| Identification | More | [Name]
4-(2-THIENYL)BUTYRIC ACID | [CAS]
4653-11-6 | [Synonyms]
2-THIOPHENEBUTYRIC ACID
4-(2-THIENYL)BUTYRIC ACID
2-Thiophenebutanoic acid
4-(2-Thienyl)butanoic acid
gamma-(alpha-Thienyl)butyric acid
4-(2-Thienyl)butyricacid,98+%
2-(2-THIENYL)BUTYRIC ACID
4-(2-Thienyl)butyric acid, GC 97%
Thiophene-2-butanoic acid | [EINECS(EC#)]
225-090-0 | [Molecular Formula]
C8H10O2S | [MDL Number]
MFCD00005463 | [Molecular Weight]
170.23 | [MOL File]
4653-11-6.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR SLIGHTLY BROWNISH LIQUID | [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.)
| [Fp ]
>230 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Liquid | [pka]
4.71±0.10(Predicted) | [color ]
Clear slightly brown | [Specific Gravity]
1.1690 | [BRN ]
127982 | [CAS DataBase Reference]
4653-11-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29309099 |
| Hazard Information | Back Directory | [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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