4-(2-THIENYL)BUTYRIC ACID Chemical Properties

Melting point:

13.5-15 °C

Boiling point:

122°C 0,3mm

Density 

1.169 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.532(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

4.71±0.10(Predicted)

form 

Liquid

Specific Gravity

1.1690

color 

Clear slightly brown

BRN 

127982

CAS DataBase Reference

4653-11-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29309099

MSDS

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• Language:English Provider:ACROS
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4-(2-THIENYL)BUTYRIC ACID Usage And Synthesis

Chemical Properties

CLEAR SLIGHTLY BROWNISH LIQUID

Uses

2-Thiophenebutanoic Acid is used to prepare cell-penetrating peptide α-keto-amide calpain inhibitors as potential treatment for muscular dystrophy. it is also used to prepare isochroman carboxylic acid derivatives as potential anti-diabetic agents.

Definition

ChEBI: A monocarboxylic acid that is butyric acid bearing a 2-thienyl group at position 4.

Synthesis

The general procedure for the synthesis of 4-(2-thienyl)butyric acid from 3-(2-thiophenecarbonyl)propionic acid was as follows: 4-oxo-4-(thiophen-2-yl)butyric acid (2.3 g, 12.48 mmol) was dissolved in ethylene glycol (30 mL), and hydrazine hydrate (99%, 2.2 mL, 45.9 mmol) and potassium hydroxide pellets (2.37 g, 42.4 mmol). The reaction mixture was heated to 180 °C and maintained for 10 hours. After completion of the reaction, it was cooled to room temperature and the reaction mixture was diluted with water. The aqueous layer was washed with ether, acidified with 6N hydrochloric acid and extracted with ether. The organic layers were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 2% dichloromethane solution in methanol) to give 4-(thiophen-2-yl)butanoic acid (1.8 g, 85% yield). The product was confirmed by 1H NMR (300 MHz, DMSO-d6) and mass spectrometry (ESI): 1H NMR δ 12.06 (s, 1H), 7.31-7.29 (m, 1H), 6.94-6.91 (m, 1H), 6.84-6.82 (m, 1H), 2.82-2.77 (t, J=7.7 Hz, 2H), 2.27- 2.22 (t, J=7.3Hz, 2H), 1.86-1.76 (m, 2H); MS (ESI) m/z: [M+H]+ Calculated value 170.04, measured value 170.8.

References

[1] European Journal of Medicinal Chemistry, 1998, vol. 33, # 11, p. 867 - 877
[2] Patent: WO2011/88187, 2011, A1. Location in patent: Page/Page column 60-61
[3] Patent: WO2010/76188, 2010, A1. Location in patent: Page/Page column 17-19
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1185 - 1193
[5] Archiv der Pharmazie, 1988, vol. 321, # 10, p. 735 - 738

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