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4-Isopropenylphenol

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4-Isopropenylphenol
Names
Preferred IUPAC name 4-(Prop-1-en-2-yl)phenol
Other names p-Isopropenylphenol
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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
Properties
Chemical formula C9H10O
Molar mass 134.178 g·mol
Appearance white solid
Melting point 83 °C (181 °F; 356 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation markGHS08: Health hazard
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 , 100 kPa). Infobox references
Chemical compound

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.

Synthesis and reactions

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.

References

  1. 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+.
  2. 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.
  3. 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.
  4. 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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