Allyl phenyl ether

Allyl phenyl ether
Names
	Preferred IUPAC name [(Prop-2-en-1-yl)oxy]benzene
	Other names (Allyloxy)benzene; 3-Phenoxypropene; Allyloxybenzene
Identifiers
CAS Number	1746-13-0;
3D model (JSmol)	Interactive image;
ChemSpider	21159535;
ECHA InfoCard	100.015.569
EC Number	217-125-3;
PubChem CID	74458;
UNII	26S07OSX4O;
CompTox Dashboard (EPA)	DTXSID6061943 ;
	InChI InChI=1S/C9H10O/c1-2-8-10-9-6-4-3-5-7-9/h2-7H,1,8H2 COPY Key: POSICDHOUBKJKP-UHFFFAOYSA-N;
	SMILES C=CCOc1ccccc1;
Properties
Chemical formula	C9H10O
Molar mass	134.178 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H332
Precautionary statements	P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, 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 (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 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

^ MSDS Allyl Phenyl Ether, Chemical Book http://www.chemicalbook.com/ProductMSDSDetailCB6454708_EN.htm
^ Castro, Ana M. Martin. “Claisen Rearrangement over the Past Nine Decades” Chemical Reviews 104, no. 6 (2004): 2939-3006
^ 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
^ 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

[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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