Allyl phenyl ether

Allyl phenyl ether (C9H10O) is a clear and very slight yellow liquid that is stable under normal temperatures and pressures. For the most part it is a fairly stable compound, however if it decomposes, toxic fumes can be produced, such as carbon dioxide and carbon monoxide.[1]

Allyl phenyl ether
Names
Preferred IUPAC name
[(Prop-2-en-1-yl)oxy]benzene
Other names
(Allyloxy)benzene
3-Phenoxypropene
Allyloxybenzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.569
EC Number
  • 217-125-3
UNII
Properties
C9H10O
Molar mass 134.178 g·mol−1
Hazards
GHS pictograms
GHS Signal word Warning
H302, H312, H332
P261, P264, P270, P271, P280, P301+312, P302+352, P304+312, P304+340, P312, P322, P330, P363, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Allyl phenyl ether is a good starting reactant for many different experiments. One experiment that it is used for is the Claisen rearrangement. Due to its structure, it can carry out the rearrangement by being in the less optimal structure where the compound appears to be sterically hindered. This position is actually necessary and can only be formed by certain compounds like allyl phenyl ether.[2][3]

One type of synthesis of allyl phenyl ether is through tri-liquid phase catalysis, which uses the reagents of NaOPh (C6H5NaO) and tetra-n-butylammonium bromide. Some of the factors that affect the synthesis are:[4]

  • The amounts of different types of salt (NaBr, KBr, Na2CO3)
  • temperature
  • kinds of organic solvents used
  • mole fraction of NaOPh

References

  1. MSDS Allyl Phenyl Ether, Chemical Book http://www.chemicalbook.com/ProductMSDSDetailCB6454708_EN.htm
  2. Castro, Ana M. Martin. “Claisen Rearrangement over the Past Nine Decades” Chemical Reviews 104, no. 6 (2004): 2939-3006
  3. Yadav, G. D.; Lande, S. V., UDCaT-5: A Novel and Efficient Solid Superacid Catalyst for Claisen Rearrangement of Substituted Allyl Phenyl Ethers. Synthetic Communications 2007, 37 (6), 941-946
  4. Hsu-chin Hsiao, J. D.; Hung-shan Weng, J. D., ANALYSIS OF FACTORS AFFECTING THE SYNTHESIS OF ALLYL PHENYL ETHER BY TRI-LIQUID-PHASE CATALYSIS. Chemical Engineering Communications 2004, 191 (5), 705-717
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