1,4,7,10,13-pentaoxacyclopentadecane

• ChemBase ID: 75097
• Molecular Formular: C10H20O5
• Molecular Mass: 220.2628
• Monoisotopic Mass: 220.13107374
• SMILES: O1CCOCCOCCOCCOCC1
• Canonical SMILES: O1CCOCCOCCOCCOCC1
• InChI: InChI=1S/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2
• InChIKey: VFTFKUDGYRBSAL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4,7,10,13-pentaoxacyclopentadecane
• IUPAC Systematic name: 1,4,7,10,13-Pentaoxacyclopentadecane
• IUPAC Traditional name: 15-crown-5 ether
• Synonyms: 15-Crown-5; Lead ionophore V; 15-Crown-5; 1,4,7,10,13-Pentaoxacyclopentadecane; 1,4,7,10,13-Pentaoxacyclopentadecane; 15-CROWN-5; 1,4,7,10,13-五氧环十五烷; 15-冠醚-5; 15-冠-5; 铅离子载体 V; 15-冠-5醚

Database IDs

• CAS Number: 33100-27-5
• EC Number: 251-379-6
• MDL Number: MFCD00005110
• Beilstein Number: 1618144
• PubChem SID: 24851323; 162040015; 24849297; 24856851
• PubChem CID: 36336
• CHEBI ID: 32401
• CHEMBL: 156289
• Chemspider ID: 33416
• Gmelin ID: 3897
• MeSH Name: 15-Crown-5
• Wikipedia Title: 15-Crown-5

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.23487754
• LogD (pH = 7.4): -0.23487754
• Log P: -0.23487754
• Molar Refractivity: 55.2175 cm^3
• Polarizability: 21.964964 Å^3
• Polar Surface Area: 46.15 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Transparent liquid
• Boiling Point: 116°C (at 240 Pa); 150-155°C; 150-155°C/0.5mm; 93-96 °C/0.05 mmHg(lit.)
• Flash Point: >110°C; >110°C(230°F); 113 °C; 235.4 °F
• Density: 1.109; 1.11 g/ml; 1.110; 1.113 g cm^-3 (at 20 °C); 1.113 g/mL at 20 °C(lit.)
• Refractive Index: 1.4615; 1.465; 1.4650; n20/D 1.465; n20/D 1.465(lit.)
• Partition Coefficient: -0.639
• Std enthalpy of combustion: -5.9157--5.9129 MJ mol^-1
• Std enthalpy of formation: -881.1--877.1 kJ mol^-1

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate
• Storage Warning: Harmful/Irritant/Moisture Sensitive/Hygroscopic/Store under Argon; Hygroscopic
• RTECS: SB0200000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38; 22-36/38; R:22-36; R22, R36/38
• Safety Statements: 23-26-36/37; 26; S:26-36/37/39; S26
• TSCA Listed: 是
• GHS Pictograms: GHS exclamation mark; GHS06; GHS07
• GHS Signal Word: WARNING; Warning
• NFPA704:
  

  1

  2

  0
• GHS Hazard statements: 302, 315, 319; H301-H315-H319-H335; H302-H315-H319
• GHS Precautionary statements: 305+351+338; P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥98.0% (GC); 95+%; 98%
• Grade: purum; Selectophore™
• Empirical Formula (Hill Notation): C10H20O5

DETAILS

MP Biomedicals - 02150730

1 ml = approx. 1.11 g
Solubilizes metal ions in non-polar solvents.
Useful phase transfer catalyst and complexing-agent.

Sigma Aldrich - 188832

Packaging
1, 5, 25 g in glass bottle

Sigma Aldrich - 28123

Other Notes
Phase transfer catalyst, complexing-agent1,2

Sigma Aldrich - 15328

Other Notes
Ionophore with good selectivity and stability for lead1
Legal Information
Selectophore is a trademark of Sigma-Aldrich GmbH

REFERENCES

• Crown ether (see Appendix 2) especially suited to complexing sodium ions. Thus, catalyzes the O-alkylation of the Na salts of carboxylic acids in the penicillin and cephalosporin series, providing a method for esterification without exposure to acid: Synthesis, 52, (1986).
• Greatly facilitates the Williamson synthesis of ethers with hindered alcohols and NaH: Tetrahedron Lett., 38, 4679 (1997). Promotes the cleavage of unsymmetrical ethers by Sodium iodide, A15480, in the opposite sense to BBr₃, i.e. by nucleophilic displacement from the less substituted carbon atom: Tetrahedron Lett., 22, 4239 (1981).
• Greatly increases the reactivity of phosphonate anions generated by reaction with NaH in the Horner-Wadsworth-Emmons reaction. Thus, has been used in a high-yield synthesis of stilbenes from aldehydes and Diethyl benzylphosphonate, A10645: Synthesis, 117 (1981).
• Use in combination with Lithium aluminum hydride, A18116, enables reductions to be carried out in hydrocarbon solvents: J. Chem. Soc., Chem. Commun., 1234 (1985).