2-Ethynylthiophene Chemical Properties

Boiling point:

70℃/20Torr

Density 

1.080

refractive index 

n20/D1.580

Flash point:

42℃

storage temp. 

Keep in dark place,Sealed in dry,Store in freezer, under -20°C

form 

clear liquid

color 

Light yellow to Brown

InChI

InChI=1S/C6H4S/c1-2-6-4-3-5-7-6/h1,3-5H

InChIKey

LWISLHRIEATKTM-UHFFFAOYSA-N

SMILES

C1(C#C)SC=CC=1

CAS DataBase Reference

4298-52-6

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-36/37/38-36

Safety Statements 

16-23-26-36/37/39

RIDADR 

UN 1993C 3 / PGIII

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

3

PackingGroup 

III

HS Code 

29349990

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Eye Irrit. 2

2-Ethynylthiophene Usage And Synthesis

Chemical Properties

Clear yellow liquid

Uses

2-Ethynylthiophene is used in preparation of triazole derivative as Hsp90 inhibitors and anti-cancer metastasis drugs.

Definition

ChEBI: 2-Ethynylthiophene is a heteroarene.

Synthesis Reference(s)

The Journal of Organic Chemistry, 41, p. 1487, 1976 DOI: 10.1021/jo00871a001
Synthesis, p. 589, 1996 DOI: 10.1055/s-1996-4265

Synthesis

The general procedure for the synthesis of 2-trimethylsilylthienylthiophene from 2-trimethylsilylthienylthiophene was as follows: 2-[(trimethylmethylsilyl)ethynyl]thiophene (1 mmol), an inorganic base (potassium tert-butoxide, sodium tert-butoxide, potassium hydroxide, sodium hydroxide, or potassium trimethylsilyl, sodium trimethylsilyl, 0.05 mmol), and 2 mL of DMA or DMSO solvent were added in turn to a 10-mL in a sealed tube. The reaction mixture was placed in an oil bath at 60 °C and stirred for 6 h, during which the reaction progress was monitored by TLC. Upon completion of the reaction, an equal volume of homotrimethylene or n-undecane was added to the crude product. The exact yield of the product was determined by GC and GC-MS. The yields of the products were 59%, 66%, 75%, 77%, 92%, and 85% when DMSO was used as the reaction solvent and potassium tert-butanol, sodium tert-butanol, potassium hydroxide, sodium hydroxide, or potassium trimethylmethylsilyl, sodium trimethylmethylsilyl were used as the catalysts, respectively. When DMA was used as the reaction solvent, with the same catalyst, the yields of the products were 51%, 60%, 67%, 70%, 81%, 72%, respectively.

References

[1] Journal of Organic Chemistry, 1996, vol. 61, # 20, p. 6906 - 6921
[2] Patent: CN107459438, 2017, A. Location in patent: Paragraph 0080; 0081
[3] Organic Letters, 2017, vol. 19, # 19, p. 5182 - 5185
[4] Chemistry - A European Journal, 2018, vol. 24, # 15, p. 3725 - 3728
[5] Journal of Chemical Research, 2007, # 12, p. 728 - 732

2-Ethynylthiophene(4298-52-6)Related Product Information

• Cephalothin sodium
• Trimethylsilylacetylene
• Thiophene
• Tetrahydrothiophene
• Thifensulfuron
• Acetylene
• ETHYNYLMAGNESIUM BROMIDE
• 1-BUTEN-3-YNE
• Dibenzothiophene
• 3-ETHYNYLTHIOPHENE 96
• 1-[5-(2-PHENYLETH-1-YNYL)-2-THIENYL]ETHAN-1-ONE
• ATRELEUTON
• 1-{5-[3-(DIMETHYLAMINO)PROP-1-YNYL]-2-THIENYL}ETHAN-1-ONE
• 5-(2-PHENYLETH-1-YNYL)THIOPHENE-2-CARBALDEHYDE
• 2-[(4-BROMOPHENYL)ETHYNYL] THIOPHENE
• 1-[5-(3-HYDROXYPROP-1-YNYL)-2-THIENYL]ETHAN-1-ONE
• 1-[5-(3-HYDROXY-3-METHYLBUT-1-YNYL)-2-THIENYL]ETHAN-1-ONE
• 2-Ethynylthiophene