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4-Isopropenylphenol
| Column 1 | Column 2 |
|---|---|
| Preferred IUPAC name | |
| 4-(Prop-1-en-2-yl)phenol | |
| Other names | |
| p-Isopropenylphenol | |
| CAS Number | .mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}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,1H2,2H3Key: JAGRUUPXPPLSRX-UHFFFAOYSA-N | |
| SMILES | |
| CC(=C)C1=CC=C(C=C1)O | |
| Chemical formula | C9H10O |
| Molar mass | 134.178 g·mol−1 |
| Appearance | white solid |
| Melting point | 83 °C (181 °F; 356 K) |
| 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 | |
4-Isopropenylphenol is an organic compound with the formula .mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}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.
The high-temperature hydrolysis of BPA gives the title compound together with phenol:
(CH3)2C(C6H4OH)2 + H2O → CH2=(CH3)CC6H4OH + C6H5OH
The compound can also be produced by catalytic dehydrogenation of 4-isopropylphenol.
4-Isopropenylphenol undergoes O-protonation by sulfuric acid, giving the carbocation, which undergoes a variety of dimerization reactions.
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