2-Thiophenecarbonyl chloride Chemical Properties

Boiling point:

206-208 °C (lit.)

Density 

1.371 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.590(lit.)

Flash point:

195 °F

storage temp. 

2-8°C

solubility 

Chloroform

form 

Liquid

Specific Gravity

1.371

color 

Clear colorless to yellow-gray

Sensitive 

Moisture Sensitive

BRN 

110145

InChIKey

QIQITDHWZYEEPA-UHFFFAOYSA-N

CAS DataBase Reference

5271-67-0(CAS DataBase Reference)

NIST Chemistry Reference

2-Thiophenecarbonyl chloride(5271-67-0)

EPA Substance Registry System

2-Thiophenecarbonyl chloride (5271-67-0)

Safety Information

Hazard Codes 

C

Risk Statements 

34-37

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

F 

8

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29349990

MSDS

• Language:English Provider:Thiophene-2-carbonyl chloride
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Thiophenecarbonyl chloride Usage And Synthesis

Chemical Properties

CLEAR COLOURLESS TO YELLOW-GREY LIQUID

Uses

2-Thiophenecarbonyl chloride was used in the synthesis of building blocks derived from ornithine by undergoing acylation/sulphonation of copper complex of orthinine.

Uses

2-Thiophenecarbonyl Chloride is used in the synthesis of substituted pyridines as selective and highly effective GPR119 agonists. It is also seen in the preparation of diuretics.

General Description

The postfunctionalization reaction of 2-thiophenecarbonyl chloride with single walled carbon nanotubes (SWCNTs) was studied.

Synthesis

The general procedure for the synthesis of 2-thiophenecarbonyl chloride from 2-acetylthiophene was as follows: to a mixed solution containing 2-acetylthiophene (0.108 mL, 1.0 mmol), pyridine (0.016 mL, 0.20 mmol), and chlorobenzene (0.35 mL), disulfur dichloride (S2Cl2, 0.16 mL, 2.0 mmol) was slowly added at room temperature (S2Cl2, 0.16 mL, 2.0 mmol), while stirring continuously. After the reaction mixture was stirred for 1 hour and 45 minutes, sulfuryl chloride (SO2Cl2, 0.162 mL, 2.0 mmol) was added dropwise, followed by continued stirring for 0.5 hours at room temperature. Next, the reaction mixture was heated to 132 °C and stirred at this temperature for 14 hours. Upon completion of the reaction, the reaction mixture was diluted with deuterated chloroform (CDCl3, 2 mL) and the internal standard (tributyl phosphate, 1BU3PO4, 0.0552 mL, 0.20 mmol) was added for nuclear magnetic resonance (1H NMR) analysis. The analytical results showed that the yield of 2-thiophenecarbonyl chloride was 90%.

References

[1] Patent: WO2017/5606, 2017, A1. Location in patent: Page/Page column 31-32
[2] Journal of Organic Chemistry, 2015, vol. 80, # 20, p. 10370 - 10374
[3] Patent: WO2016/150937, 2016, A1. Location in patent: Page/Page column 27
[4] Patent: WO2016/202757, 2016, A1. Location in patent: Page/Page column 30; 31
[5] Patent: TW2017/36360, 2017, A

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