Chemistry:4-Isopropenylphenol
From HandWiki
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| Names | |
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| Preferred IUPAC name
4-(Prop-1-en-2-yl)phenol | |
| Other names
p-Isopropenylphenol
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
PubChem CID
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| UNII | |
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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 pictograms |  
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| GHS Signal word | Warning |
| H302, H371 | |
| P260, P264, P270, P301+317Script error: No such module "Preview warning".Category:GHS errors, P308+316Script error: No such module "Preview warning".Category:GHS errors, 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 | |
Tracking categories (test):
4-Isopropenylphenol is an organic compound with the formula CH
2=(CH
3)CC
6H
4OH. 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]
Synthesis and reactions
The high-temperature hydrolysis of BPA gives the title compound together with phenol:[2]
- (CH
3)
2C(C
6H
4OH)
2 + H
2O → CH
2=(CH
3)CC
6H
4OH + C
6H
5OH
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]
References
- ↑ de Angelis, A.; Ingallina, P.; Perego, C. (2004). "Solid Acid Catalysts for Industrial Condensations of Ketones and Aldehydes with Aromatics". Industrial & Engineering Chemistry Research 43 (5). doi:10.1021/ie030429+.
- ↑ Hunter, Shawn E.; Felczak, Claire A.; Savage, Phillip E. (2004). "Synthesis of p-isopropenylphenol in high-temperature water". Green Chemistry 6 (4): 222. doi:10.1039/b313509h.
- ↑ Corson, B. B.; Heintzelman, W. J.; Schwartzman, L. H.; Tiefenthal, H. E.; Lokken, R. J.; Nickels, J. E.; Atwood, G. R.; Pavlik, F. J. (1958). "Preparation of Vinylphenols and Isopropenylphenols". The Journal of Organic Chemistry 23 (4): 544–549. doi:10.1021/jo01098a012.
- ↑ Chen, Wei-Fu; Lin, Hsing-Yo; Dai, Shenghong A. (2004). "Generation and Synthetic Uses of Stable 4-[2-Isopropylidene]-phenol Carbocation from Bisphenol A". Organic Letters 6 (14): 2341–2343. doi:10.1021/ol0493305. PMID 15228274.
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