4-Isopropenylphenol
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| Names | |
|---|---|
| Preferred IUPAC name
4-(Prop-1-en-2-yl)phenol | |
| Other names
p-Isopropenylphenol | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C9H10O | |
| Molar mass | 134.178 g·mol−1 |
| Appearance | white solid |
| Melting point | 83 °C (181 °F; 356 K) |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H302, H371 | |
| 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).
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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]