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377953

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

Name: 2-Chloro-1,3,2-dioxaphospholane 2-oxide
Brand: ALDRICH

Synonym(s):

2-Chloro-2-oxo-1,3,2-dioxaphospholane, Ethylene glycol chlorophosphate

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About This Item

Empirical Formula (Hill Notation):

C₂H₄ClO₃P

CAS Number:

6609-64-9

Molecular Weight:

142.48

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

24863533

EC Number:

229-560-6

Beilstein/REAXYS Number:

606582

MDL number:

MFCD00043138

Form:

liquid

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Properties

form

liquid

Quality Level

200

impurities

<10% 2-Chloro-1,3,2-dioxaphospholane

refractive index

n20/D 1.45 (lit.)

bp

89-91 °C/0.8 mmHg (lit.)

mp

12-14 °C (neat) (lit.)

density

1.55 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

ClP1(=O)OCCO1

InChI

1S/C2H4ClO3P/c3-7(4)5-1-2-6-7/h1-2H2

InChI key

SBMUNILHNJLMBF-UHFFFAOYSA-N

Description

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 .

2-Chloro-1,3,2-dioxaphospholane 2-oxide is used in esterification reactions for cyclic phosphate synthesis, also reacts with phenyl grignard reagents.

Application

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

Reactant for:

Synthesis of amino-functionalized hybrid hydrocarbon/fluorocarbon double-chain phospholipid
Synthesis of UV-polymerizable lipids via Chabrier reaction
Syntheses of block copolymers of poly(aliphatic ester) with clickable polyphosphoester
Imprinting molecular recognition sites on multiwalled carbon nanotubes surface for electrochemical detection of insulin in real samples
Synthesis of a zwitterionic silane
Synthesis of a core-shell-corona micelle stabilized by reversible cross-linkage for intracellular drug delivery