Phenyl methanesulfonate
[CAS# 16156-59-5]

Identification

• Classification: Organic raw materials >> Inorganic acid ester
• Name: Phenyl methanesulfonate
• Synonyms: Methanesulfonic acid, phenyl ester
• Molecular Formula: C₇H₈O₃S
• Molecular Weight: 172.20
• CAS Registry Number: 16156-59-5
• EC Number: 626-664-7
• SMILES: CS(=O)(=O)OC1=CC=CC=C1

Properties

• Melting point: 58-61 °C (Expl.)
• Boiling point: 279 °C (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Phenyl methanesulfonate is an organic compound known for its role as an electrophilic reagent in organic synthesis. It consists of a phenyl group attached to a methanesulfonate moiety, making it a reactive ester. This compound is valuable for introducing methanesulfonate groups into various substrates, facilitating reactions such as alkylations, substitutions, and the preparation of sulfonate esters. The structural combination of the phenyl ring and the methanesulfonate group enhances its stability while maintaining its reactivity, making it an effective intermediate in chemical transformations.

The discovery of phenyl methanesulfonate is tied to the broader exploration of sulfonate esters in the early 20th century. Researchers investigating the reactivity of sulfonic acid derivatives found that esters like methanesulfonates offered a unique balance of stability and leaving group ability. The synthesis of phenyl methanesulfonate involves reacting phenol with methanesulfonyl chloride in the presence of a base such as pyridine. This method ensures high yields and is widely used due to its straightforward procedure and reproducibility.

Phenyl methanesulfonate finds applications in synthetic chemistry, particularly in the field of nucleophilic substitution reactions. It serves as a useful intermediate for converting hydroxyl groups into better leaving groups, facilitating reactions with nucleophiles such as amines, thiols, and halides. This conversion is critical in the synthesis of pharmaceuticals, agrochemicals, and fine chemicals. Additionally, phenyl methanesulfonate is used in the preparation of sulfonate esters that are employed in various organic transformations, including the synthesis of ethers and other functionalized compounds.

This compound also plays a role in polymer chemistry, where sulfonate esters are used to modify polymer backbones, improving properties like solubility and reactivity. The controlled reactivity of phenyl methanesulfonate makes it suitable for selective functionalization processes, contributing to advances in material science and drug development.

Current research continues to explore the utility of phenyl methanesulfonate in novel synthetic methodologies and its potential in developing new materials and pharmaceutical agents. Its ability to act as an efficient leaving group ensures its relevance in modern organic synthesis.

References

2007. Reactions of Sulfonyl- or Silicon-Activated Phenols. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-031-00425

2007. Pd/C-Catalyzed Reduction of Aryl Sulfonates. Synfacts, 3(7), 0770.
DOI: 10.1055/s-2007-968486

2009. Hiyama Cross-Coupling of Aryl Mesylates. Synfacts, 5(3), 0332.
DOI: 10.1055/s-0028-1087649