Phenylpropiolic acid

Phenylpropiolic acid
IUPAC name Phenylpropynoic acid
Other names Phenylpropiolic acid
Identifiers
CAS number	637-44-5
PubChem	69475
ChemSpider	62682 Y
Jmol-3D images	Image 1
SMILES O=C(C#Cc1ccccc1)O
InChI InChI=1S/C9H6O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,(H,10,11) Y Key: XNERWVPQCYSMLC-UHFFFAOYSA-N Y InChI=1/C9H6O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,(H,10,11) Key: XNERWVPQCYSMLC-UHFFFAOYAX
Properties
Molecular formula	C9H6O2
Molar mass	146.14 g/mol
Melting point	135–137 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox 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, C₆H₅CH₂CH₂CO₂H. 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 a publication now in the public domain: Chisholm, Hugh, ed. (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press.