Name: China Supplier Best Price High Quality Methyl Benzoylformate CAS 15206-55-0
Brand: Wuhan Fortuna Chemical Co., Ltd.

Specifications of Methyl Benzoylformate CAS 15206-55-0

Items	Specification
Product name	Methyl benzoylformate
CAS	15206-55-0
Appearance	Light yellow liquid
Assay	≥99%
Molecular Formula	C9H8O3
Molecular weight	164.16
EINECS	239-263-3

Parameters of Methyl Benzoylformate CAS 15206-55-0

Product parameters
Cas number:	15206-55-0
Appearance:	Light yellow liquid
Purity:	99%min
Package details:	25kg/drum;200kg/drum
Brand:	Fortunachem

Methyl benzoylformate (Methyl phenylglyoxylate) is an organic ester with the chemical formula C₆H₅C(O)COOCH₃. Its structure consists of a benzoyl group (C₆H₅C(O)–) directly attached to a methoxyformyl group (–COOCH₃). This makes it the methyl ester of benzoylformic acid.

This structure classifies it as an alpha-keto ester, meaning it has a carbonyl group (C=O) directly adjacent to the ester functional group. This combination of two electron-withdrawing carbonyl groups makes it a highly reactive and versatile synthetic building block.

Key Properties

Appearance: A clear, pale yellow to yellow liquid.
Odor: Often described as having a strong, pungent, aromatic odor.
Reactivity: The central reactivity stems from the two adjacent carbonyl groups. The keto group (C=O) is highly electrophilic, making it susceptible to nucleophilic attack. The ester group can be hydrolyzed or transformed. This bifunctional nature is key to its utility.
Chirality: While the molecule itself is not chiral, it is a prime substrate for reactions that create new chiral centers, making it valuable in asymmetric synthesis.

Primary Applications in Organic Synthesis

Methyl benzoylformate's primary value lies in its role as a versatile chemical intermediate or synthon for constructing more complex molecules.

1. As a Precursor to α-Hydroxy and α-Amino Esters

This is one of its most important uses. The highly electrophilic keto group can be reduced or aminated.

Reduction: It can be reduced enantioselectively (e.g., using biocatalysts or chiral metal catalysts) to produce mandelic acid esters. Mandelic acid and its derivatives are valuable as pharmaceuticals, resolving agents, and in cosmetics.
Amination: It undergoes reductive amination to form phenylglycine esters. Phenylglycine is a crucial building block in the synthesis of beta-lactam antibiotics (e.g., penicillins, cephalosporins) and other drugs.

2. Photoinitiator

Methyl benzoylformate is an effective photoinitiator for radical polymerization, particularly in UV-curable inks, coatings, and adhesives.

Mechanism: Upon exposure to UV light, it undergoes an α-cleavage (Norrish Type I reaction), generating two free radical species: a benzoyl radical and a methoxycarbonyl radical. These highly reactive radicals initiate the polymerization chain reaction of monomers like acrylates, causing the liquid resin to harden into a solid plastic film almost instantly.

3. Building Block for Heterocycles

Its reactive keto group allows it to participate in cyclization reactions with various nucleophiles (e.g., hydrazines, hydroxylamine, ureas) to form a wide range of nitrogen- and oxygen-containing heterocyclic compounds, which are common structures in many pharmaceuticals and agrochemicals.

4. Use in the Sharpless Asymmetric Dihydroxylation

It serves as a benchmark and standard substrate for testing and optimizing the Sharpless asymmetric dihydroxylation reaction, a Nobel Prize-winning method for converting alkenes into chiral vicinal diols.

Safety and Handling

Irritant: It is a strong irritant to the skin, eyes, and respiratory system.
Lachrymator: Its vapors may cause tearing (it is a lachrymator).
Sensitization: Repeated exposure can lead to skin sensitization (allergic reactions).
PPE: Handling requires strict precautions: chemical safety goggles, gloves, and adequate ventilation (a fume hood is highly recommended).
Storage: It should be stored in a cool, dark place, as it can be light-sensitive due to its role as a photoinitiator.

Summary

In summary, Methyl benzoylformate is a highly reactive alpha-keto ester that serves as a cornerstone intermediate in synthetic organic chemistry. Its two primary roles are:

Chemical Synthesis: As a precursor to important chiral building blocks like mandelate and phenylglycine esters for the pharmaceutical industry.

Industrial Application: As an efficient photoinitiator in UV-curing polymer technology.

Its value is derived from the high electrophilicity of its carbonyl group, which allows it to participate in a wide array of transformations, making it a powerful tool for chemists.