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159441

Sigma-Aldrich

Diethyl acetylenedicarboxylate

95%

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Synonym(s):
Diethyl 2-butynedioate
Linear Formula:
C2H5OCOC≡CCOOC2H5
CAS Number:
Molecular Weight:
170.16
Beilstein/REAXYS Number:
743166
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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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This Item
D138401270822341371
Diethyl acetylenedicarboxylate 95%

159441

Diethyl acetylenedicarboxylate

Dimethyl acetylenedicarboxylate 95%

D138401

Dimethyl acetylenedicarboxylate

Diethyl succinate-2,2,3,3-d4 98 atom % D

341371

Diethyl succinate-2,2,3,3-d4

Quality Level

100

Quality Level

200

Quality Level

-

Quality Level

-

refractive index

n20/D 1.443 (lit.)

refractive index

n20/D 1.447 (lit.)

refractive index

-

refractive index

n20/D 1.419 (lit.)

density

1.063 g/mL at 25 °C (lit.)

density

1.156 g/mL at 25 °C (lit.)

density

-

density

1.050 g/mL at 25 °C

bp

107-110 °C/11 mmHg (lit.)

bp

95-98 °C/19 mmHg (lit.)

bp

80-82 °C/0.05 mmHg (lit.)

bp

218 °C (lit.)

form

liquid

form

liquid

form

solid

form

-

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

signalword

Danger

hcodes

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible, corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

201.2 °F - closed cup

flash_point_c

94 °C - closed cup

ppe

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


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Customers Also Viewed

Slide 1 of 4

1 of 4

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