EMAIL THIS PAGE TO A FRIEND

232211 Aldrich

4-Pentynoic acid

95%

Synonym: Propargylacetic acid

Purchase

Properties

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

Description

Packaging

1, 5 g in glass bottle

Application

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.

Price and Availability

Suggested Laboratory Gloves


Laboratory GlovesThis substance has been tested against several types of hand protection for CE compliance. Click below to find the recommended gloves for handling this product.




Search for Answers, Not Just Materials

Customers Also Viewed

4-Pentenoic acid

≥98%, FG

4-Pentynoic acid

purum, ≥97% (GC)

Safety & Documentation

Safety Information

Symbol 
GHS05  GHS05
Signal word 
Danger
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
C
Risk Statements (Europe) 
34
Safety Statements (Europe) 
26-36/37/39-45
RIDADR 
UN 3261 8 / PGII
WGK Germany 
3
RTECS 
SC4751000

Protocols & Articles

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

References

Set your institution to view full text papers.

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)

Loading...


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)

Loading...


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)

Loading...


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)

Loading...


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

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)

Loading...


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)

Loading...


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

Related Products

related product

Product #

Description

Add to Cart

08168 Timestrip Plus 8 °C

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?