2-Chloro-1,3,2-dioxaphospholane-2-oxide

Chemical properties

clear colourless liquid

The Uses of 2-Chloro-1,3,2-dioxaphospholane-2-oxide

2-Chloro-1,3,2-dioxaphospholane-2-oxide is used in the synthesis of α-naphthylphosphorylcholine as a method to detect phospholipase C activity.

The Uses of 2-Chloro-1,3,2-dioxaphospholane-2-oxide

Ethylene chlorophosphate is used in the syntheses of 2-methacryloyoxyethylphophocholine, phosphatidylcholines, 2',3'-O-16-hentriacontanyliden-adenosine-5'-phosphocholine and hexadecylphosphocholine. It is also involved the synthesis of alpha-naphthylphosphorylcholine, which is used to detect phospholipase C activity. It is an important reactant for the synthesis of a zwitterionic silane, UV-polymerizable lipids utilizing Chabrier reaction and block copolymers of poly(aliphatic ester) clickable polyphosphoester.

The Uses of 2-Chloro-1,3,2-dioxaphospholane-2-oxide

2-Chloro-1,3,2-dioxaphospholane 2-oxide may be used in the synthesis of:

• 2-methacryloyloxyethylphosphorylcholine
• miltefosine (hexadecylphosphocholine, MT) analogs
• phosphoric acid 2-trimethylamino-ethyl ester undec-10-enyl ester
• uridine nucleolipid, (2′,3′-O-16-hentriacontanyliden-uridine-5′-phosphocholine, PUPC)
• adenosine nucleoamphiphile, (2′,3′-O-16-hentriacontanyliden-adenosine-5′-phosphocholine, PAPC)
• structurally related phospholipids which are either conformationally restricted or flexible
• phosphatidylcholines

General Description

2-Chloro-1,3,2-dioxaphospholane 2-oxide (COP) is a cyclic chlorophosphate reagent that can be prepared from 2-chloro-1,3,2-dioxaphospholane by reacting with molecular oxygen.

Purification Methods

It should be distilled under high vacuum as some polymerisation occurs at -1atmospheric pressure. It has IR bands at 3012, 2933, 1477, 1366, 1325, 1040, 924 and 858 cm . It is hydrolysed to HOCH2CH2OPO3H2 in 30minutes in H2O at 100o [IR: Cox & Westheimer J Am Chem Soc 80 5441 1958]. [Beilstein 1 IV 2419.]