2-chloro-1,3,2λ5-dioxaphospholan-2-one

• ChemBase ID: 150614
• Molecular Formular: C2H4ClO3P
• Molecular Mass: 142.478121
• Monoisotopic Mass: 141.9586583
• SMILES: C1COP(=O)(O1)Cl
• Canonical SMILES: ClP1(=O)OCCO1
• InChI: InChI=1S/C2H4ClO3P/c3-7(4)5-1-2-6-7/h1-2H2
• InChIKey: SBMUNILHNJLMBF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-chloro-1,3,2λ^5-dioxaphospholan-2-one
• IUPAC Traditional name: 2-chloro-1,3,2λ^5-dioxaphospholan-2-one
• Synonyms: 2-Chloro-2-oxo-1,3,2-dioxaphospholane; Ethylene glycol chlorophosphate; 2-Chloro-1,3,2-dioxaphospholane 2-oxide; 2-Chloro-1,3,2-dioxaphospholane-2-oxide; Ethylene cycl-chlorophosphate; 2-Chloro-2-oxo-1,3,2-dioxaphospholane; 2-Chloro-1,3,2-dioxaphospholane 2-oxide; Ethylene chlorophosphate; 2-氯-2-氧-1,3,2-二氧磷杂环戊烷; 环氯磷酸乙烯酯; 2-氯-1,3,2-二氧磷杂环戊烷 2-氧化物; 2-氯-1,3,2-二氧磷杂环戊烷-2-氧化物; 2-氯-2-氧-1,3,2-二氧磷杂环戊烷; 环氯磷酸乙烯酯

Database IDs

• CAS Number: 6609-64-9
• EC Number: 229-560-6
• MDL Number: MFCD00043138
• Beilstein Number: 606582
• PubChem SID: 24863533; 162244775; 24855591
• PubChem CID: 81087

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.329689
• LogD (pH = 7.4): 0.329689
• Log P: 0.329689
• Molar Refractivity: 25.2192 cm^3
• Polarizability: 10.584635 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 12-14 °C; 12-14 °C (neat)(lit.); 12-14°C
• Boiling Point: 89-91 °C/0.8 mmHg(lit.); 98-99°C/2mm
• Flash Point: >110°C(230°F); >113 °C; >235.4 °F; 113 °C; 235 °F
• Density: 1.55 g/mL at 20 °C(lit.); 1.55 g/mL at 25 °C(lit.); 1.56
• Refractive Index: 1.4500; n20/D 1.448; n20/D 1.449; n20/D 1.45(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3265; UN3265
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 14-34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3265 8/PG 2
• Supplemental Hazard Statements: Reacts violently with water.
• Storage Temperature: -20°C

Product Information

• Purity: ~85% (NMR); ≥95.0% (NMR); 95%
• Grade: purum; technical
• Impurities: <10% 2-Chloro-1,3,2-dioxaphospholane
• Empirical Formula (Hill Notation): C2H4ClO3P

DETAILS

Sigma Aldrich - 377953

Packaging
1, 5 g in glass bottle
Application
Phosphorylating agent used in the syntheses of phosphatidylcholines.1,2
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

Sigma Aldrich - 25748

Other Notes
Reagent used with trimethylamine to transform alcohols into phosphorylcholines1,2,3