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159441

Sigma-Aldrich

Diethyl acetylenedicarboxylate

95%

Sinónimos:

Diethyl 2-butynedioate

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About This Item

Fórmula lineal:
C2H5OCOC≡CCOOC2H5
Número de CAS:
762-21-0
Peso molecular:
170.16
Beilstein:
743166
Número CE:
212-095-8
Número MDL:
MFCD00009186
Código UNSPSC:
12352100
ID de la sustancia en PubChem:
24849816
NACRES:
NA.22
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Ensayo

95%

Formulario

liquid

índice de refracción

n20/D 1.443 (lit.)

bp

107-110 °C/11 mmHg (lit.)

densidad

1.063 g/mL at 25 °C (lit.)

grupo funcional

ester

temp. de almacenamiento

2-8°C

cadena SMILES

CCOC(=O)C#CC(=O)OCC

InChI

1S/C8H10O4/c1-3-11-7(9)5-6-8(10)12-4-2/h3-4H2,1-2H3

Clave InChI

STRNXFOUBFLVIN-UHFFFAOYSA-N

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Descripción general

Diethyl acetylenedicarboxylate is a protein cross-linker.[1]

Diethyl acetylenedicarboxylate is used as a Michael acceptor for O-vinyl oximes synthesis, and is used in the nucleophilic addition reaction.[2] [3]

Aplicación

Diethyl acetylenedicarboxylate was used in the synthesis of:
  • 3,4,5-trisubstituted 2(5H)-furanone derivatives[4]
  • highly functionalized thiazolidinone derivatives[5]
  • novel cyclic peroxide glucosides[6]
  • 4,11-dimesitylbisanthene, soluble bisanthene derivative, via Diels-Alder reaction[7]

Pictogramas

Corrosion
GHS05

Palabra de señalización

Danger

Frases de peligro

H314

Clasificaciones de peligro

Skin Corr. 1B

Código de clase de almacenamiento

8A - Combustible corrosive hazardous materials

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

201.2 °F - closed cup

Punto de inflamabilidad (°C)

94 °C - closed cup

Equipo de protección personal

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

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Certificados de análisis (COA)

Lot/Batch Number
STBJ1754
STBH4614
STBH4613
STBB7928V
STBB7928

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Microwave Induced Stereoselective Synthesis of O--Vinyl Oximes using Acetylenic Esters as Efficient Michael Acceptors
Ankush M et al.
ChemistrySelect, 3, 9464-9468 (2018)
Eric H Fort et al.
Journal of the American Chemical Society, 131(44), 16006-16007 (2009-10-17)
A soluble bisanthene derivative, 4,11-dimesitylbisanthene, has been synthesized in three steps from bianthrone. In hot toluene, this bisanthene undergoes a clean Diels-Alder reaction with diethyl acetylenedicarboxylate to give a rearomatized 1:1 cycloadduct and, more slowly, a rearomatized 2:1 cycloadduct. In
Abdelmadjid Benmohammed et al.
Molecules (Basel, Switzerland), 19(3), 3068-3083 (2014-03-13)
We present herein the synthesis in good yields of two series of highly functionalized thiazolidinone derivatives from the reactions of various 4-phenyl-3-thio-semicarbazones with ethyl 2-bromoacetate and diethyl acetylenedicarboxylate, respectively.
Synthesis of pyrrolidinone derivatives from aniline, an aldehyde and diethyl acetylenedicarboxylate in an ethanolic citric acid solution under ultrasound irradiation
Hamideh A et al.
Green Chemistry, 18, 3582-3593 (2016)
Di-Zao Li et al.
Journal of Asian natural products research, 11(7), 613-620 (2010-02-26)
Four novel cyclic peroxide glucosides 15a, 15b, 16a, and 16b, optically pure analogs of shuangkangsu (1), which is an anti-virus natural product with an unusual skeleton isolated from the buds of Lonicera japonica Thunb, were first synthesized totally in six
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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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