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159441

Sigma-Aldrich

Diethyl acetylenedicarboxylate

95%

Synonym(s):

Diethyl 2-butynedioate

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$140.40
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$340.20

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5 G
$50.80
25 G
$140.40
100 G
$340.20

About This Item

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

$50.80

Only 5 left in stockDetails
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Quality Level

100

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.)

functional group

ester

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.[1]

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

Application

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]

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

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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Certificates of Analysis (COA)

Lot/Batch Number
STBJ1754
STBH4614
STBH4613
STBB7928V
STBB7928

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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
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
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)
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