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

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Synonym(s):
2-Chloro-2-oxo-1,3,2-dioxaphospholane, Ethylene glycol chlorophosphate
Empirical Formula (Hill Notation):
C2H4ClO3P
CAS Number:
Molecular Weight:
142.48
Beilstein/REAXYS Number:
606582
EC Number:
MDL number:
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

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This Item
391220375217541508
vibrant-m

391220

2-Chloro-1,3,2-dioxaphospholane

bp

89-91 °C/0.8 mmHg (lit.)

bp

62 °C/20 mmHg (lit.)

bp

-

bp

-

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

-

storage temp.

-

density

1.55 g/mL at 25 °C (lit.)

density

1.422 g/mL at 25 °C (lit.)

density

-

density

-

mp

12-14 °C (neat) (lit.)

mp

-

mp

71-74 °C (lit.)

mp

97-102 °C (lit.)

refractive index

n20/D 1.45 (lit.)

refractive index

n20/D 1.489 (lit.)

refractive index

-

refractive index

-

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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Synthesis and tensioactive properties of PEO-b-polyphosphate copolymers
Stephanie V et al.
Royal Society of Chemistry Advances, 5, 27330-27337 (2015)
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)
Toward the Efficient Synthesis of New Phosphopantothenate Derivatives by Using Chlorophosphate Reagents.
Pahor J, et al.
Synthesis, 48(21), 3763-3772 (2016)
Phospholipid based polymer as drug release coating for cardiovascular device.
Xu J-P, et al.
Eur. Polymer J., 40(2), 291-298 (2004)
Journal of the American Chemical Society, 115, 6600-6600 (1993)

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