5-Phenylthiophene-2-carboxylic acid

5-Phenylthiophene-2-carboxylic acid Property

Melting point:

186-190°C

Boiling point:

393.6±30.0 °C(Predicted)

Density 

1.303±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

form 

powder to crystal

pka

3.52±0.10(Predicted)

color 

White to Orange to Green

λmax

310nm(EtOH)(lit.)

CAS DataBase Reference

19163-24-7(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-37/39

HazardClass 

IRRITANT

HS Code 

2934999090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

5-Phenylthiophene-2-carboxylic acid Chemical Properties,Usage,Production

Uses

Thiophene derivatives are widely used in the synthesis of pesticides, pharmaceuticals, chemical reagents, dyes, and polymer auxiliaries. 5-Phenylen-2-carboxylic acid has extensive applications in organic synthesis.

Definition

ChEBI: 5-Phenylthiophene-2-carboxylic acid is a thiophenecarboxylic acid.

Synthesis

GENERAL STEPS: To a mixed solution of methanol (5 mL) and tetrahydrofuran (5 mL) of 2-methoxycarbonyl-5-phenylthiophene (437 mg) was added 1 N aqueous sodium hydroxide (3 mL), and the reaction was stirred for 2 hours at room temperature. After completion of the reaction, 1 N hydrochloric acid (5 mL) was slowly added to the reaction mixture for acidification. The precipitated solid was collected by filtration and washed with a small amount of cold water and dried under vacuum to give 5-phenylthiophene-2-carboxylic acid (397 mg, 97.1% yield). The product was confirmed by NMR hydrogen spectrum (DMSO-d6, δ): 7.3-7.5 (3H, m), 7.58 (1H, d, J = 3.9 Hz), 7.6-7.8 (3H, m), 13.15 (1H, wide s). Electrospray mass spectrometry (ESI-MS) showed m/z: 203 ([M-H]-).

References

[1] Patent: US6770667, 2004, B1. Location in patent: Page column 11
[2] ChemMedChem, 2011, vol. 6, # 2, p. 362 - 377
[3] European Journal of Medicinal Chemistry, 2017, vol. 137, p. 96 - 107
[4] Journal of Medicinal Chemistry, 2010, vol. 53, # 15, p. 5536 - 5548