5-Chloro-2-thiophenecarboxylic Acid Chemical Properties

Melting point:

154-158 °C(lit.)

Boiling point:

287.0±20.0 °C(Predicted)

Density 

1.466 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

3.32±0.10(Predicted)

form 

Powder

color 

Cream-yellow

BRN 

118361

InChI

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

InChIKey

QZLSBOVWPHXCLT-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

24065-33-6(CAS DataBase Reference)

NIST Chemistry Reference

5-Chloro-2-thiophenecarboxylic acid(24065-33-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36-43-36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

XM8400000

HazardClass 

IRRITANT

HS Code 

29349990

MSDS

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

5-Chloro-2-thiophenecarboxylic Acid Usage And Synthesis

Chemical Properties

White to light yellow crystal powder

Uses

A metabolite of Rivaroxaban (R538000).

Uses

5-Chlorothiophene-2-carboxylic acid can be used in the synthesis of the following:

• rivaroxaban, an oxazolidinone derivative used in the treatment of thromboembolic disorders
• 5-chloro-4-nitrothiophene-2-carboxylic acid, which can be used in the synthesis of thieno[2,3-b][1,4]thiapezine-5-ones

Synthesis

The compound 5-chlorothiophene-2-carboxylic acid is a crucial intermediate in the synthesis of rivaroxaban. Due to its significance, numerous researchers have investigated various methods of synthesizing it. The synthesis of this compound involves the utilization of different starting materials, namely, 2-chlorothiophene, 2-chloro-5-bromothiophene, and 5-chloro-2-acetylthiophene, depending on the specific approach employed.

1. This method takes 2-chlorothiophene as an initial raw material, carrying out Friedel-crafts acylation with trichloroacetyl chloride under the action of aluminum trichloride to generate 2-trichloroacetyl-5-chlorothiophene, and then carrying out liquid alkali hydrolysis to obtain a target product.
2. This method reacts 5-chloro-2-bromothiophene with magnesium to generate a Grignard reagent, introducing carbon dioxide for inserting carbonyl and performing acid-base treatment to obtain a product.
3. 5-chloro-2-acetylthiophene is used as a raw material and is oxidized by sodium chlorite and potassium dihydrogen phosphate system to obtain a target compound.

5-Chloro-2-thiophenecarboxylic Acid(24065-33-6)Related Product Information

• Rivaroxaban Impurity 43
• 2-[(2R)-2-Hydroxy-3-[[4-(3-oxo-4-Morpho linyl)phenyl]aMino]propyl]-1H-isoindole-1 ,3(2H)-dione
• AcetaMide, N-[[(5S)-2-oxo-3-[4-(3-oxo-4-Morpholinyl)phenyl]-5-oxazolidinyl]Methyl]-
• 2-Thiophenecarboxylic acid
• (S)-2-(3-chloro-2-hydroxypropyl)isoindoline-1,3-dione
• 4-(4-AMINOPHENYL)MORPHOLIN-3-ONE
• Urea, N,N'-bis[[(5S)-2-oxo-3-[4-(3-oxo-4-Morpholinyl)phenyl]-5-oxazolidinyl]Methyl]-
• Rivaroxaban Impurity 41
• (S)-2-(2-(5-chloro-N-(4-(5-((5-chlorothiophene-2-carboxamido)methyl)-2-oxooxazolidin-3-yl)phenyl)thiophene-2-carboxamido)ethoxy)acetic acid
• (S)-(+)-Glycidyl Phthalimide
• 4-(4-NITROPHENYL)MORPHOLIN-3-ONE
• Rivaroxaban Impurity 36
• 2-Chloro-5-thiophenecarboxaldehyde
• Rivaroxaban Impurity 34
• Rivaroxaban iMpurity 5
• Rivaroxaban Impurity 38
• Rivaroxaban Impurity 44
• Rivaroxaban Impurity 48