Propiolic acid
| Names | |
|---|---|
| Preferred IUPAC name
Prop-2-ynoic acid[1] | |
| Other names
Propiolic acid
Acetylene carboxylic acid Propargylic acid Acetylene mono-carboxylic acid | |
| Identifiers | |
3D model (JSmol)
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| 878176 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
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| EC Number |
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| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
| 81893 | |
| KEGG | |
| MeSH | C011537 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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 [2] |
| Hazards | |
| GHS labelling:[3] | |
| 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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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.[4][5]
Preparation
[edit | edit source]It is prepared commercially by oxidizing propargyl alcohol at a lead electrode.[6] It can also be prepared by decarboxylation of acetylenedicarboxylic acid.[citation needed]
Reactions and applications
[edit | edit source]Exposure to sunlight converts it into trimesic acid (benzene-1,3,5-tricarboxylic acid).[5] It undergoes bromination to give dibromoacrylic acid. With hydrogen chloride it forms chloroacrylic acid. Its ethyl ester condenses with hydrazine to form pyrazolone.[5]
It forms a characteristic explosive solid upon treatment to its aqueous solution with ammoniacal silver nitrate.[5] An amorphous explosive precipitate forms with ammoniacal cuprous chloride.
Propiolates
[edit | edit source]Propiolates are esters or salts of propiolic acid. Common examples include methyl propiolate and ethyl propiolate.
See also
[edit | edit source]References
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