| Identification | More | [Name]
Diethyl acetylenedicarboxylate | [CAS]
762-21-0 | [Synonyms]
2-butynedioic acid diethyl ester
ACETYLENEDICARBOXYLIC ACID DIETHYL ESTER
DIETHYL ACETYLENEDICARBOXYLATE
DIETHYL BUTYNEDIOATE
Bis-(Ethoxycarbonyl)acetylene
Diethyl 2-butynedioate
butynedioic acid diethyl ester
but-2-ynedioic acid diethyl ester
YL2-BUTYNEDIOATE
Diethyl but-2-yne-1,4-dioate
Bis(carboethoxy)acetylene
Diethyl acetylenedicarboxylic acid | [EINECS(EC#)]
212-095-8 | [Molecular Formula]
C8H10O4 | [MDL Number]
MFCD00009186 | [Molecular Weight]
170.16 | [MOL File]
762-21-0.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR LIGHT YELLOW LIQUID | [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. ]
0-6°C | [form ]
Liquid | [color ]
Clear light yellow | [Specific Gravity]
1.063 | [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 Data | Back Directory | [Symbol(GHS) ]
GHS05 | [Signal word ]
Danger | [Hazard statements ]
H314 | [Precautionary statements ]
P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363-P405 | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S25:Avoid contact with eyes . | [RIDADR ]
UN 3265 8/PG 2
| [WGK Germany ]
3
| [F ]
8-10 | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29171990 | [Storage Class]
8A - Combustible corrosive hazardous materials | [Hazard Classifications]
Skin Corr. 1B |
| Hazard Information | Back Directory | [Chemical Properties]
CLEAR LIGHT YELLOW LIQUID | [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. | [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 |
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