232211

4-Pentynoic acid

95%

• Synonym(s): Propargylacetic acid
• Linear Formula: CH≡CCH₂CH₂COOH
• CAS Number: 6089-09-4
• Molecular Weight: 98.10
• Beilstein/REAXYS Number: 1742047
• EC Number: 228-028-0
• MDL number: MFCD00004407
• UNSPSC Code: 12352100
• PubChem Substance ID: 24853886
• NACRES: NA.22

Properties

• Quality Level: 200
• assay: 95%
• form: solid
• bp: 110 °C/30 mmHg (lit.)
• mp: 54-57 °C (lit.)
• functional group: carboxylic acid
• 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

Safety Information

• pictograms: GHS05
• signalword: Danger
• hcodes: H314
• pcodes: P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363
• Hazard Classifications: Skin Corr. 1B
• Storage Class: 8A - Combustible corrosive hazardous materials
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges