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

EC Number |

* 217-125-3

PubChem CID

* 74458

UNII |

* 26S07OSX4O

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
Appearance  | colorless to yellowish liquid[1]
Boiling point |  191.7 °C (377.1 °F; 464.8 K)
Hazards
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H302, H312, H332

GHS precautionary statements

| 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

Tracking categories (test):

* SizeSet

Allyl phenyl ether is an organic compound with the formula C6H5OCH2CH=CH2. It is a colourless to yellowish liquid.

## Preparation

Allyl phenyl ether is prepared by the reaction of sodium phenoxide with allyl bromide:[2]

C6H5ONa + BrCH2CH=CH2 → C6H5OCH2CH=CH2 \+ NaBr

The yield is almost quantitative when the reaction is conducted in homogeneous solution using dimethoxyethane. When the reaction is conducted as a slurry in diethyl ether, the predominant product is, after acidic work-up, 2-allylphenol.

## Reactions

Allyl phenyl ether converts to 2-allylphenol in the presence of acid catalysts. This conversion is an example of the Claisen rearrangement.[3][4]

The Claisen rearrangement

## References

1. ↑ Sigma-Aldrich Co., Allyl phenyl ether. Retrieved on 2026-05-24.
2. ↑ Kornblum, Nathan; Lurie, Arnold P. (1959). "Heterogeneity as a Factor in the Alkylation of Ambident Anions: Phenoxide Ions1,2". Journal of the American Chemical Society 81 (11): 2705–2715. doi:10.1021/ja01520a030.
3. ↑ Martín Castro, Ana M. (2004). "Claisen Rearrangement over the Past Nine Decades". Chemical Reviews 104 (6): 2939–3002. doi:10.1021/cr020703u. PMID 15186185.
4. ↑ 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

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*[CID]: Compound ID
*[H302]: Harmful if swallowed
*[H312]: Harmful in contact with skin
*[H332]: Harmful if inhaled
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P271]: Use only outdoors or in a well-ventilated area
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P301+312]: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P304+312]: IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P322]: Specific measures (see … on this label)
*[P330]: Rinse mouth
*[P363]: Wash contaminated clothing before reuse
*[P501]: Dispose of contents/container to …