Изопропенилфосфондихлорид

Description

Isopropenylphosphonide chloride - isopropenylphosphonic acid chloride, formula C3H5Cl2OP; combines a reactive phosphonyl dichloride group –P(O)Cl2 and a polymerizable vinyl (isopropenyl) double bond.

The chlorine atoms at the phosphorus atom are easily replaced by nucleophiles (alcohols, amines, water) to form the corresponding phosphonate esters and amides, and the remaining isopropenyl double bond allows the resulting derivatives to further undergo radical polymerization - this is how polymerizable phosphorus-containing monomers are obtained from the acid chloride.

Basic Attributes

• CAS No: 3944-27-2
• Chemical formula: C3H5Cl2OP
• Molecular weight: 158.95
• Exact weight: 157.94600
• HS code: 2931900090
• Specifications PSA: 26.88000
• XLogP3: 3.19070

Physico-chemical characteristics

• Density: 1.326 g/cm3
• Boiling point: 181.3 °C at 760 mm Hg. Art.
• Flash point: 63.4 °C
• Refractive index: 1.447

Scope of application

It is used as an intermediate compound in the synthesis of organophosphorus reagents: by reaction with alcohols and amines, esters and amides of isopropenylphosphonic acid are obtained from it, which are used as polymerizable monomers to impart fire resistance to polymer materials and as building blocks in the fine organic synthesis of phosphorus-containing compounds.

• raw materials for the production of esters and amides of isopropenylphosphonic acid
• intermediate in the synthesis of polymerizable phosphorus-containing monomers
• phosphorylation reagent in fine organic synthesis
• starting material for the development of phosphorus-based flame retardants

Advantages

The presence of two reaction centers in one molecule at once - a hydrolytically labile P(O)Cl2 group and a polymerizable vinyl bond - makes it possible to obtain functional phosphonate monomers in one step without the separate introduction of a polymerizable fragment, which reduces the number of synthesis stages compared to separate phosphorylation and subsequent grafting of a vinyl group.

Storage and transportation conditions

Store in a hermetically sealed container in an inert gas atmosphere, since phosphonic acid chlorides are sensitive to moisture and are hydrolyzed by atmospheric water to release hydrogen chloride. The room is dry, ventilated, away from open flame sources - flash point 63.4 °C.

Delivery form and quality

The density of the substance 1.326 g/cm3 and the refractive index 1.447 are used as parameters to control the purity of the product batch, along with the boiling point of 181.3 °C at 760 mmHg. Art., since phosphonic acid chlorides easily hydrolyze upon contact with air moisture and lose their reactivity. The XLogP3 index of 3.19070 and the polar surface area of ​​PSA 26.88000 are characteristic of phosphonic acid chlorides of medium molecular weight.