Phenylpropiolic acid
title: "Phenylpropiolic acid" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["phenyl-compounds", "alkyne-derivatives", "carboxylic-acids"] topic_path: "general/phenyl-compounds" source: "https://en.wikipedia.org/wiki/Phenylpropiolic_acid" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 464201383 | Name = Phenylpropiolic acid | ImageFile = phenylpropiolic acid.png | ImageSize = | ImageName = Skeletal formula of phenylpropiolic acid | ImageFile1 = Phenylpropiolic-acid-3D-balls.png | ImageSize1 = 220px | ImageName1 = Ball-and-stick model | PIN = 3-Phenylprop-2-ynoic acid | OtherNames = Phenylpropynoic acid; Phenylpropiolic acid |Section1={{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 62682 | ChEBI_Ref = | ChEBI = 90355 | PubChem = 69475 | InChI = 1/C9H6O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,(H,10,11) | InChIKey = XNERWVPQCYSMLC-UHFFFAOYAX | StdInChI_Ref = | StdInChI = 1S/C9H6O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,(H,10,11) | StdInChIKey_Ref = | StdInChIKey = XNERWVPQCYSMLC-UHFFFAOYSA-N | CASNo_Ref = | CASNo = 637-44-5 | UNII_Ref = | UNII = 4KE28XZ9GX | SMILES = O=C(C#Cc1ccccc1)O |Section2={{Chembox Properties | Formula = C9H6O2 | MolarMass = 146.14 g/mol | Density = | MeltingPtC = 135 to 137 | MeltingPt_notes = | BoilingPt =
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.
References
References
- {{EB1911
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