3-Chlorothiophene-2-carboxylic acid Chemical Properties

Melting point:

186-190 °C (lit.)

Boiling point:

291.7±20.0 °C(Predicted)

Density 

1.466 (estimate)

storage temp. 

2-8°C

solubility 

DMSO (Sparingly), Methanol (Slightly)

pka

3.09±0.10(Predicted)

form 

solid

color 

White to Off-White

BRN 

121052

InChI

InChI=1S/C5H3ClO2S/c6-3-1-2-9-4(3)5(7)8/h1-2H,(H,7,8)

InChIKey

BXEAAHIHFFIMIE-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

59337-89-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29349990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Chlorothiophene-2-carboxylic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

3-Chlorothiophene-2-carboxylic acid may be used in the synthesis of 3-chloro-N-[(4-chlorophenyl)(methyl)carbamothioyl]thiophene-2-carboxamide.

Synthesis

GENERAL STEPS: Methyl 3-chlorothiophene-2-carboxylate (50 g, 0.28 mol) was dissolved in methanol (100 mL), aqueous sodium hydroxide solution (2M, 400 mL) was added slowly, and the reaction temperature was maintained at 0 °C. The reaction mixture was stirred at room temperature for 2 hours. After removal of methanol by distillation under reduced pressure, the aqueous phase was washed with ether and subsequently acidified with 2N hydrochloric acid to pH < 3. The precipitated white solid was collected by filtration and dried under vacuum to give 3-chlorothiophene-2-carboxylic acid (45 g, 98% yield). Mass spectrometry (MS) analysis showed a molecular ion peak (M+H+) of 163.

References

[1] Heterocycles, 1985, vol. 23, # 6, p. 1431 - 1435
[2] Patent: WO2012/139425, 2012, A1. Location in patent: Page/Page column 119
[3] Heterocycles, 2007, vol. 71, # 1, p. 87 - 104
[4] Patent: WO2013/28670, 2013, A1. Location in patent: Page/Page column 96
[5] Patent: US9181236, 2015, B2. Location in patent: Page/Page column 107

3-Chlorothiophene-2-carboxylic acid(59337-89-2)Related Product Information

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• Ascoric Acid
• METHYL 3-CHLOROBENZO[B]THIOPHENE-2-CARBOXYLATE
• 3-CHLOROBENZO[B]THIOPHENE-2-CARBOXYLIC ACID
• 3-CHLOROTHIOPHENE-2-CARBOXYLIC ACID METHYL ESTER
• 3-CHLORO-4-(METHYLSULFONYL)THIOPHENE-2-CARBOXYLIC ACID
• 3,4,5-TRICHLOROTHIOPHENE-2-CARBOXYLIC ACID
• METHYL 2,5-DICHLOROTHIOPHENE-3-CARBOXYLATE
• 5-Chloro-2-thiophenecarboxylic Acid
• 5-Chlorothiophene-2-carboxylic acid ethyl ester
• 4-AMINO-5-CHLOROTHIOPHENE-2-CARBOXYLIC ACID METHYL ESTER
• 2,5-DICHLOROTHIOPHENE-3-CARBOXYLIC ACID