Propiolic acid

Propiolic acid
Names


Preferred IUPAC name Prop-2-ynoic acid
Other names Propiolic acid (no longer recommended) Acetylene carboxylic acid Propargylic acid Acetylene mono-carboxylic acid
Identifiers
CAS Number	471-25-0^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:33199^N
ChEMBL	ChEMBL1213530^N
ChemSpider	9706^N
ECHA InfoCard	100.006.763
EC Number	207-437-8
KEGG	C00804^N
MeSH	C011537
PubChem	10110
InChI InChI=1S/C3H2O2/c1-2-3(4)5/h1H,(H,4,5)^N Key: UORVCLMRJXCDCP-UHFFFAOYSA-N^N InChI=1/C3H2O2/c1-2-3(4)5/h1H,(H,4,5) Key: UORVCLMRJXCDCP-UHFFFAOYAX
SMILES C#CC(=O)O
Properties
Chemical formula	C₃H₂O₂
Molar mass	70.05 g/mol
Density	1.1325 g/cm³
Melting point	9 °C (48 °F; 282 K)
Boiling point	144 °C (291 °F; 417 K) (decomposes)
Hazards
Safety data sheet	External MSDS
EU classification (DSD)	T+
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is ^YN ?)
Infobox references

Propiolic acid is the organic compound with the formula HC₂CO₂H. It is the simplest acetylenic carboxylic acid. It is a colourless liquid that crystallises to give silky crystals. Near its boiling point, it decomposes. It is soluble in water and possesses an odor like that of acetic acid.

It is prepared commercially by oxidizing propargyl alcohol at a lead electrode. It can also be prepared by decarboxylation of acetylenedicarboxylic acid.

Exposure to sunlight converts it into trimesic acid (benzene-1,3,5-tricarboxylic acid). It undergoes bromination to give dibromoacrylic acid. With hydrogen chloride it forms chloroacrylic acid. Its ethyl ester condenses with hydrazine to form pyrazolone.

It forms a characteristic explosive solid upon treatment to its aqueous solution with ammoniacal silver nitrate. An amorphous explosive precipitate forms with ammoniacal cuprous chloride.

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Wikipedia