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496820

Sigma-Aldrich

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

99%

Sinónimos:

VEC, Vinyl ethylene carbonate

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About This Item

Fórmula empírica (notación de Hill):
C5H6O3
Número de CAS:
4427-96-7
Peso molecular:
114.10
Número MDL:
MFCD00143315
Código UNSPSC:
12352100
ID de la sustancia en PubChem:
24873085
NACRES:
NA.22
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Nivel de calidad

100

Ensayo

99%

índice de refracción

n20/D 1.45 (lit.)

bp

237 °C/733 mmHg (lit.)

densidad

1.188 g/mL at 25 °C (lit.)

grupo funcional

carbonate

temp. de almacenamiento

2-8°C

cadena SMILES

C=CC1COC(=O)O1

InChI

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

Clave InChI

BJWMSGRKJIOCNR-UHFFFAOYSA-N

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Descripción general

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]

Aplicación

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]

Pictogramas

Skull and crossbones
GHS06

Palabra de señalización

Danger

Frases de peligro

H301

Clasificaciones de peligro

Acute Tox. 3 Oral

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 1

Punto de inflamabilidad (°F)

206.4 °F - closed cup

Punto de inflamabilidad (°C)

96.9 °C - closed cup

Equipo de protección personal

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificados de análisis (COA)

Lot/Batch Number
BCCJ7938
WXBB4929V
WXBB2133V
WXBB1413V
WXBB1074V

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ETHYLENE GLYCOL BIS-(METHYL CARBONATE)

Ethylene carbonate 98%

Sigma-Aldrich

E26258

Ethylene carbonate

Rhodium-catalyzed mild and selective C-H allylation of indolines and indoles with 4-vinyl-1,3-dioxolan-2-one: facile access to indolic scaffolds with an allylic alcohol moiety.
Sharma S, et al.
Tetrahedron, 71(16), 2435-2441 (2015)
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Co-culture of bone marrow stromal cells (BMSCs) and vascular endothelial cells (VECs) is a promising strategy for better osteogenesis and pre-vascularization in bone tissue engineering. Recent reports have shown that mechanical stretching further promotes osteogenesis in BMSC/VEC co-culture systems, but
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  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

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  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

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