377953

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

• Synonym(s): 2-Chloro-2-oxo-1,3,2-dioxaphospholane, Ethylene glycol chlorophosphate
• 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

Properties

• 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

Description

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

Safety Information

• Pictograms: GHS05
• Signal Word: Danger
• Hazard Statements: H314
• Precautionary Statements: P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363 - P405
• 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