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Merck
CN

159441

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24849816
EC Number:
212-095-8
Beilstein/REAXYS Number:
743166
MDL number:
MFCD00009186

Key Documents

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Product Name

Diethyl acetylenedicarboxylate, 95%

InChI key

STRNXFOUBFLVIN-UHFFFAOYSA-N

InChI

1S/C8H10O4/c1-3-11-7(9)5-6-8(10)12-4-2/h3-4H2,1-2H3

SMILES string

CCOC(=O)C#CC(=O)OCC

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

Quality Level

100

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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

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.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
STBJ1754
STBH4614
STBH4613
STBB7928V
STBB7928

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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
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
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
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