TERT-BUTYL PROPIOLATE Chemical Properties

Melting point:

18-20 °C (lit.)

Boiling point:

52-53 °C/27 mmHg (lit.)

Density 

0.919 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.418(lit.)

Flash point:

82 °F

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

form 

Liquid

color 

Clear colorless to yellow

Sensitive 

Air Sensitive

BRN 

1747175

InChI

InChI=1S/C7H10O2/c1-5-6(8)9-7(2,3)4/h1H,2-4H3

InChIKey

XGTPDIIFEPTULX-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)C#C

CAS DataBase Reference

13831-03-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-36/37/38

Safety Statements 

26-36/37/39

RIDADR 

UN 3272 3/PG 3

WGK Germany 

3

F 

4.5-10-23

HazardClass 

3.1

PackingGroup 

II

HS Code 

29161995

MSDS

• Language:English Provider:SigmaAldrich

TERT-BUTYL PROPIOLATE Usage And Synthesis

Uses

tert-Butyl propiolate may be used in the preparation of heterocycles, alkaloids, and unsaturated amino acids.

Uses

TERT-BUTYL PROPIOLATE is used to prepare heterocycles,1,2 alkaloids,3 and unsaturated amino acids.4

General Description

tert-Butyl propiolate is an ester. It reacts with methimazole to afford tert-butyl (E)-3-(1-methyl-1H-imidazol-2-ylthio) acrylate. Crystallographic data for the lithium enolate of tert-butyl propiolate has been described..

Synthesis

General procedure for the synthesis of tert-butyl propargylate from propargyl acid and tert-butanol: About 60 g of propargyl acid, about 100 g of N,N'-dicyclohexylcarbodiimide, about 10 g of 4-(dimethylamino)pyridine, and about 20 g of tert-butanol were dissolved in tetrahydrofuran, and the reaction was stirred for about 24 hours. Upon completion of the reaction, extraction was carried out with dichloromethane and water. The extracted organic layer was dried with a chemical desiccant and subsequently purified by column chromatography to give about 80 g of tert-butyl propargylate.

References

[1] Patent: JP2016/533394, 2016, A. Location in patent: Paragraph 0103
[2] Organic Letters, 2018, vol. 20, # 13, p. 4023 - 4027

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