What Is Phenyl Acetate?
Phenyl acetate is an organic compound, classified as one of the phenolic esters, having the structure of dehydration-condensation of acetic acid and phenol. Its molecular formula is C8H8O2, molecular weight is 136.15, density is approximately 1.08 g/ml, and the CAS number is 122-79-2.
Other names include phenol acetate and acetoxybenzene.
Properties of Phenyl Acetate
Phenyl acetate is a colorless liquid that exhibits a phenolic odor at room temperature and pressure. It is almost insoluble in water and soluble in organic solvents such as ethanol, chloroform, and ether. It is synthesized by the reaction of acetic anhydride or acetyl chloride with phenol. In this reaction, the nucleophilic nature of the oxygen atom of phenol is utilized. It is synthesized by reacting with acetic anhydride or acetyl chloride, which are susceptible to nucleophilic substitution reactions.
The boiling point of this substance is approximately 384.8 °F (196 °C), but its flash point is 201 °F (94 °C). At temperatures above 176 °F (80 °C), there is a risk of spontaneous ignition or explosion. Therefore, it should be handled in a closed system and ventilated thoroughly.
Since it is irritating to the skin and eyes, rubber gloves and protective eyewear should be worn when handling it.
Uses of Phenyl Acetate
Uses of phenyl acetate include use as a raw material for synthesizing various organic compounds, such as enzyme substrates and inhibitors. It is a relatively inexpensive reagent that is readily available. However, this substance is not often used on its own.
Phenyl acetate has a benzene ring structure with an ester group attached to it, allowing various modifications to be made to the benzene ring. Many of the transmitters in the human body have such a structure and are therefore used as raw materials for drugs that target these transmitters and receptors. Since this substance is a substrate for esterases, it is used as a raw material for esterase inhibitors.
Phenyl acetate also rearranges to 2- or 4-hydroxyphenyl methyl ketone in the presence of Lewis acids and is used as a raw material for the synthesis of various aromatic organic compounds, mainly as nitrophenyl phenyl derivatives. Since this substance is an ester, it is neither acidic nor basic, and there are no nucleophilic or electrophilic moieties, making it very easy to handle.
Other Information on Phenyl Acetate
Differences From Phenyl Acetate
It should be noted that the structural formula of phenyl acetate is CH3-COO-Ph, which is a different substance from phenyl acetate (Ph-CH2-COOH). Phenyl acetate has a carboxyl group and exhibits completely different properties.
About Phenyl Mercury Acetate
One substance with a very similar structure derived from phenyl acetate is phenyl mercury acetate. This substance is an organometallic compound with a mercury atom inserted between an oxygen atom and a carbon atom on the benzene ring.
Phenyl mercury acetate was registered as an agricultural chemical in 1948 as a special agent to kill rice blast fungus, but it expired in 1973. At the time, the toxicity of methylmercury, which caused Minamata disease, was a hot topic of public debate, and phenyl mercury acetate, an organic compound that also contains mercury, was no longer used due to social unrest over mercury compounds.
However, methyl mercury was not detected in phenyl mercury acetate, and no toxicity was noted. However, there have been cases of poisoning during experiments and cases of poisoning during pesticide spraying. It is now being substituted by other pesticides and is no longer used.
This compound can be synthesized by heat refluxing mercury(II) acetate with trifluorosilylbenzene in benzene or by reaction of diphenylmercury with acetic acid.