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232211

Sigma-Aldrich

4-Pentynoic acid

95%

Synonyme(s) :

Propargylacetic acid

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About This Item

Formule linéaire :
CH≡CCH2CH2COOH
Numéro CAS:
6089-09-4
Poids moléculaire :
98.10
Numéro Beilstein :
1742047
Numéro CE :
228-028-0
Numéro MDL:
MFCD00004407
Code UNSPSC :
12352100
ID de substance PubChem :
24853886
Nomenclature NACRES :
NA.22

Pureté

95%

Forme

solid

Point d'ébullition

110 °C/30 mmHg (lit.)

Pf

54-57 °C (lit.)

Température de stockage

2-8°C

Chaîne SMILES 

OC(=O)CCC#C

InChI

1S/C5H6O2/c1-2-3-4-5(6)7/h1H,3-4H2,(H,6,7)

Clé InChI

MLBYLEUJXUBIJJ-UHFFFAOYSA-N

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Description générale

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

Pictogrammes

Corrosion
GHS05

Mention d'avertissement

Danger

Mentions de danger

H314

Classification des risques

Skin Corr. 1B

Code de la classe de stockage

8A - Combustible corrosive hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificats d'analyse (COA)

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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
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