Propiolic acid (Redirected from 2-Propynoic acid)

Propiolic acid
Names
Preferred IUPAC name
Prop-2-ynoic acid
Other names
Propiolic acid
Acetylene carboxylic acid
Propargylic acid
Acetylene mono-carboxylic acid
Identifiers
3D model (JSmol)
878176
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.763 Edit this at Wikidata
EC Number
  • 207-437-8
81893
KEGG
MeSH C011537
UNII
  • 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
  • C#CC(=O)O
Properties
C3H2O2
Molar mass 70.047 g·mol−1
Density 1.1325 g/cm3
Melting point 9 °C (48 °F; 282 K)
Boiling point 144 °C (291 °F; 417 K) (decomposes)
Acidity (pKa) pka = 1.89
Hazards
GHS labelling:
GHS02: FlammableGHS06: ToxicGHS07: Exclamation mark
Danger
H226, H301, H310, H315, H335
P210, P233, P240, P241, P242, P243, P261, P262, P264, P270, P271, P280, P301+P310, P302+P350, P302+P352, P303+P361+P353, P304+P340, P310, P312, P321, P322, P330, P332+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

Preparation

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

Reactions and applications

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.

Propiolates

Propiolates are esters or salts of propiolic acid. Common examples include methyl propiolate and ethyl propiolate.

See also


This page was last updated at 2023-11-22 00:10 UTC. Update now. View original page.

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