Methyl benzoylformate
[CAS# 15206-55-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Methyl ester compound
• Name: Methyl benzoylformate
• Synonyms: Methyl phenylglyoxylate
• Molecular Formula: C₉H₈O₃
• Molecular Weight: 164.16
• CAS Registry Number: 15206-55-0
• EC Number: 239-263-3
• SMILES: COC(=O)C(=O)C1=CC=CC=C1

Properties

• Density: 1.161 g/mL (4 °C)
• Melting point: 16 °C
• Boiling point: 246-248 °C
• Refractive index: 1.525-1.527
• Flash point: 113 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H317-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P272-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Methyl benzoylformate is an organic compound with notable applications in the field of organic synthesis and industrial chemistry. This substance, with the chemical formula C15H12O3, is derived from the esterification of benzoylformic acid with methanol. The structure of methyl benzoylformate includes a benzoyl group attached to a formate ester, which imparts unique reactivity and versatility to the compound.

The discovery of methyl benzoylformate can be linked to advancements in the synthesis of esters and their applications in various chemical processes. The compound is typically synthesized through the reaction of benzoylformic acid with methanol in the presence of an acid catalyst. This reaction produces methyl benzoylformate along with water as a byproduct. The esterification process allows for the formation of a compound with both aromatic and formyl functionalities, enhancing its utility in different chemical contexts.

One of the primary applications of methyl benzoylformate is in the field of organic synthesis as a reagent. Its ability to act as an electrophile makes it useful in the formation of various chemical intermediates. For instance, methyl benzoylformate can participate in Friedel-Crafts acylation reactions, where it reacts with aromatic compounds to form substituted ketones. This reaction is valuable in the synthesis of complex organic molecules used in pharmaceuticals and agrochemicals.

In addition to its role in organic synthesis, methyl benzoylformate is employed in the production of fragrances and flavor compounds. The compound's aromatic benzoyl group contributes to its desirable scent properties, making it a useful ingredient in the formulation of perfumes and flavoring agents. Its inclusion in these products enhances their aromatic profile and contributes to the overall sensory experience.

Another notable application of methyl benzoylformate is in the production of polymer materials. The compound can be used as a monomer or co-monomer in the polymerization process to introduce benzoyl and formyl groups into the polymer structure. This incorporation can modify the polymer's properties, such as its thermal stability, solubility, and reactivity, making it suitable for specific industrial applications.

Despite its beneficial uses, handling and safety considerations are important when working with methyl benzoylformate. As with many organic compounds, it is essential to follow appropriate safety protocols and guidelines to minimize exposure and ensure safe handling.

Overall, methyl benzoylformate is a valuable compound with diverse applications in organic synthesis, fragrance production, and polymer chemistry. Its unique chemical structure and reactivity make it an important ingredient in various industrial and commercial products.

References

2024. Radical intermediates in the photolysis of the mixed benzoyl-substituted phosphonium-iodonium ylide in different solvents. Russian Chemical Bulletin, 73, 807-814.
DOI: 10.1007/s11172-024-4161-6

2020. Study of three-component reaction of μ-ketoesters and active methylenes with OH-acids to synthesize new 2-amino-4H-pyran derivatives and evaluation of their antibacterial and antioxidant activities. Research on Chemical Intermediates, 46, 1653-1667.
DOI: 10.1007/s11164-019-04066-x

2021. Design, synthesis, and biological evaluation of phenyloxadiazole derivatives as potential antifungal agents against phytopathogenic fungi. Monatshefte für Chemie - Chemical Monthly, 152, 339-348.
DOI: 10.1007/s00706-020-02717-z