2,5-Dichlorothiophene Chemical Properties

Melting point:

-41--40°C

Boiling point:

162 °C (lit.)

Density 

1.442 g/mL at 25 °C (lit.)

refractive index 

1.561-1.563

Flash point:

59 °C

storage temp. 

2-8°C

form 

liquid

Specific Gravity

1.442

color 

Colorless to Light yellow to Light orange

BRN 

109887

InChI

InChI=1S/C4H2Cl2S/c5-3-1-2-4(6)7-3/h1-2H

InChIKey

FGYBDASKYMSNCX-UHFFFAOYSA-N

SMILES

C1(Cl)SC(Cl)=CC=1

CAS DataBase Reference

3172-52-9(CAS DataBase Reference)

NIST Chemistry Reference

Thiophene, 2,5-dichloro-(3172-52-9)

EPA Substance Registry System

Thiophene, 2,5-dichloro- (3172-52-9)

Safety Information

Hazard Codes 

T+,Xn

Risk Statements 

40-26/27/28-36/37/38-20/21/22

Safety Statements 

45-36/37-28A-36-26

RIDADR 

2929

WGK Germany 

3

TSCA 

T

HazardClass 

6.1

PackingGroup 

II

HS Code 

29349990

MSDS

• Language:English Provider:2,5-Dichlorothiophene
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,5-Dichlorothiophene Usage And Synthesis

Chemical Properties

clear colorless to slightly yellow liquid

Uses

2,5-Dichlorothiophene is mainly used as a pharmaceutical intermediate. It is used in the synthesis of 3,4-disubstituted thiophenes.

Synthesis Reference(s)

Tetrahedron, 52, p. 8863, 1996 DOI: 10.1016/0040-4020(96)00433-4

Synthesis

The general procedure for the preparation of 2,5-dichlorothiophene is as follows: 1. 300 g of carbon tetrachloride and 84 g of thiophene were added to a 1000 mL three-necked flask, heated to reflux temperature and then 270 g of N-chlorotoluene diimide was slowly added. 2. After completion of the reaction, the reaction mixture was cooled to room temperature and filtered to remove insoluble impurities. 3. The filtrate was concentrated to recover carbon tetrachloride to give the remaining reaction mixture. 4. 4. the remaining reaction mixture was heated to 100 °C and subjected to reduced pressure distillation. 5. The 100 °C fraction was collected as the target product 2,5-dichlorothiophene in a yield of 145 g, 95% yield and 98.5% purity.

References

[1] Patent: CN105481827, 2016, A. Location in patent: Paragraph 0021; 0022
[2] Journal of Organic Chemistry, 1993, vol. 58, # 11, p. 3072 - 3075
[3] Tetrahedron, 1996, vol. 52, # 26, p. 8863 - 8866
[4] Journal of Chemical Crystallography, 2007, vol. 37, # 6, p. 387 - 398
[5] Patent: US2492644, 1947,

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