tert-Butylphosphonic dichloride
[CAS# 4707-95-3]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: tert-Butylphosphonic dichloride
• Synonyms: 2-dichlorophosphoryl-2-methylpropane
• Molecular Formula: C₄H₉Cl₂OP
• Molecular Weight: 174.99
• CAS Registry Number: 4707-95-3
• EC Number: 623-583-9
• SMILES: CC(C)(C)P(=O)(Cl)Cl

Properties

• Melting point: 121-123 °C

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
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Substances or mixtures corrosive to metals	Met. Corr.	1	H290

• Transport Information: UN 3261

Discovery and Applications

tert-Butylphosphonic dichloride is an important chemical compound in the field of organophosphorus chemistry, known for its distinct reactivity and applications in various chemical processes. This compound, with the molecular formula C4H10Cl2O2P, features a tert-butyl group attached to a phosphonic dichloride moiety, giving it unique properties that are valuable in both synthetic and industrial contexts.

The discovery of tert-Butylphosphonic dichloride arose from efforts to develop new organophosphorus reagents with enhanced reactivity and selectivity. The synthesis of this compound involves the chlorination of tert-butylphosphonic acid or its esters. Typically, this reaction is carried out using a chlorinating agent such as thionyl chloride (SOCl2) under controlled conditions. The resulting product is characterized by its two chlorides and a tert-butyl group, which impart specific chemical properties.

In synthetic chemistry, tert-Butylphosphonic dichloride is utilized as a reagent for the introduction of phosphonic groups into organic molecules. Its application is particularly notable in the formation of phosphonate esters, which are valuable intermediates in the synthesis of various pharmaceuticals and agrochemicals. The reactivity of tert-Butylphosphonic dichloride allows for efficient phosphorylation of alcohols and phenols, facilitating the preparation of diverse phosphonate compounds.

The compound also finds use in the development of ligands for metal-catalyzed reactions. By reacting with other compounds, tert-Butylphosphonic dichloride can form phosphine oxides or phosphine ligands, which are then employed in catalytic processes such as cross-coupling reactions and hydrogenation. The steric and electronic properties of the tert-butyl group contribute to the performance of these catalysts, enhancing their selectivity and efficiency.

In materials science, tert-Butylphosphonic dichloride is used to modify surfaces and create functionalized materials. For instance, it can be employed to introduce phosphonic acid groups onto various substrates, which can improve adhesion and surface properties. This application is valuable in the fabrication of advanced coatings and materials used in electronics and other high-tech industries.

Handling and storage of tert-Butylphosphonic dichloride require standard precautions due to its corrosive and reactive nature. It should be stored in a dry, cool place, away from moisture and air, to maintain its stability and prevent hydrolysis.

Future research on tert-Butylphosphonic dichloride may explore its potential in new synthetic methodologies and applications. Investigations into its reactivity and interactions with other chemical species could lead to further advancements in organophosphorus chemistry and materials science.

References

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