Tetraethyl methylenediphosphonate
[CAS# 1660-94-2]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> BOC-amino acid
• Name: Tetraethyl methylenediphosphonate
• Molecular Formula: C₉H₂₂O₆P₂
• Molecular Weight: 288.21
• CAS Registry Number: 1660-94-2
• EC Number: 216-764-5
• SMILES: CCOP(=O)(CP(=O)(OCC)OCC)OCC

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*, 1.162 g/mL (Expl.)
• Index of Refraction: 1.428, Calc.^*, 1.442(Expl,)
• Boiling Point: 319.9±0.0 ºC (760 mmHg), Calc.^*, 171-174 ºC (Expl.)
• Flash Point: 185.9±43.5 ºC, Calc.^*

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

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
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

Tetraethyl methylenediphosphonate is an organic phosphorus compound that contains two phosphonate groups connected by a methylene bridge. The compound belongs to the family of organophosphonates, which are known for their diverse chemical reactivity and applications in various fields such as agriculture, medicine, and industrial chemistry. Tetraethyl methylenediphosphonate is commonly synthesized for use as a precursor in the preparation of more complex phosphonates or as a reagent in specific chemical reactions.

The discovery of tetraethyl methylenediphosphonate is part of the broader exploration of organophosphorus chemistry. Phosphonates, and particularly methylenediphosphonates, gained interest due to their unique structural features and potential applications. The methylene bridge between the two phosphonate groups imparts a special reactivity to these compounds, which makes them valuable in various chemical processes. Research into these compounds began in the mid-20th century when scientists began to investigate the synthetic potential of organophosphorus compounds, many of which exhibit beneficial properties such as high stability and solubility in organic solvents.

The synthesis of tetraethyl methylenediphosphonate typically involves the reaction of phosphorus trichloride or other phosphorus halides with an alcohol or a suitable reactant. One common method for its synthesis involves the condensation of phosphorous acid with chloroethanol, followed by further steps to ensure the desired ethyl groups are introduced at the phosphonate positions. The purity of the synthesized compound is generally ensured through techniques such as distillation and chromatography. These synthetic methods allow for the large-scale production of tetraethyl methylenediphosphonate, which can then be used in a variety of applications.

Tetraethyl methylenediphosphonate has several important applications, particularly in the fields of organic synthesis and catalysis. One of the primary uses of this compound is as a reagent in the preparation of other phosphonate derivatives. Its ability to introduce two phosphonate groups with a methylene bridge is crucial in the synthesis of more complex molecules, including those with potential pharmaceutical or agricultural uses. Additionally, tetraethyl methylenediphosphonate is used in the development of chemical agents that can act as scale inhibitors, dispersants, and corrosion inhibitors, particularly in systems where the presence of phosphonates provides an advantage in preventing the deposition of calcium salts or other mineral scales.

In the field of agriculture, tetraethyl methylenediphosphonate is used as a precursor for the synthesis of herbicides and pesticides. The presence of phosphonate groups in the molecule imparts herbicidal activity, which has been leveraged in the development of crop protection agents. These applications are particularly valuable in maintaining the health of crops by preventing the growth of unwanted weeds and pests that can hinder agricultural productivity.

In conclusion, tetraethyl methylenediphosphonate is an important compound in organophosphorus chemistry with a range of applications in organic synthesis, agriculture, and industrial processes. Its chemical structure and reactivity make it a valuable building block for the synthesis of more complex molecules, and it plays a key role in the development of herbicides, scale inhibitors, and other specialized chemicals.