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Merck

159441

Sigma-Aldrich

Diethyl acetylenedicarboxylate

95%

Synonim(y):

Diethyl 2-butynedioate

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5 G
128,00 zł
25 G
392,00 zł
100 G
1267,00 zł

About This Item

Wzór liniowy:
C2H5OCOC≡CCOOC2H5
Numer CAS:
Masa cząsteczkowa:
170.16
Beilstein:
743166
Numer WE:
Numer MDL:
Kod UNSPSC:
12352100
Identyfikator substancji w PubChem:
NACRES:
NA.22

128,00 zł


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Poziom jakości

Próba

95%

Formularz

liquid

współczynnik refrakcji

n20/D 1.443 (lit.)

bp

107-110 °C/11 mmHg (lit.)

gęstość

1.063 g/mL at 25 °C (lit.)

grupa funkcyjna

ester

temp. przechowywania

2-8°C

ciąg 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

Klucz InChI

STRNXFOUBFLVIN-UHFFFAOYSA-N

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Opis ogólny

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]

Zastosowanie

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]
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Piktogramy

Corrosion

Hasło ostrzegawcze

Danger

Zwroty wskazujące rodzaj zagrożenia

Klasyfikacja zagrożeń

Skin Corr. 1B

Kod klasy składowania

8A - Combustible corrosive hazardous materials

Klasa zagrożenia wodnego (WGK)

WGK 3

Temperatura zapłonu (°F)

201.2 °F - closed cup

Temperatura zapłonu (°C)

94 °C - closed cup

Środki ochrony indywidualnej

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


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Klienci oglądali również te produkty

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.
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
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
W M Basyouni et al.
Drug research, 65(9), 473-478 (2014-09-11)
A series of 3,4,5-trisubstituted 2(5H)-furanone derivatives was synthesized through one-pot reaction of amines, aldehydes and diethyl acetylenedicarboxylate. Silica sulfuric acid efficiently catalyzes the 3-component reaction to afford the corresponding 2(5H)-furanones in high yields. The synthesized compounds were tested against HEPG2

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    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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