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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:
6609-64-9
Molecular Weight:
142.48
Beilstein:
606582
EC Number:
229-560-6
MDL number:
MFCD00043138
UNSPSC Code:
12352100
PubChem Substance ID:
24863533
NACRES:
NA.22

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

Related Categories

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
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Supplementary Hazards

EUH014,EUH029

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG2954
BCCG2953
BCCG2952
BCCG2477
BCBS0995V

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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.
Nanomaterials (Basel, Switzerland), 9(2) (2019-02-16)
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
Louis Moreau et al.
Journal of the American Chemical Society, 130(44), 14454-14455 (2008-10-15)
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)
Chemical permeation enhancers (CPEs) can enable antibiotic flux across the tympanic membrane. Here we study whether combinations of CPEs (sodium dodecyl sulfate, limonene, and bupivacaine hydrochloride) are synergistic and whether they could increase the peak drug flux. Synergy is studied
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