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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/REAXYS Number:
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

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

233.6 °F - closed cup

flash_point_c

112 °C - closed cup

ppe

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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1,3-Butadiene ≥99%

Sigma-Aldrich

295035

1,3-Butadiene

Sulfolane 99%

Sigma-Aldrich

T22209

Sulfolane

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)
Switchable butadiene sulfone pretreatment of Miscanthus in the presence of water
J Atilio De, et al.
Green Chemistry, 15, 1067-1078 (2013)
Monika Johansson et al.
Journal of pharmaceutical and biomedical analysis, 100, 215-229 (2014-08-30)
An effective screening procedure to identify and quantify active pharmaceutical substances in suspected illegal medicinal products is described. The analytical platform, consisting of accurate mass determination with liquid chromatography time-of-flight mass spectrometry (LC-QTOF-MS) in combination with nuclear magnetic resonance (NMR)

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