5-Nitrothiophene-2-carboxylic acid Chemical Properties

Melting point:

154-159℃

Boiling point:

367.2±27.0 °C(Predicted)

Density 

1.676±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

2.69±0.10(Predicted)

form 

Solid

color 

Pale yellow

InChIKey

UNEPVPOHGXLUIR-UHFFFAOYSA-N

CAS DataBase Reference

6317-37-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich

5-Nitrothiophene-2-carboxylic acid Usage And Synthesis

Chemical Properties

Solid

Uses

5-Nitrothiophene-2-carboxylic Acid is a reagent used in the preparation of benzothiophene amides which fuctions as nicotinamide ribosyltransferase inhibitors with potential antitumor and anticancer activities. It also functions as an intermediate in varying organic transformations.

Synthesis Reference(s)

Canadian Journal of Chemistry, 44, p. 2881, 1966 DOI: 10.1139/v66-428
Journal of Medicinal Chemistry, 34, p. 2112, 1991

Synthesis

General procedure for the synthesis of 5-nitrothiophene-2-carboxylic acid from 5-nitrothiophene-2-carboxaldehyde: 5-nitrothiophene-2-carboxaldehyde (1.685 g, 10.72 mmol) was dissolved in dioxane (30 mL) with sulfamic acid (1.249 g, 12.87 mmol) and cooled down to 0 °C. Subsequently, an aqueous solution of sodium chlorite (1.940 g, 21.44 mmol) was added slowly and dropwise (14 mL). The reaction mixture was gradually warmed to room temperature and stirred continuously for 2 hours. A second batch of 5-nitrothiophene-2-carbaldehyde (1.966 g, 12.51 mmol) was treated at the same molar ratio under the same conditions. The two reaction mixtures were combined and extracted by partitioning with ethyl acetate and water. The organic phase was extracted twice with 5% NaHCO3 solution and discarded. The basic aqueous phase was adjusted to pH=2 with 2N HCl and extracted twice with ethyl acetate. The organic layers were combined, washed with brine and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give 5-nitrothiophene-2-carboxylic acid (Int.53) (3.6 g, 20.79 mmol, MS/ESI+ 173.9 [MH]+).

References

[1] Patent: US4220793, 1980, A
[2] Patent: US4220793, 1980, A
[3] Patent: US4220793, 1980, A
[4] Patent: WO2004/18480, 2004, A1. Location in patent: Page 155
[5] Helvetica Chimica Acta, 2002, vol. 85, # 12, p. 4485 - 4517

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