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159441

Sigma-Aldrich

Diethyl acetylenedicarboxylate

95%

Synonym(s):

Diethyl 2-butynedioate

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About This Item

Linear Formula:
C2H5OCOC≡CCOOC2H5
CAS Number:
762-21-0
Molecular Weight:
170.16
Beilstein:
743166
EC Number:
212-095-8
MDL number:
MFCD00009186
UNSPSC Code:
12352100
PubChem Substance ID:
24849816
NACRES:
NA.22

Assay

95%

form

liquid

refractive index

n20/D 1.443 (lit.)

bp

107-110 °C/11 mmHg (lit.)

density

1.063 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

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

InChI key

STRNXFOUBFLVIN-UHFFFAOYSA-N

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General description

Diethyl acetylenedicarboxylate is a protein cross-linker.

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

Application

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

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

201.2 °F - closed cup

Flash Point(C)

94 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

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Sigma-Aldrich

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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
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.
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
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)
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