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232211 Sigma-Aldrich

4-Pentynoic acid

95%

Synonym: Propargylacetic acid

  • CAS Number 6089-09-4

  • Linear Formula CH≡CCH2CH2COOH

  • Molecular Weight 98.10

  •  Beilstein/REAXYS Number 1742047

  •  EC Number 228-028-0

  •  MDL number MFCD00004407

  •  PubChem Substance ID 24853886

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, C1 to C5, Carbonyl Compounds, Carboxylic Acids, Chemical Synthesis,
Quality Level   200
assay   95%
bp   110 °C/30 mmHg (lit.)
mp   54-57 °C (lit.)
storage temp.   2-8°C
SMILES string   OC(=O)CCC#C
InChI   1S/C5H6O2/c1-2-3-4-5(6)7/h1H,3-4H2,(H,6,7)
InChI key   MLBYLEUJXUBIJJ-UHFFFAOYSA-N

Description

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.

Application

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

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS05  GHS05
Signal word 
Danger
Hazard statements 
RIDADR 
UN 3261 8 / PGII
WGK Germany 
WGK 3
RTECS 
SC4751000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
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

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

Peer-Reviewed Papers
15

References

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