159441
Diethyl acetylenedicarboxylate
95%
Synonym(s):
Diethyl 2-butynedioate
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About This Item
Linear Formula:
C2H5OCOC≡CCOOC2H5
CAS Number:
Molecular Weight:
170.16
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
212-095-8
Beilstein/REAXYS Number:
743166
MDL number:
Assay:
95%
Form:
liquid
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.)
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
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.
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
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signalword
Danger
hcodes
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
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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)
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.