4-PENTYNOIC ACID Chemical Properties

Melting point:

54-57 °C(lit.)

Boiling point:

110 °C30 mm Hg(lit.)

Density 

1.1133 (rough estimate)

refractive index 

1.3930 (estimate)

Flash point:

75 °C

storage temp. 

2-8°C

pka

4.30±0.10(Predicted)

form 

Crystalline Powder or Flakes

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)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45

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

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-PENTYNOIC ACID Usage And Synthesis

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.

Uses

4-Pentynoic acid was used:

• as building block for the synthesis of library of eight sequence-defined model oligomers
• in one-pot synthesis of the complex polycyclic heterocycles benzo[4,5]imidazo[1,2-c]pyrrolo[1,2-a]quinazolinone derivatives
• in the synthesis of various allenenols lactones [5(E)-(2-allenylidene)-tetrahydro-2-furanones]
• in the synthesis of a cyctotoxic macrolide by ring-closing metathesis of a bis acetylene

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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