Diethyl (tosyloxy)methylphosphonate
[CAS# 31618-90-3]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Diethyl (tosyloxy)methylphosphonate
• Synonyms: Diethyl [[(p-toluenesulfonyl)oxy]methyl]phosphonate; Diethyl [[[(4-tolyl)sulfonyl]oxy]methyl]phosphonate; Diethyl p-tosyloxymethylphosphonate; Tosyloxymethyl diethyl phosphonate; [[[(4-Tolyl)sulfonyl]oxy]methyl]phosphonic acid diethyl ester
• Molecular Formula: C₁₂H₁₉O₆PS
• Molecular Weight: 322.31
• CAS Registry Number: 31618-90-3
• EC Number: 608-653-9
• SMILES: CCOP(=O)(COS(=O)(=O)C1=CC=C(C=C1)C)OCC

Properties

• Density: 1.255±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.498, Calc.^*
• Boiling Point: 441.7±28.0 °C (760 mmHg), Calc.^*
• Flash Point: 220.9±24.0 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H332-H335
• Safety Statements: P261-P280-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H312
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	4	H332
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412

Discovery and Applications

Diethyl (tosyloxy)methylphosphonate is an organic compound with the chemical formula C9H13O5PS. It consists of a methylphosphonate group attached to a tosyl group (p-toluenesulfonyl group) via an oxygen atom. This compound is often used as a reagent in organic synthesis, particularly in the preparation of other phosphorus-containing compounds. The tosyl group is known for enhancing the reactivity of the compound, making it an important intermediate in the creation of more complex molecules.

The discovery of diethyl (tosyloxy)methylphosphonate is tied to the ongoing development of organophosphorus chemistry, which has been a field of significant interest due to the biological activity of many phosphorus-containing compounds. The inclusion of the tosyl group allows the compound to undergo nucleophilic substitution reactions more readily, making it a useful building block in the synthesis of a variety of other chemical substances.

This chemical compound finds applications in several areas of chemistry, most notably in the synthesis of organophosphorus compounds. It serves as an important intermediate in the preparation of phosphonate derivatives, which are utilized in agrochemicals, pharmaceuticals, and materials science. Phosphonates are known for their ability to bind to metal ions and their use in catalysis, water treatment, and flame retardant technologies.

One of the most significant applications of diethyl (tosyloxy)methylphosphonate is in the preparation of chemical agents that are used in the development of chemical warfare agents. Phosphonate derivatives have been studied for their ability to inhibit acetylcholinesterase, an enzyme critical for nerve function. Due to their toxicity, many phosphonate compounds are under strict regulation. However, these compounds also play a critical role in research aimed at developing treatments for nerve agent exposure and other biological threats.

In addition to its use in the synthesis of nerve agent precursors, diethyl (tosyloxy)methylphosphonate is employed in the development of new pharmaceuticals. Its ability to form stable bonds with biologically relevant targets makes it a valuable reagent for medicinal chemistry, particularly in the design of enzyme inhibitors and other biologically active molecules.

The compound is also used in the preparation of flame retardants. Organophosphorus compounds are known for their ability to suppress combustion, and diethyl (tosyloxy)methylphosphonate serves as a starting material for the synthesis of such fire-resistant chemicals. These applications highlight the versatility of diethyl (tosyloxy)methylphosphonate in both industrial and research settings.

References

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