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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

Quality Level

100

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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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)
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)
Jie Chen et al.
The journal of physical chemistry. B, 112(26), 7794-7802 (2008-06-06)
The solution behavior of a model compound, tetrolic acid (TTA), is studied via molecular dynamics simulations in four organic solvents. The results suggest that strong interactions between TTA and solvent molecules (ethanol or dioxane) prevent the formation of carboxylic acid
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.
I A Mjör et al.
Journal of dental research, 61(8), 967-972 (1982-08-01)
Adhesive bonding of resins to dentin surfaces requires the removal of the layer of debris caused by the cutting. Certain isotonic acidic solutions can do this rapidly. Five solutions were evaluated using cell cultures and pulp studies in monkeys. At
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