Diethyl acetylenedicarboxylate
- Product Name
- Diethyl acetylenedicarboxylate
- CAS No.
- 762-21-0
- Chemical Name
- Diethyl acetylenedicarboxylate
- Synonyms
- Diethyl but-2-ynedioate;DIETHYL BUTYNEDIOATE;Diethyl 2-butynedioate;YL2-BUTYNEDIOATE;Diethyl butyrate;Diethyl acetylenedic;diethylbut-2-indioat;Bis(carboethoxy)acetylene;Diethyl but-2-yne-1,4-dioate;Bis-(Ethoxycarbonyl)acetylene
- CBNumber
- CB8456726
- Molecular Formula
- C8H10O4
- Formula Weight
- 170.16
- MOL File
- 762-21-0.mol
Diethyl acetylenedicarboxylate Property
- 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
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H314Causes severe skin burns and eye damage
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P363Wash contaminated clothing before reuse.
P405Store locked up.
N-Bromosuccinimide Price
- Product number
- 159441
- Product name
- Diethyl acetylenedicarboxylate
- Purity
- 95%
- Packaging
- 5g
- Price
- $50.8
- Updated
- 2025/07/31
- Product number
- 159441
- Product name
- Diethyl acetylenedicarboxylate
- Purity
- 95%
- Packaging
- 25g
- Price
- $109.2
- Updated
- 2025/07/31
- Product number
- A0089
- Product name
- Diethyl Acetylenedicarboxylate
- Purity
- >96.0%(GC)
- Packaging
- 25mL
- Price
- $98
- Updated
- 2025/07/31
- Product number
- A0089
- Product name
- Diethyl Acetylenedicarboxylate
- Purity
- >96.0%(GC)
- Packaging
- 250mL
- Price
- $734
- Updated
- 2025/07/31
- Product number
- 159441
- Product name
- Diethyl acetylenedicarboxylate
- Purity
- 95%
- Packaging
- 100g
- Price
- $340.2
- Updated
- 2025/07/31
Diethyl acetylenedicarboxylate Chemical Properties,Usage,Production
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
64-17-5
142-45-0
762-21-0
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 Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Diethyl acetylenedicarboxylate manufacturers
- Product
- diethylbut-2-indioat 762-21-0
- Price
- US $3.00-9.00/KG
- Min. Order
- 0.1KG
- Purity
- 99%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2025-06-27
- Product
- Diethyl acetylenedicarboxylate 762-21-0
- Price
- US $1.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 10 mt
- Release date
- 2025-03-14
- Product
- Diethyl acetylenedicarboxylate 762-21-0
- Price
- US $10.00/KG/Tin
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 100
- Release date
- 2019-06-28