4-Pentynoic acid

Base Information

• Chemical Name: 4-Pentynoic acid
• CAS No.: 6089-09-4
• Molecular Formula: C5H6O2
• Molecular Weight: 98.1014
• Hs Code.: 29161900
• European Community (EC) Number: 228-028-0
• DSSTox Substance ID: DTXSID20209730
• Nikkaji Number: J69.139I
• Wikidata: Q27455468
• Mol file: 6089-09-4.mol

Synonyms:4-pentynoic acid

Chemical Property of 4-Pentynoic acid

Chemical Property:

• Appearance/Colour: white to beige crystalline powder or flakes
• Vapor Pressure: 0.146mmHg at 25°C
• Melting Point: 54-57 °C(lit.)
• Refractive Index: 1.3930 (estimate)
• Boiling Point: 199.2 °C at 760 mmHg
• PKA: 4.30±0.10(Predicted)
• Flash Point: 90.8 °C
• PSA: 37.30000
• Density: 1.096g/cm³
• LogP: 0.48440
• Storage Temp.: 2-8°C
• Sensitive.: Light & Air Sensitive & Hygrosco
• Water Solubility.: Soluble in low polarity organic solvents. Soluble in water.
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 98.036779430
• Heavy Atom Count: 7
• Complexity: 107

Purity/Quality:

97% ^*data from raw suppliers

4-Pentynoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C#CCCC(=O)O
• General Description: 4-Pentynoic acid, also known as propargylacetic acid, is an acetylenic carboxylic acid that serves as a key reactant in organic synthesis, particularly in click chemistry and gold-catalyzed cyclization reactions. It is used in the formation of carotenoid-monosaccharide conjugates via azide-alkyne click reactions, where it acts as a linker to produce amphipathic derivatives with potential biological applications. Additionally, it undergoes gold-catalyzed cyclization to form γ- or δ-alkylidene lactones, demonstrating its versatility in stereoselective transformations. The compound's reactivity and functional group compatibility make it valuable in synthetic chemistry for constructing complex molecular architectures.

Technology Process of 4-Pentynoic acid

There total 25 articles about 4-Pentynoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

pent-1-yn-5-ol (5390-04-5) → 4-pentynoic acid (6089-09-4)

Guidance literature:

With Jones reagent; In acetone; at 20 ℃; for 1h;

DOI:10.1021/acs.orglett.6b00983

Reference yield: 91.0%

4-pentyn-1-al (18498-59-4) → 4-pentynoic acid (6089-09-4)

Guidance literature:

With 4H₃N*4H⁽¹⁺⁾*CuMo₆O₁₈(OH)6^(4-); water; oxygen; sodium carbonate; at 50 ℃; for 12h; under 760.051 Torr;

DOI:10.1002/cctc.201701599

Reference yield: 84.0%

5-trimethylsilyl-pent-5-yn-1-oic acid (128545-15-3) → 4-pentynoic acid (6089-09-4)

Guidance literature:

5-trimethylsilyl-pent-5-yn-1-oic acid; With sodium hydroxide; water; In toluene; at 20 ℃; for 0.333333h;

With sulfuric acid; In water; toluene; at 20 - 40 ℃; for 0.166667h;

upstream raw materials:

prop-2-yn-1-ylpropanedioic acid

pent-1-yn-5-ol

4,5-dibromopentanoic acid

diethyl propargylmalonate

Downstream raw materials:

methyl pent-4-ynoate

7-cyclohex-1-enyl-hepta-4,6-diynoic acid

5-methyl-2-furanone

(E)-2,4-pentadienoic acid

Refernces

Synthesis of carotenoid-monosaccharide conjugates via azide–alkyne click-reaction

10.1016/j.tet.2016.12.035

The research focuses on the synthesis of carotenoid-monosaccharide conjugates through an azide-alkyne click reaction using bis-triphenylphosphano-copper(I)-butyrate (C3H7COOCu(PPh3)2) as a catalyst. The study involves coupling carotenoid pentynoates with protected and unprotected sugar azides to form amphipathic carotenoid-sugar derivatives. The reactants include hydroxy carotenoids, 4-pentynoic acid, various sugar azides, and the copper catalyst. The synthesized compounds were characterized using various analytical techniques such as NMR spectroscopy, mass spectrometry (MALDI-TOF), infrared spectroscopy, and elemental analysis. The experiments resulted in the formation of target triazoles with good to excellent yields, offering a new approach for synthesizing biologically interesting molecules with potential applications in enhancing the stability of cell membranes and acting as antioxidants.

A mild access to γ- or δ-alkylidene lactones through gold catalysis

10.1016/j.tetlet.2006.06.129

The research explores an efficient and stereoselective method for converting x-acetylenic acids into enol lactones using gold catalysis. The study investigates the cyclization of acetylenic acids mediated by gold species, focusing on finding the optimal conditions for this transformation. Key chemicals involved in the research include gold chloride (AuCl), potassium carbonate (K2CO3), and various acetylenic acids such as 4-pentynoic acid, 5-hexynoic acid, and 6-heptynoic acid. The researchers discovered that the combination of AuCl and K2CO3 in solvents like acetonitrile or tetrahydrofuran (THF) effectively promoted the cyclization, yielding the desired enol lactones with high selectivity for the exo-dig product. The study also examines the influence of different substituents on the acetylenic acids and their impact on the reaction outcomes, highlighting the role of these chemicals in achieving the desired products with specific stereochemistry.