Bis(dichlorophosphoryl)methane
[CAS# 1499-29-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphorous compound
• Name: Bis(dichlorophosphoryl)methane
• Synonyms: ^*Calculated using Advanced Chemistry Development (ACD/Labs) Software.
• Molecular Formula: CH₂Cl₄O₂P₂
• Molecular Weight: 249.78
• CAS Registry Number: 1499-29-2
• EC Number: 627-821-2
• SMILES: C(P(=O)(Cl)Cl)P(=O)(Cl)Cl

Properties

• Density: 1.8±0.1 g/cm³, Calc.^*
• Melting point: 102-104 °C (Expl.)
• Index of Refraction: 1.485, Calc.^*
• Boiling Point: 329.0±25.0 °C (760 mmHg), Calc.^*
• Flash Point: 152.8±23.2 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H314-H318
• Safety Statements: P260-P264-P264+P265-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1B	H314

Discovery and Applications

Bis(dichlorophosphoryl)methane is a phosphorus-containing organic compound with the formula (Cl2PO)2CH2. This molecule consists of a central methylene group bonded to two dichlorophosphoryl groups. It is known for its utility as a reagent in organophosphorus chemistry due to its unique structure and reactivity. The presence of both phosphoryl and chlorinated groups allows it to participate in a variety of chemical transformations, particularly those involving the introduction of phosphorus-containing moieties.

The discovery of bis(dichlorophosphoryl)methane dates back to the mid-20th century, when researchers were exploring new ways to incorporate phosphorus into organic molecules. Early synthetic efforts focused on the reaction of dichlorophosphoryl chloride (Cl2POCl) with methylene sources under controlled conditions. These investigations provided key insights into the reactivity and stability of the molecule, establishing it as a versatile intermediate in phosphorus chemistry.

A typical synthesis of bis(dichlorophosphoryl)methane involves the reaction of dichloromethane (CH2Cl2) with phosphorus pentachloride (PCl5) and phosphorus oxychloride (POCl3). The reaction proceeds via chlorination and phosphorylation steps, resulting in the formation of the desired product. Careful control of temperature and stoichiometry is necessary to achieve high yields and minimize the formation of by-products.

Bis(dichlorophosphoryl)methane finds applications in the synthesis of organophosphorus compounds, particularly those used in agriculture and flame retardancy. Its ability to introduce phosphoryl groups into organic frameworks makes it a valuable reagent for producing pesticides, herbicides, and flame retardants. Additionally, it is used in the preparation of phosphonic acids and related derivatives, which are important in medicinal chemistry and materials science. The compound's reactivity with nucleophiles and its role in the formation of carbon-phosphorus bonds highlight its importance in synthetic chemistry.

Ongoing research aims to expand the scope of bis(dichlorophosphoryl)methane in new synthetic methodologies and explore its potential in developing advanced materials. Its unique combination of functional groups ensures its continued relevance in both academic and industrial settings.


References

2019. Identification of adenine-N9-(methoxy)ethyl-beta-bisphosphonate as NPP1 inhibitor attenuates NPPase activity in human osteoarthritic chondrocytes. Purinergic Signalling, 15(2).
DOI: 10.1007/s11302-019-09649-2

2017. New Synthetic Methods for Phosphate Labeling. Topics in Current Chemistry (Cham), 375(3).
DOI: 10.1007/s41061-017-0135-6

2002. Novel Mycophenolic Adenine Bis(phosphonate) Analogues As Potential Differentiation Agents against Human Leukemia. Journal of Medicinal Chemistry, 45(2).
DOI: 10.1021/jm0104116