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V3700

Sigma-Aldrich

Divinyl sulfone

contains hydroquinone as inhibitor, ≥96%

Synonym(s):

Vinyl sulfone

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5 G
¥8,540
25 G
¥22,200
100 G
¥71,300

About This Item

Linear Formula:
(CH2=CH)2SO2
CAS Number:
77-77-0
Molecular Weight:
118.15
Beilstein:
1071329
EC Number:
201-057-6
MDL number:
MFCD00008623
UNSPSC Code:
12162002
PubChem Substance ID:
24900744
NACRES:
NA.23

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Quality Level

200

Assay

≥96%

contains

hydroquinone as inhibitor

refractive index

n20/D 1.476 (lit.)

bp

234 °C (lit.)

mp

−26 °C (lit.)

density

1.177 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C=CS(=O)(=O)C=C

InChI

1S/C4H6O2S/c1-3-7(5,6)4-2/h3-4H,1-2H2

InChI key

AFOSIXZFDONLBT-UHFFFAOYSA-N

Gene Information

human ... LOC129293(129293)

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General description

Divinyl sulfone is a highly reactive chemical compound due to the presence of two vinyl groups, which make it an effective cross-linking agent and bifunctional reactive compound. It is used in the production of hydrogels, resins, and other polymeric materials. The resulting cross-linked polymers exhibit enhanced mechanical strength, stability, and insolubility in solvents.

Application

Divinyl sulfone can be used as:
  • A cross-linking agent to synthesize divinyl sulfone-crosslinked hyaluronic acid hydrogels for specific biomedical applications, such as tissue engineering or drug delivery.
  • A cross-linking agent to develop the conducting polymer film with MXene layers. This crosslinking can enhance the mechanical properties and stability of the composite film.
Hyaluronic acid (HA) crosslinked with DVS forms hydrogels.
DVS and its mono and di-substituted derivatives are useful starting materials in the preparation of thiomorpholine 1,1-dioxides and other synthetically important macro- and the heterocycles.
DVS may be used to shrink proofing cotton by crosslinking it with cellulose.

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

215.6 °F - closed cup

Flash Point(C)

102 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

V3700-25G:
V3700-100G:
V3700-PM:
V3700-5G:
V3700-VAR:
V3700-10KG:
V3700-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX5631
MKCX5296
MKCX0723
MKCX0403
MKCW1879

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Tobias Käppler et al.
Biotechnology and bioengineering, 102(2), 535-545 (2008-08-30)
A new approach for in situ product removal from bioreactors is presented in which high-gradient magnetic separation is used. This separation process was used for the adsorptive removal of proteases secreted by Bacillus licheniformis. Small, non-porous bacitracin linked magnetic adsorbents
Stereocontrolled creation of all-carbon quaternary stereocenters by organocatalytic conjugate addition of oxindoles to vinyl sulfone.
Qiang Zhu et al.
Angewandte Chemie (International ed. in English), 49(42), 7753-7756 (2010-09-08)
Nagarathanam Veerasamy et al.
Organic letters, 14(6), 1596-1599 (2012-03-01)
An efficient enantioselective synthesis of cermizine D has been developed that exploits the use of a common intermediate to access over 85% of the carbon backbone. Key steps include an organocatalyzed heteroatom Michael addition, a diastereoselective alkylation with α-iodomethyl phenyl
Peng Zhao et al.
Organic letters, 15(2), 402-405 (2013-01-11)
An intramolecular pyrone Diels-Alder reaction-elimination retro-Diels-Alder cascade of a vinyl sulfone was used in the synthesis of cavicularin, a molecule possessing conformational chirality. The vinyl sulfone substitution pattern allowed for regiocontrol in the Diels-Alder cascade event.
Cátia Teixeira et al.
Journal of computer-aided molecular design, 25(8), 763-775 (2011-07-26)
Comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) based on three-dimensional quantitative structure-activity relationship (3D-QSAR) studies were conducted on a series (39 molecules) of peptidyl vinyl sulfone derivatives as potential Plasmodium Falciparum cysteine proteases inhibitors. Two
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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