Skip to Content
Merck
All Photos(3)

Documents

232211

Sigma-Aldrich

4-Pentynoic acid

95%

Synonym(s):

Propargylacetic acid

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Linear Formula:
CH≡CCH2CH2COOH
CAS Number:
6089-09-4
Molecular Weight:
98.10
Beilstein:
1742047
EC Number:
228-028-0
MDL number:
MFCD00004407
UNSPSC Code:
12352100
PubChem Substance ID:
24853886
NACRES:
NA.22

Assay

95%

form

solid

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Palladium-catalyzed synthesis of new unsaturated exo-enol lactones with potential biological activity.
Bouyssi D, et al.
Tetrahedron Letters, 34(19), 3129-3130 (1993)
Xun Ji et al.
The Journal of organic chemistry, 78(9), 4312-4318 (2013-04-06)
An efficient and facile Au(I)/Ag(I)-catalyzed cascade method has been developed for one-pot synthesis of the complex polycyclic heterocycles benzo[4,5]imidazo[1,2-c]pyrrolo[1,2-a]quinazolinone derivatives through treatment of the substituted 2-(1H-benzo[d]imidazol-2-yl)anilines with 4-pentynoic acid or 5-hexynoic acid. The strategy features a Au(I)/Ag(I)-catalyzed one-pot cascade process
Tetrahedron Letters, 33, 2811-2811 (1992)
Thomas L Mindt et al.
The Journal of organic chemistry, 72(26), 10247-10250 (2007-11-30)
Alkynoic acids, in particular, 4-pentynoic acid derivatives, undergo intramolecular cyclizations to enol lactones under reaction conditions typically applied for the Cu(I)-catalyzed cycloaddition of terminal alkynes and azides (click chemistry). Starting from appropriate alkynoic acid derivatives, either enol lactones or 1,2,3-triazole
Thanh Tam Trinh et al.
Macromolecular rapid communications, 35(2), 141-145 (2013-12-18)
A library of eight sequence-defined model oligomers, whose sequence is based on a (0,1) binary code, is prepared through chemoselective repeating cycles of amidification and copper-assisted alkyne-azide cycloaddition reactions from a non-modified Wang resin. This library is constructed from two
View All Related Papers

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.

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.

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.

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.

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

Contact Technical Service