Diethyl acetylenedicarboxylate

Diethyl acetylenedicarboxylate Basic information
Product Name:Diethyl acetylenedicarboxylate
Synonyms:Bis-(Ethoxycarbonyl)acetylene;Diethyl 2-butynedioate;butynedioic acid diethyl ester;YL2-BUTYNEDIOATE;Diethyl but-2-yne-1,4-dioate;DIETHYL ACETYLENEDICARBOXYLATE;DIETHYL BUTYNEDIOATE;2-butynedioic acid diethyl ester
CAS:762-21-0
MF:C8H10O4
MW:170.16
EINECS:212-095-8
Product Categories:Aromatic Esters;Miscellaneous;Acetylenes;Acetylenic Carboxylic Acids & Their Derivatives;bc0001
Mol File:762-21-0.mol
Diethyl acetylenedicarboxylate Structure
Diethyl acetylenedicarboxylate Chemical Properties
Melting point 1-3 °C
Boiling point 107-110 °C11 mm Hg(lit.)
density 1.063 g/mL at 25 °C(lit.)
refractive index n20/D 1.443(lit.)
Fp 202 °F
storage temp. 2-8°C
form Liquid
color Clear light yellow
Specific Gravity1.063
Water Solubility Soluble in ethanol, ethyl ether, CCl4, Insoluble in water.
BRN 743166
CAS DataBase Reference762-21-0(CAS DataBase Reference)
NIST Chemistry ReferenceDiethylacetylene dicarboxylate(762-21-0)
Safety Information
Hazard Codes C
Risk Statements 34
Safety Statements 26-36/37/39-45-25
RIDADR UN 3265 8/PG 2
WGK Germany 3
8-10
HazardClass 8
PackingGroup III
HS Code 29171990
MSDS Information
ProviderLanguage
2-Butynedioic acid diethyl ester English
SigmaAldrich English
ACROS English
ALFA English
Diethyl acetylenedicarboxylate Usage And Synthesis
Chemical PropertiesDiethyl acetylenedicarboxylate is a clear light yellow liquid which has a disagreeable smell. It is a cheap and readily available material in industry. The triple bond is a critical and useful functional group, and it has extensive applications in organic synthesis. It can react with amines, aldehydes, ketones, etc. Therefore it can be used to form various heterocycles.
Synthesis of diethyl acetylenedicarboxylate
Synthesis of diethyl acetylenedicarboxylate
UsesDiethyl 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.
UsesDiethyl 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 DescriptionDiethyl acetylenedicarboxylate is a protein cross-linker.
Purification MethodsDissolve the ester in *C6H6, wash it with NaHCO3, H2O, dry over Na2SO4, filter, evaporate and distil it in a vacuum [IR: Walton & Hughes J Am Chem Soc 79 3985 1957, Truce & Kruse J Am Chem Soc 81 5372 1959]. [Beilstein 2 H 803.]
Acetylenedicarboxylic acid DI-TERT-BUTYL ACETYLENEDICARBOXYLATE Diethyl adipate Methyl propiolate Ethyl pyruvate Propargyl alcohol PENTAACETYL-5-THIOGLUCOSE PROPYNAL 2-Butyne-1,4-diol Diethyl ether (2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester Propiolic Acid METHYL PROPARGYL ETHER Diethyl pimelate Diethyl acetylenedicarboxylate 2-Butyn-1-ol Diethyl carbonate AcidEster

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