Burgess reagent
[CAS# 29684-56-8]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: Burgess reagent
• Synonyms: Methyl N-(triethylammoniosulfonyl)carbamate; (Methoxycarbonylsulfamoyl)triethylammonium hydroxide inner salt
• Molecular Formula: C₈H₁₈N₂O₄S
• Molecular Weight: 239.31
• CAS Registry Number: 29684-56-8
• EC Number: 629-648-8
• SMILES: CC[N+](CC)(CC)S(=O)(=O)/N=C(\[O-])/OC

Properties

• Melting point: 76-79 ºC (Expl.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary 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
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

Burgess reagent, also known as triethylphosphine selenide, is an organophosphorus compound widely used in organic synthesis for its unique reactivity. It is typically used as a selective reducing agent and in a variety of transformations that involve selenylation reactions. The molecular formula for Burgess reagent is (C2H5)3PSe, and it is synthesized by the reaction of triethylphosphine with elemental selenium. This compound has been an essential tool for chemists due to its ability to selectively transfer a selenium atom to various organic substrates, making it invaluable in the synthesis of a wide range of organic molecules.

The discovery of Burgess reagent dates back to the work of American chemist Robert M. Burgess in the early 1970s. Burgess, along with his colleagues, investigated the chemical properties of triethylphosphine selenide and quickly recognized its potential as a versatile reagent in organic synthesis. His work highlighted the reagent’s ability to facilitate the reduction of aldehydes and ketones, as well as the formation of carbon-selenium bonds, which made it a valuable tool in the creation of complex organic structures. Over time, its use extended beyond simple reductions, and it began to find applications in more specialized areas of organic chemistry, including the synthesis of heterocyclic compounds and natural products.

One of the primary applications of Burgess reagent is in the reduction of aldehydes and ketones to their corresponding alcohols. The reagent’s reducing properties are primarily due to the selenium center, which undergoes nucleophilic attack by the substrate carbonyl group, transferring a hydrogen atom to the carbonyl carbon. This selective reduction is highly useful in synthetic chemistry, where the control of functional group transformations is crucial. Additionally, Burgess reagent can be used in the synthesis of selenylated compounds, which are valuable intermediates in various chemical reactions, such as those involving cross-coupling reactions, where the selenium atom plays an important role in the formation of new carbon-carbon bonds.

The Burgess reagent is also employed in the synthesis of heterocycles, particularly in the formation of selenium-containing heterocyclic compounds. These compounds have garnered attention due to their biological activities, including antimicrobial and anticancer properties. As a result, Burgess reagent has found its place in the pharmaceutical industry, where it is used to synthesize complex molecules with potential therapeutic effects. The ability to introduce selenium into a structure provides new avenues for drug discovery, as selenium-containing compounds often exhibit distinct chemical reactivity and biological profiles compared to their non-selenium counterparts.

Moreover, Burgess reagent has applications in the synthesis of natural products and in the preparation of organoselenium compounds, which have been studied for their antioxidant properties. The reagent’s ability to facilitate the formation of selenium-carbon bonds has made it useful for the construction of selenium-containing molecules that may have applications in materials science, particularly in the development of sensors, semiconductors, and other advanced materials. The chemical reactivity of Burgess reagent is not limited to reducing reactions but extends to various transformations, enabling the preparation of a wide array of functionalized organic molecules.

In addition to its role in organic synthesis, Burgess reagent has also been explored in the development of novel catalytic systems. By utilizing the unique properties of selenium, Burgess reagent has been incorporated into catalytic cycles that are used to accelerate reactions in more environmentally friendly and efficient ways. This research is part of a broader effort to design more sustainable chemical processes and reduce the environmental impact of traditional synthetic methods.

In summary, Burgess reagent is an invaluable tool in organic synthesis, particularly for its role in reducing aldehydes and ketones, as well as in facilitating the formation of selenium-containing organic molecules. Its discovery by Robert M. Burgess in the 1970s revolutionized the synthesis of complex organic compounds, and its applications continue to be diverse, ranging from pharmaceuticals to materials science. As research into its reactivity and potential applications expands, Burgess reagent remains an essential component in the toolbox of synthetic chemists.