5-CHLOROTHIOPHENE-2-CARBONYL CHLORIDE Chemical Properties

Melting point:

4℃

Boiling point:

122-127℃/16Torr

Density 

1.50

refractive index 

1.6040 to 1.6080

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Oil

color 

Colourless to Pale Yellow

Water Solubility 

Slightly soluble in water.

Sensitive 

Moisture Sensitive

Stability:

Hygroscopic

InChI

InChI=1S/C5H2Cl2OS/c6-4-2-1-3(9-4)5(7)8/h1-2H

InChIKey

BMPDCQVRKDNUAP-UHFFFAOYSA-N

SMILES

C(Cl)(C1SC(Cl)=CC=1)=O

CAS DataBase Reference

42518-98-9(CAS DataBase Reference)

Safety Information

Risk Statements 

36-43

Safety Statements 

26-36

RIDADR 

3265

HazardClass 

IRRITANT

HazardClass 

8

PackingGroup 

Ⅲ

HS Code 

29339900

5-CHLOROTHIOPHENE-2-CARBONYL CHLORIDE Usage And Synthesis

Chemical Properties

Colorless to light yellow liquid

Uses

5-Chlorothiophene-2-carbonyl chloride used as a intermediate for rivaroxaban.

Synthesis

General procedure for the synthesis of 5-chloro-2-thiophene carbonyl chloride from 2-acetyl-5-chlorothiophene: To a mixed solution containing 2-acetyl-5-chlorothiophene (0.161 mg, 1.0 mmol), pyridine (0.012 mL, 0.15 mmol), and chlorobenzene (0.35 mL), at room temperature, disulfur dichloride (S2Cl2, 0.16 mL 2.0 mmol) with continuous stirring. After 2 hours of reaction, sulfuryl chloride (SO2Cl2, 0.121 mL, 1.5 mmol) was added dropwise and stirring was continued for 0.5 hours at room temperature. Subsequently, the reaction mixture was heated to 132 °C and stirred at this temperature for 15 hours. Upon completion of the reaction, the reaction mixture was diluted with deuterated chloroform (CDCl3, 2 mL) and an internal standard (tributyl phosphate, 1BU3PO4, 0.0552 mL, 0.20 mmol) was added for nuclear magnetic resonance (1H NMR) analysis.1H NMR analysis showed an 80% yield of 5-chloro-2-thiophene carbonyl chloride.1H NMR (PhCl. CDCl3, 400 MHz) chemical shift values: δ = 7.99 (d, J = 4 Hz, 1H), 6.86 (d, J = 4 Hz, 1H).

References

[1] Patent: WO2017/5606, 2017, A1. Location in patent: Page/Page column 33
[2] Patent: WO2016/150937, 2016, A1. Location in patent: Page/Page column 27
[3] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 1083,1103
[4] Journal of Organic Chemistry, 2015, vol. 80, # 20, p. 10370 - 10374
[5] Patent: WO2016/202757, 2016, A1. Location in patent: Page/Page column 30

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