1,4,7,10,13,16-hexaoxacyclooctadecane

• ChemBase ID: 75098
• Molecular Formular: C12H24O6
• Molecular Mass: 264.31536
• Monoisotopic Mass: 264.15728849
• SMILES: O1CCOCCOCCOCCOCCOCC1
• Canonical SMILES: O1CCOCCOCCOCCOCCOCC1
• InChI: InChI=1S/C12H24O6/c1-2-14-5-6-16-9-10-18-12-11-17-8-7-15-4-3-13-1/h1-12H2
• InChIKey: XEZNGIUYQVAUSS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4,7,10,13,16-hexaoxacyclooctadecane
• IUPAC Traditional name: 18-crown-6 ether
• Synonyms: 18-Crown-6; 1,4,7,10,13,16-Hexaoxacyclooctadecane 99%; 1,4,7,10,13,16-Hexaoxacyclooctadecane; 18-CROWN-6; 18-Crown-6; 1,4,7,10,13,16-hexaoxacyclooctadecane; 18-Crown-6 ether; Ethylene Oxide Cyclic Hexamer; NSC 159836; 18-冠-6醚; 1,4,7,10,13,16-六氧环十八烷; 18-冠醚-6

Database IDs

• CAS Number: 17455-13-9
• EC Number: 241-473-5
• MDL Number: MFCD00005113
• Beilstein Number: 1619616
• Merck Index: 142602
• PubChem SID: 162040016; 24846099; 24851233; 24856618
• PubChem CID: 28557
• CHEBI ID: 32397
• CHEMBL: 155204
• Chemspider ID: 26563
• Wikipedia Title: 18-Crown-6

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): -0.28185305
• LogD (pH = 7.4): -0.28185305
• Log P: -0.28185305
• Molar Refractivity: 66.261 cm^3
• Polarizability: 26.357956 Å^3
• Polar Surface Area: 55.38 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 37–40 °C; 37-41°C; 37-45°C; 38-41 °C; 40-45°C; 42 - 45°C; 42-45 °C(lit.)
• Boiling Point: 116°C/0.2mm; 116 °C (0.2 Torr); 116°C/0.2mm
• Flash Point: > 110°C; >113 °C; >235.4 °F; 109°C; 109°C(228°F)
• Density: 1.175; 1.237 g/cm3
• Hydrophobicity(logP): -1.182

Safety Information

• Storage Condition: 2-8°C
• Storage Warning: Harmful/Irritant/Hygroscopic/Store under Argon; Hygroscopic
• RTECS: MP4500000
• European Hazard Symbols: Highly toxic (T+); X; Harmful (Xn)
• UN Number: 2810
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: I
• Australian Hazchem: 2XE
• Risk Statements: 22-36; 22-36/37/38; R:22-27
• Safety Statements: 26-36; S:28-29-36/37/39-45
• EU Classification: T1
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 153
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335; H302-H319-H313
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P305+P351+P338-P301+P312-P312-P337+P313-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0%; ≥99.0% (GC); 95%; 95+%; 99%
• Grade: for ion chromatography; purum
• Cation Traces: Al: ≤1 mg/kg; Ba: ≤1 mg/kg; Bi: ≤1 mg/kg; Ca: ≤5 mg/kg; Cd: ≤1 mg/kg; Co: ≤1 mg/kg; Cr: ≤1 mg/kg; Cu: ≤1 mg/kg; Fe: ≤1 mg/kg; K: ≤1 mg/kg; Li: ≤1 mg/kg; Mg: ≤1 mg/kg; Mn: ≤1 mg/kg; Mo: ≤1 mg/kg; Na: ≤20 mg/kg; NH4+: ≤50 mg/kg; Ni: ≤1 mg/kg; Pb: ≤1 mg/kg; Sr: ≤1 mg/kg; Zn: ≤1 mg/kg
• Empirical Formula (Hill Notation): C12H24O6

DETAILS

MP Biomedicals - 02150731

Phase transfer catalyst and complexing-agent.

Sigma Aldrich - C5515

Application
有效用作相转移催化剂。
Other Notes
具有重复 (-CH2CH2O) 单元的大环聚醚。该化合物为离子载体型(与阳离子形成稳定的复合物)。

Sigma Aldrich - 186651

Application
Can be useful as phase-transfer catalysts.
Phase-transfer catalyst used in a chemoselective reduction of fused tetrazoles with NaBH4 and potassium hydroxide.
Other Notes
Macrocyclic polyethers with repeating (-CH2CH2O) units. The compounds are ionophoric (form stable complexes with cations).
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 274984

Application
Can be useful as phase-transfer catalysts.
Complexing agent which solubilizes cations in non-polar solvents.
Other Notes
Macrocyclic polyethers with repeating (-CH2CH2O) units. The compounds are ionophoric (form stable complexes with cations).
Packaging
1 g in glass bottle

Sigma Aldrich - 07673

Application
Can be useful as phase-transfer catalysts.
Other Notes
Macrocyclic polyethers with repeating (-CH2CH2O) units. The compounds are ionophoric (form stable complexes with cations).

Sigma Aldrich - 28125

Application
Can be useful as phase-transfer catalysts.
Other Notes
Macrocyclic polyethers with repeating (-CH2CH2O) units. The compounds are ionophoric (form stable complexes with cations).
Phase transfer catalyst, complexing-agent1,2

Toronto Research Chemicals - C824875

A useful phase transfer catalyst.

REFERENCES

• Crown ether (see Appendix 2) mainly used to complex potassium ions. For a comprehensive study of solvent effects on complexation with K ions in a wide range of solvents, see: J. Org. Chem., 61, 5221 (1996).
• Promotes methylation reactions with Dimethyl carbonate, A13104: Synthesis, 382 (1986). N-Alkylation of Glutarimide, L00968, and Succinimide, A13503: Bull. Soc. Chim. Fr., 227 (1992).
• Enables KH to metallate aryl-substituted methanes directly: J. Am. Chem. Soc., 99, 4457 (1977). In the presence of KOH in DME, various arylmethanes, benzyl alcohols and aldehydes are oxidized to carboxylic acids by molecular oxygen: Tetrahedron Lett., 25, 4989 (1984).
• Has been used with KF to enhance the reactivity of F^- as a base or a nucleophile, e.g. to promote Michael additions in aprotic solvents: J. Chem. Soc., Chem. Commun., 237 (1977), the condensation of nitromethane with aldehydes: Tetrahedron Lett., 3219 (1978), and the transesterification of diaryl to dialkyl phosphonates: Synthesis, 409, 412 (1982).
• Crown ether catalysis can be used in the reaction of KCN with alkyl halides to give nitriles: Tetrahedron Lett., 71 (1975), and for the preparation of acyl cyanides from acid chlorides: Tetrahedron Lett., 21, 2959 (1980). The 1:1 complex between 18-crown-6 and KCN has been used catalytically in the cyanosilylation of aldehydes, ketones and quinones with TMSCN; for examples, see: Org. Synth. Coll., 7, 517 (1990).
• Has been widely used in alkylation reactions with, e.g. K₂CO₃ as base: