4-Isopropenylphenol

4-Isopropenylphenol is an organic compound with the formula CH₂=(CH₃)CC₆H₄OH. The molecule consists of a 2-propenyl group (CH₂=C-CH₃) affixed to the 4 position of phenol. The compound is an intermediate in the production of bisphenol A (BPA), 2.7 Mkg/y of which are produced annually (2007). It is also generated by the recycling of o,p-BPA, a byproduct of the production of the p,p-isomer of BPA.^[1]

4-Isopropenylphenol

Names
Preferred IUPAC name 4-(Prop-1-en-2-yl)phenol
Other names p-Isopropenylphenol
Identifiers
CAS Number	4286-23-1 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL277808
ChemSpider	507836
PubChem CID	584247
UNII	2QP218C90D
CompTox Dashboard (EPA)	DTXSID90962744
InChI InChI=1S/C9H10O/c1-7(2)8-3-5-9(10)6-4-8/h3-6,10H,1H2,2H3 Key: JAGRUUPXPPLSRX-UHFFFAOYSA-N
SMILES CC(=C)C1=CC=C(C=C1)O
Properties
Chemical formula	C9H10O
Molar mass	134.178 g·mol−1
Appearance	white solid
Melting point	83 °C (181 °F; 356 K)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H371
Precautionary statements	P260, P264, P270, P301+P317, P308+P316, P330, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Synthesis and reactions

The high-temperature hydrolysis of BPA gives the title compound together with phenol:^[2]

(CH₃)₂C(C₆H₄OH)₂ + H₂O → CH₂=(CH₃)CC₆H₄OH + C₆H₅OH

The compound can also be produced by catalytic dehydrogenation of 4-isopropylphenol.^[3]

4-Isopropenylphenol undergoes O-protonation by sulfuric acid, giving the carbocation, which undergoes a variety of dimerization reactions.^[4]