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377953

Sigma-Aldrich

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

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:
Molecular Weight:
142.48
Beilstein:
606582
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

form

liquid

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

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

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Supplementary Hazards

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

>235.4 °F - closed cup

Flash Point(C)

> 113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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