| Identification | More | [Name]
Ethyl 2-butynoate | [CAS]
4341-76-8 | [Synonyms]
2-BUTYNOIC ACID ETHYL ESTER
ETHYL 2-BUTYNOATE
ETHYL TETROLATE
TETROLIC ACID ETHYL ESTER
Ethyl 1-propynecarboxylate
Ethyl 3-methylpropiolate
2-Butynoic acid ethyl ester~Ethyl tetrolate
Ethyltetrolate,Tetrolicacidethy
Ethyl2-butynoate,98+%
Ethyl Butynoate | [EINECS(EC#)]
224-395-6 | [Molecular Formula]
C6H8O2 | [MDL Number]
MFCD00015182 | [Molecular Weight]
112.13 | [MOL File]
4341-76-8.mol |
| Questions And Answer | Back Directory | [Synthesis]
Propynic acid (0.51 mmol) and ethanol (0.56 mmol) were dissolved in 1 mL of dichloromethane. This solution was then slowly added dropwise at 0°C to 1 mL of dichloromethane containing N,N'-dicyclohexylcarbodiimide (0.51 mmol) and 4-dimethylaminopyridine (1 mol%). The reaction mixture was stirred at room temperature for 3 hours. After the reaction was complete, the reaction mixture was diluted with water and extracted with ethyl acetate. The separated organic layer was washed with brine (2 mL) and dried over anhydrous magnesium sulfate. The magnesium sulfate solid was removed by filtration. The filtrate was concentrated under vacuum, and the residue was purified by silica gel column chromatography (using a 10:1 mixture of ethyl acetate and n-hexane) to obtain the target product, ethyl 2-butynedoate.  Figure 2. Synthetic Route of Ethyl 2-butynoate |
| Chemical Properties | Back Directory | [Boiling point ]
160-161 °C/730 mmHg (lit.) | [density ]
0.962 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.436(lit.)
| [Fp ]
145 °F
| [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
Chloroform, Ethyl Acetate | [form ]
Powder | [color ]
Grey to red to brown | [Specific Gravity]
0.962 | [Water Solubility ]
Miscible with water, chloroform and ethyl acetate. | [Sensitive ]
Air Sensitive | [BRN ]
1744948 | [InChI]
1S/C6H8O2/c1-3-5-6(7)8-4-2/h4H2,1-2H3 | [InChIKey]
FCJJZKCJURDYNF-UHFFFAOYSA-N | [SMILES]
CCOC(=O)C#CC | [CAS DataBase Reference]
4341-76-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Ethyl 2-butynoate(4341-76-8) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
1993 | [WGK Germany ]
3
| [F ]
10-23 | [Hazard Note ]
Irritant | [HazardClass ]
3.2 | [PackingGroup ]
III | [HS Code ]
29161900 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Ethyl 2-butynoate is gray or reddish brown solid powder at room temperature and pressure, insoluble in water, soluble in ethyl acetate and chloroform. | [Uses]
Ethyl 2-butynoate is used as a precursor for the synthesis of 3-ethyl, 1-methyl 1-(2-nitrophenyl)-cyclopent-3-ene-1,3-dicarboxylate, alkenylsilanols and tricyclic aziridine derivatives. It acts as a methanogenesis inhibitor. As an electron deficient alkyne derivative, it plays a vital role in the preparation of 1,3-dienes catalyzed by rhodium(I)/H8-BINAP complex. | [Synthesis Reference(s)]
Organic Syntheses, Coll. Vol. 7, p. 226, 1990
The Journal of Organic Chemistry, 38, p. 3588, 1973 DOI: 10.1021/jo00960a032 | [General Description]
Ethyl 2-butynoate, a 2-alkynoate is a methanogenesis inhibitor. It is an electron deficient internal alkyne that has been reported to undergo codimerization with alkenes to form 1,3-dienes catalyzed by rhodium(I)/H8-BINAP complex. The annulation of thioamides with ethyl 2-butynoate catalyzed by tri-n-butylphosphine to form thiazolines has been investigated. |
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