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159441

Sigma-Aldrich

Diethyl acetylenedicarboxylate

95%

Sinonimo/i:

Diethyl 2-butynedioate

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About This Item

Formula condensata:
C2H5OCOC≡CCOOC2H5
Numero CAS:
762-21-0
Peso molecolare:
170.16
Beilstein:
743166
Numero CE:
212-095-8
Numero MDL:
MFCD00009186
Codice UNSPSC:
12352100
ID PubChem:
24849816
NACRES:
NA.22
Prezzi e disponibilità al momento non sono disponibili

Livello qualitativo

100

Saggio

95%

Stato

liquid

Indice di rifrazione

n20/D 1.443 (lit.)

P. ebollizione

107-110 °C/11 mmHg (lit.)

Densità

1.063 g/mL at 25 °C (lit.)

Gruppo funzionale

ester

Temperatura di conservazione

2-8°C

Stringa SMILE

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
STRNXFOUBFLVIN-UHFFFAOYSA-N

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Categorie correlate

Descrizione generale

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]

Applicazioni

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]

Pittogrammi

Corrosion
GHS05

Avvertenze

Danger

Indicazioni di pericolo

H314

Classi di pericolo

Skin Corr. 1B

Codice della classe di stoccaggio

8A - Combustible corrosive hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

201.2 °F - closed cup

Punto d’infiammabilità (°C)

94 °C - closed cup

Dispositivi di protezione individuale

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

Scegli una delle versioni più recenti:

Certificati d'analisi (COA)

Lot/Batch Number
STBJ1754
STBH4614
STBH4613
STBB7928V
STBB7928

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Sigma-Aldrich

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Ethyl phenylpropiolate 98%

Sigma-Aldrich

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Ethyl phenylpropiolate

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
Microwave Induced Stereoselective Synthesis of O--Vinyl Oximes using Acetylenic Esters as Efficient Michael Acceptors
Ankush M et al.
ChemistrySelect, 3, 9464-9468 (2018)
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.
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
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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

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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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