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303666

Sigma-Aldrich

2-Butynoic acid

98%

Synonym(s):

Tetrolic acid

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About This Item

Linear Formula:
CH3C≡CCO2H
CAS Number:
590-93-2
Molecular Weight:
84.07
EC Number:
209-695-7
MDL number:
MFCD00004363
UNSPSC Code:
12352100
PubChem Substance ID:
24858137
NACRES:
NA.22

Assay

98%

form

solid

mp

78-80 °C (lit.)

functional group

carboxylic acid

SMILES string

CC#CC(O)=O

InChI

1S/C4H4O2/c1-2-3-4(5)6/h1H3,(H,5,6)

InChI key

LUEHNHVFDCZTGL-UHFFFAOYSA-N

Related Categories

General description

The rotational spectrum of 2-butynoic acid was measured by pulsed supersonic-jet Fourier transform microwave spectroscopy.

Application

2-Butynoic acid was employed as synthon in a variety of reactions, including cycloacylation of phenols to flavones and chromones, and cyclization to γ-butyrolactones. It was also used in synthesis of Z-trisubstituted olefins via γ-alkylation.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCF4614
SHBJ6537
SHBF8855V
SHBD8128V
SHBD3499V

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The Journal of Organic Chemistry, 56, 5120-5120 (1991)
S Parveen et al.
Chemical communications (Cambridge, England), (12)(12), 1531-1533 (2005-03-17)
The application of FTIR spectroscopy to concentrated solutions of tetrolic acid shows, for the first time, a direct relationship between molecular self association in solution and H-bonded motifs in the subsequently crystallised solid phases.
gamma.-Alkylation of 2-butynoic acid. Route to controlled prenol homologation.
Pitzele BS, et al.
The Journal of Organic Chemistry, 40(2), 269-270 (1975)
Almost free methyl top internal rotation: Rotational spectrum of 2-butynoic acid.
Ilyushin V, et al.
Journal of Molecular Spectroscopy, 267(1), 186-190 (2011)
The Journal of Organic Chemistry, 55, 4349-4349 (1990)
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