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762-21-0 - Diethyl acetylenedicarboxylate, 96% - Acetylenedicarboxylic acid diethyl ester - Butynedioic acid diethyl ester - A11719 - Alfa Aesar

A11719 Diethyl acetylenedicarboxylate, 96%

CAS Number
762-21-0
Synonyms
Acetylenedicarboxylic acid diethyl ester
Butynedioic acid diethyl ester

Size Price ($) Quantity Availability
25g 59.12
100g 185.57
500g 675.20
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Diethyl acetylenedicarboxylate, 96%

MDL
MFCD00009186
EINECS
212-095-8

Chemical Properties

Formula
CH3CH2O2CC≡CCO2CH2CH3
Formula Weight
170.16
Melting point
1-2°
Boiling Point
108-110°/11mm
Flash Point
94°(201°F)
Density
1.067
Refractive Index
1.4430
Solubility
Soluble in ethanol, ethyl ether, CCl4, Insoluble in water.

Applications

Diethyl acetylenedicarboxylate is used as a protein cross-linker. It is also used in the synthesis of 3,4,5-trisubstituted 2(5H)-furanone derivatives, highly functionalized thiazolidinone derivatives, novel cyclic peroxide glucosides and 4,11-dimesitylbisanthene, soluble bisanthene derivative, via Diels-Alder reaction.

Notes

Store at 4°C. Protect from heat. Store away from oxidizing agents. Incompatible with strong acids and strong bases.

Literature References

YW Guo; YL Shi; HB Li; M Shi. Reactions of salicyl N-tosylimines or salicylaldehydes with diethyl acetylenedicarboxylate for the synthesis of highly functionalized chromenes.Tetrahedron. 2006, 16 5875-5882.

Alan R. Katritzky; Jiangchao Yao; Weiliang Bao; Ming Qi; and Peter J. Steel. 2-Benzotriazolylaziridines and Their Reactions with Diethyl Acetylenedicarboxylate.J. Org. Chem. 1999, 64 (2), 346-350.

For reactions of acetylenedicarboxylic esters, see Dimethyl­ acetyl­enedicarboxyl­ate, A11437.

Reaction with enamines leads to 2(1H)-pyridones: Synthesis, 371 (1992).

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318

Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P363-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
743166
Hazard Class
8
Packing Group
III
Harmonized Tariff Code
2917.19
TSCA
No

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