Phenylpropiolic acid

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Phenylpropiolic acid

IUPAC name	Phenylpropynoic acid
Other names	Phenylpropiolic acid
Identifiers
CAS number	[637-44-5]
SMILES	OC(C#Cc1ccccc1)=O
Properties
Molecular formula	C₉H₆O₂
Molar mass	146.14 g/mol
Density	? g/cm³
Melting point	135-137 °C
Boiling point	°C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Phenylpropiolic acid, C₆H5CCCO₂H, formed by the action of alcoholic potash on cinnamic acid dibromide, C₆H₅CHBrCHBrCO₂H, crystallizes in long needles or prisms which melt at 136–137 °C. When heated with water to 120 °C, it yields phenylacetylene (C₆H₅CCH). Chromic acid oxidizes it to benzoic acid; zinc and acetic acid reduce it to cinnamic acid, C₆H₅CH=CHCO₂H, whilst sodium amalgam reduces it to hydrocinnamic acid, C₆H₅CH₂CO₂H. Ortho-nitrophenylpropiolic acid, NO₂C₆H₄CCCO₂H, prepared by the action of alcoholic potash on ortho-nitrocinnamic acid dibromide, crystallizes in needles which decompose when heated to 155–156 °C. It is readily converted into indigo.

This article incorporates text from the Encyclopædia Britannica Eleventh Edition, a publication now in the public domain.

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