Phenylpropiolic acid

Phenylpropiolic acid
Names
	Preferred IUPAC name 3-Phenylprop-2-ynoic acid
	Other names Phenylpropynoic acid; Phenylpropiolic acid
Identifiers
CAS Number	637-44-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:90355 ;
ChemSpider	62682 ;
ECHA InfoCard	100.010.260
PubChem CID	69475;
UNII	4KE28XZ9GX ;
CompTox Dashboard (EPA)	DTXSID7060918 ;
	InChI InChI=1S/C9H6O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,(H,10,11) Key: XNERWVPQCYSMLC-UHFFFAOYSA-N ; InChI=1/C9H6O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,(H,10,11) Key: XNERWVPQCYSMLC-UHFFFAOYAX;
	SMILES O=C(C#Cc1ccccc1)O;
Properties
Chemical formula	C9H6O2
Molar mass	146.14 g/mol
Melting point	135 to 137 °C (275 to 279 °F; 408 to 410 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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.^[1]

References

^ This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). "Propiolic Acid". Encyclopædia Britannica. Vol. 22 (11th ed.). Cambridge University Press. p. 449.

[1] This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). "Propiolic Acid". Encyclopædia Britannica. Vol. 22 (11th ed.). Cambridge University Press. p. 449.

[1]