnetic interference shielding, indicating its potential in the production of advanced electronic materials and contributing to the development of stretchable electronics (Jiang et al., 2023).
  • Applications of 3D printed bone tissue engineering scaffolds: Research underscores the versatility of butadiene sulfone as a solvent in the 3D printing of bone tissue scaffolds, emphasizing its utility in regenerative medicine and the manufacturing of biocompatible engineering materials (Su et al., 2021).
  • Zwitterionic phosphonium ligands: The study highlights the synthesis and application of zwitterionic phosphonium ligands using butadiene sulfone, showcasing its efficacy in the telomerization process of 1,3-butadiene, which is essential for the production of specialty chemicals (Pews-Davtyan et al., 2016).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

233.6 °F - closed cup

Flash Point(C)

112 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Switchable butadiene sulfone pretreatment of Miscanthus in the presence of water
J Atilio De, et al.
Green Chemistry, 15, 1067-1078 (2013)
Tandem vinylogous 1, 2-addition/anionic oxy-Cope reaction leading from butadiene sulfone to an orthogonally functionalized bicycle
Michael B G, et al.
The Journal of Organic Chemistry, 75, 6312-6315 (2010)
Monika Johansson et al.
Journal of pharmaceutical and biomedical analysis, 100, 215-229 (2014-08-30)
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