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Key Documents

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377953

Sigma-Aldrich

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

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C2H4ClO3P
Numero CAS:
6609-64-9
Peso molecolare:
142.48
Beilstein:
606582
Numero CE:
229-560-6
Numero MDL:
MFCD00043138
Codice UNSPSC:
12352100
ID PubChem:
24863533
NACRES:
NA.22

Forma fisica

liquid

Impurezze

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

Indice di rifrazione

n20/D 1.45 (lit.)

P. eboll.

89-91 °C/0.8 mmHg (lit.)

Punto di fusione

12-14 °C (neat) (lit.)

Densità

1.55 g/mL at 25 °C (lit.)

Temperatura di conservazione

−20°C

Stringa SMILE

ClP1(=O)OCCO1

InChI

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

Descrizione generale

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.

Applicazioni

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

Pittogrammi

Corrosion
GHS05

Avvertenze

Danger

Indicazioni di pericolo

H314

Classi di pericolo

Eye Dam. 1 - Skin Corr. 1B

Rischi supp

EUH014,EUH029

Codice della classe di stoccaggio

8A - Combustible corrosive hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

>235.4 °F - closed cup

Punto d’infiammabilità (°C)

> 113 °C - closed cup

Dispositivi di protezione individuale

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

Certificati d'analisi (COA)

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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
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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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