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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/REAXYS Number:
606582
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

form

liquid

Quality Level

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

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

supp_hazards

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

>235.4 °F - closed cup

flash_point_c

> 113 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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Toward the Efficient Synthesis of New Phosphopantothenate Derivatives by Using Chlorophosphate Reagents.
Pahor J, et al.
Synthesis, 48(21), 3763-3772 (2016)
Biomimetic honeycomb-structured surfaces formed from block copolymers incorporating acryloyl phosphorylcholine.
Stenzel MH and Davis TP.
Australian Journal of Chemistry, 56(10), 1035-1038 (2003)
Xue Jiang et al.
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An efficient strategy for growing thermo-sensitive polymers from the surface of exfoliated graphene oxide (GO) is reported in this article. GO sheets with hydroxyls and epoxy groups on the surface were first prepared by modified Hummer's method. Epoxy groups on
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Supramolecular assembly formation resulting from molecular recognition between complementary nucleolipids has been visualized in real time at the micrometer scale.
Rong Yang et al.
Journal of controlled release : official journal of the Controlled Release Society, 289, 94-101 (2018-06-23)
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