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.)

Flash point:

202 °F

storage temp. 

2-8°C

form 

Liquid

Specific Gravity

1.063

color 

Clear light yellow

Water Solubility 

Soluble in ethanol, ethyl ether, CCl4, Insoluble in water.

BRN 

743166

InChI

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

InChIKey

STRNXFOUBFLVIN-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

762-21-0(CAS DataBase Reference)

NIST Chemistry Reference

Diethylacetylene 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

F 

8-10

HazardClass 

8

PackingGroup 

III

HS Code 

29171990

MSDS

• Language:English Provider:2-Butynedioic acid diethyl ester
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Diethyl acetylenedicarboxylate Usage And Synthesis

Chemical Properties

Diethyl 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

Uses

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.

Uses

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.

Synthesis

1. In a 250 mL round-bottomed flask, ethanol (1.2 g, 26 mmol), butynedioic acid (1 g, 8.77 mmol), p-toluenesulfonic acid (30 mg, 0.17 mmol), and 1,2-dichloroethane (50 mL) were added sequentially, and refluxed with heat for 12 h. 2. After the reaction was completed, toluene (50 mL, with moisture trap) was added to the reaction system, and refluxed for 8 h. 3. reflux for 8 h. 3. The reaction solution was concentrated and purified by fast column chromatography (eluent: petroleum ether/ethyl acetate = 98/2) to give purified diethyl butynedioate (1.35 g, 91% yield).

Purification Methods

Dissolve 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.]

References

[1] Patent: CN103483194, 2016, B. Location in patent: Paragraph 0045
[2] European Journal of Organic Chemistry, 2015, vol. 2015, # 20, p. 4519 - 4523
[3] Journal fuer Praktische Chemie (Leipzig), 1892, vol. <2>46, p. 209
[4] Journal fuer Praktische Chemie (Leipzig), 1895, vol. <2>52, p. 289,326,359,
[5] Chemische Berichte, 1885, vol. 18, p. 2271

Diethyl acetylenedicarboxylate(762-21-0)Related Product Information

• 2-Butyne-1,4-diol
• (2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester
• Mefenpyr-diethyl
• Triethyl citrate
• Diethyl adipate
• Ethyl pyruvate
• Diethyl pimelate
• Acetylenedicarboxylic acid
• Diethyl carbonate
• Diethyl methylmalonate
• Ethyl glyoxalate
• Diethyl oxalate
• Diethyl maleate
• Diethyl succinate
• Diethyl malonate
• Tris(trimethylsilyl)phosphate
• Diethyl oxalacetate
• Diethyl phthalate