| Identification | More | [Name]
4-PENTYNOIC ACID | [CAS]
6089-09-4 | [Synonyms]
4-PENTYNOIC ACID
PROPARGYLACETIC ACID
TIMTEC-BB SBB009121
Pent-4-yn-1-oic acid
pent-4-yn-1-oicacid
4-Pentynoicacid,98%
Pentane-4-ynoic acid | [EINECS(EC#)]
228-028-0 | [Molecular Formula]
C5H6O2 | [MDL Number]
MFCD00004407 | [Molecular Weight]
98.1 | [MOL File]
6089-09-4.mol |
| Chemical Properties | Back Directory | [Appearance]
white to beige crystalline powder or flakes | [Melting point ]
54-57 °C(lit.)
| [Boiling point ]
110 °C30 mm Hg(lit.)
| [density ]
1.1133 (rough estimate) | [refractive index ]
1.3930 (estimate) | [Fp ]
75 °C
| [storage temp. ]
2-8°C
| [form ]
Crystalline Powder or Flakes | [pka]
4.30±0.10(Predicted) | [color ]
White to beige | [Water Solubility ]
Soluble in low polarity organic solvents. Soluble in water. | [Sensitive ]
Light & Air Sensitive & Hygroscopic | [BRN ]
1742047 | [InChIKey]
MLBYLEUJXUBIJJ-UHFFFAOYSA-N | [LogP]
0.402 (est) | [CAS DataBase Reference]
6089-09-4(CAS DataBase Reference) | [Storage Precautions]
Air sensitive;Store under nitrogen;Light sensitive |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
3
| [RTECS ]
SC4751000
| [F ]
8-10-23 | [Hazard Note ]
Corrosive | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29161900 |
| Hazard Information | Back Directory | [Chemical Properties]
white to beige crystalline powder or flakes | [Uses]
4-Pentynoic Acid is a hypoglycemic agent shown to increase liver tyrosine aminotransferase and plasma corticosterone while decreasing blood sugar in rats. | [General Description]
4-Pentynoic acid undergoes copper-catalyzed intramolecular cyclizations to form enol lactones. It also reacts with 1-bromo-1-alkynes in the presence of a Pd catalyst to yield biologically active ynenol lactones. | [Synthesis]
General procedure for the synthesis of 4-pentynoic acid from 4-pentyn-1-ol: 4-pentyn-1-ol (1 mL, 10.7 mmol) was dissolved in acetone and the solution was cooled to 0 °C. Jones' reagent was slowly added dropwise under vigorous stirring until the reaction mixture remained orange in color. Subsequently, the reaction mixture was allowed to warm up to room temperature and Jones reagent was continued to be added dropwise to maintain the orange color. The reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, water was added and extracted several times with ether (Et2O). The organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate (Na2SO4). The solvent was removed by concentration under reduced pressure to give the crude product. Purification by rapid chromatography on silica gel (eluent: hexane/ether=8:2) gave the colorless oily product 4-pentynoic acid in 82% yield.1H NMR (400MHz, CDCl3) δ: 2.61-2.59 (m, 2H), 2.52-2.48 (m, 2H), 1.98-1.95 (m, 1H) ppm. | [References]
[1] Organic Letters, 2016, vol. 18, # 11, p. 2600 - 2603
[2] Patent: WO2016/128541, 2016, A1. Location in patent: Page/Page column 53
[3] Patent: WO2017/162834, 2017, A1. Location in patent: Page/Page column 45
[4] Tetrahedron, 2009, vol. 65, # 24, p. 4664 - 4670
[5] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 2976 - 2979 |
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