Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

496820

Sigma-Aldrich

4-Vinyl-1,3-dioxolan-2-one

99%

Synonym(s):

VEC, Vinyl ethylene carbonate

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C5H6O3
CAS Number:
4427-96-7
Molecular Weight:
114.10
MDL number:
MFCD00143315
UNSPSC Code:
12352100
PubChem Substance ID:
24873085
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

Assay

99%

refractive index

n20/D 1.45 (lit.)

bp

237 °C/733 mmHg (lit.)

density

1.188 g/mL at 25 °C (lit.)

functional group

carbonate

storage temp.

2-8°C

SMILES string

C=CC1COC(=O)O1

InChI

1S/C5H6O3/c1-2-4-3-7-5(6)8-4/h2,4H,1,3H2

InChI key

BJWMSGRKJIOCNR-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

4-Vinyl-1,3-dioxolan-2-one (VEC) is a cyclic carbonate, that can be synthesized from acrolein by reacting with sulfur ylide and CO2.[1] The ruthenium-catalyzed transfer hydrogenation (TH) of VEC in the presence of 2-propanol forms 1,2-butanediol.[2] Indolines and indoles undergo selective C-H allylation with VEC in the presence of rhodium(III) catalyst.[3]

Application

4-Vinyl-1,3-dioxolan-2-one may be used in the preparation of 2-arylbenzo[d]thiazole scaffolds.[4]
It may be used in the synthesis of the following multi-functional cyclic carbonates:[5]
  • 4,4′-((hexane-1,6-diylbis(sulfanediyl))bis-(ethane-2,1-diyl))bis(1,3-dioxolan-2-one) (Bis-CC)
  • 2-ethyl-2-(((3-((2-(2-oxo-1,3-dioxolan-4-yl)-ethyl)thio)propanoyl)oxy) methyl)propane-1,3-diyl bis(3-((2-(2-oxo-1,3-dioxolan-4-yl)ethyl)thio)propanoate) (Tris-CC)
  • 2,2-bis(((3-((2-(2-oxo-1,3-dioxolan-4-yl)ethyl)-thio)propanoyl)oxy) methyl)propane-1,3-diyl bis(3-((2-(2-oxo-1,3-dioxolan-4-yl)ethyl)thio)propanoate) (Tetra-CC)
Used to synthesize functional polymers.[6]

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

206.4 °F - closed cup

Flash Point(C)

96.9 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCJ7938
WXBB4929V
WXBB2133V
WXBB1413V
WXBB1074V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 2

1 of 2

ETHYLENE GLYCOL BIS-(METHYL CARBONATE) AldrichCPR

S348406

ETHYLENE GLYCOL BIS-(METHYL CARBONATE)

Ethylene carbonate 98%

Sigma-Aldrich

E26258

Ethylene carbonate

Tunable poly (hydroxyl urethane) from CO2-Based intermediates using thiol-ene chemistry.
Tang CN, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 49(9, 2024-2032 (2011)
Progress in Organic Coatings, 47, 77-86 (2003)
William A Rose et al.
PloS one, 7(3), e32728-e32728 (2012-03-14)
The human vaginal microbiome plays a critical but poorly defined role in reproductive health. Vaginal microbiome alterations are associated with increased susceptibility to sexually-transmitted infections (STI) possibly due to related changes in innate defense responses from epithelial cells. Study of
Giovanna Berruti et al.
Histochemistry and cell biology, 150(2), 173-185 (2018-05-26)
Spermatids are haploid differentiating cells that, in the meantime they differentiate, translocate along the seminiferous epithelium towards the tubule lumen to be just released as spermatozoa. The success of such a migration depends on dynamic of spermatid-Sertoli cell contacts, the
Rhodium(III)-catalyzed heteroatom-directed C-H allylation with allylic phosphonates and allylic carbonates at room temperature.
Jo H, et al.
Tetrahedron, 72(4), 571-578 (2016)
View All Related Papers

Questions

1–2 of 2 Questions  

  1. 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

      Helpful?

  2. 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

      Helpful?

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service