232211 Aldrich

4-Pentynoic acid


Synonym: Propargylacetic acid



Related Categories Building Blocks, C1 to C5, Carbonyl Compounds, Carboxylic Acids, Chemical Synthesis,
assay   95%
bp   110 °C/30 mmHg(lit.)
mp   54-57 °C(lit.)
storage temp.   2-8°C



1, 5 g in glass bottle


4-Pentynoic acid was used:
• as building block for the synthesis of library of eight sequence-defined model oligomers1
• in one-pot synthesis of the complex polycyclic heterocycles benzo[4,5]imidazo[1,2-c]pyrrolo[1,2-a]quinazolinone derivatives2
• in the synthesis of various allenenols lactones [5(E)-(2-allenylidene)-tetrahydro-2-furanones]3
• in the synthesis of a cyctotoxic macrolide by ring-closing metathesis of a bis acetylene4

General description

4-Pentynoic acid undergoes copper-catalyzed intramolecular cyclizations to form enol lactones5. It also reacts with 1-bromo-1-alkynes in the presence of a Pd catalyst to yield biologically active ynenol lactones6.

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4-Pentenoic acid

≥98%, stabilized, FG

Safety & Documentation

Safety Information

GHS05  GHS05
Signal word 
Hazard statements 
Precautionary statements 
UN 3261 8 / PGII
WGK Germany 
Protocols & Articles


Introduction of Terminal Azide and Alkyne Functionalities in Polymers

“Click” chemistry, and the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) in particular, is a powerful new synthetic tool in polymer chemistry and material science. Success of the CuAAC in th...
Dr. Joost A. Opsteen
Material Matters 2008, 3.3, 66.
Keywords: Building blocks, Catalysis, Cycloadditions, Esterifications, Materials Science, Nucleophilic substitutions, Polymer science, Polymerization reactions, Radical polymerization, Substitutions, transformation

Related Content

Alkynes and Acetylenic Building Blocks

Aldrich Chemistry lists over 600 alkyne building blocks, including a wide array of propargyl alcohols, acetylenic boron reagents, and halogenated substrates for cross-coupling. Additionally, many of ...
Keywords: Building blocks, Coupling reactions, Cross couplings

Peer-Reviewed Papers


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1. Synthesis of molecularly encoded oligomers using a chemoselective "AB + CD" iterative approach. Trinh TT, Oswald L, Chan-Seng D, et al. Macromol. Rapid Commun. 35(2), 141-5, (2014)


2. Au(I)/Ag(I)-catalyzed cascade approach for the synthesis of benzo[4,5]imidazo[1,2-c]pyrrolo[1,2-a]quinazolinones. Ji X, Zhou Y, Wang J, et al. J. Org. Chem. 78(9), 4312-8, (2013)


3. Palladium-catalyzed synthesis of new unsaturated exo-enol lactones with potential biological activity. Bouyssi D, et al. Tetrahedron Lett. 34(19), 3129-30, (1993)

4. Synthesis of the core structure of cruentaren A. Org. Lett. 9, 655, (2007)


5. Cu(I)-catalyzed intramolecular cyclization of alkynoic acids in aqueous media: a "click side reaction". Mindt TL and Schibli R J. Org. Chem. 72(26), 10247-50, (2007)


6. Tetrahedron Lett. 33, 2811, (1992)

Surface functionalization of exosomes using click chemistry. Smyth T, Petrova K, Payton NM, et al. Bioconjug. Chem. 25(10), 1777-84, (2014)


In situ nanofabrication of hybrid PEG-dendritic-inorganic nanoparticles and preliminary evaluation of their biocompatibility. Sousa-Herves A, Sánchez Espinel C, Fahmi A, et al. Nanoscale 7(9), 3933-40, (2015)


Parahydrogen-induced polarization of carboxylic acids: a pilot study of valproic acid and related structures. Lego D, Plaumann M, Trantzschel T, et al. NMR Biomed. 27(7), 810-6, (2014)


5-[4-(3,3-Dimethylbutoxycarbonyl)phenyl]-4-pentynoic acid and its derivatives inhibit ionotropic gamma-aminobutyric acid receptors by binding to the 4'-ethynyl-4-n-propylbicycloorthobenzoate site. Hamano H, Nagata K, Fukada TN, et al. Bioorg. Med. Chem. 8(3), 665-74, (2000)


Preparation of peptide and other biomolecular conjugates through chemoselective ligations. Galibert M, Renaudet O, Boturyn D, et al. Methods Mol. Biol. 751, 67-79, (2011)


Beil. 2,IV,1693

Aldrich MSDS 1, 1443:C / Corp MSDS 1 (2), 2724:B / FT-IR 1 (2), 943:C / FT-IR 2 (3), 4038:C / FT-NMR 1 (3), 525:C / NMR-Reference 2 (2), 959:D / RegBook 1 (2), 2707:L / Structure Index 1, 426:D:9 / Vapor Phase 3, 1595:C

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