18-Crown-6
1,4,7,10,13,16-HEXAOXACYCLOOCTADECANE · 18-c-6 · 8-Crown-6 · HEXAOXACYCLOOCTADECANE · 18-CROWN 6-ETHER · 18-Crown ether-6 · Ethylene oxide cyclic hexamer · 18-CROWN-6
Identifiers & Physical Properties
| CAS No. | 17455-13-9 |
|---|---|
| Molecular formula | C12H24O6 |
| Average molar mass | 264.31 g/mol |
| Monoisotopic mass | 264.15728849 g/mol |
| SMILES | C1COCCOCCOCCOCCOCCO1 |
| InChIKey | XEZNGIUYQVAUSS-UHFFFAOYSA-N |
| PubChem CID | 28557 |
| ChEMBL | CHEMBL155204 |
| ChEBI | CHEBI:32397 |
| EC No. | 241-473-5 |
| DTXSID | DTXSID7058626 |
Chemical & Physical Properties
| XLogP | -0.7 |
|---|---|
| Topological polar surface area | 55.4 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 6 |
| Rotatable bonds | 0 |
| Heavy atoms | 18 |
| Formal charge | 0 |
| Complexity | 108 |
| Chemical classes | Other Classes -> Other Organic CompoundsIndustrial compound |
| SpringerMaterials Properties | Chemical shift |
| LogP (partition coefficient) | -0.68 |
| Vapor pressure | 0.0000667 [mmHg] |
| Food Contact Substances | FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR |
| Physical Description | Clear, odorless, hygroscopic liquid soluble in water and most organic solvents[Ullmann] White crystals[MSDSonline] |
| Melting point | 42-45 °C(lit.) |
| Boiling point | 116°C 0,2mm |
| Density | 1,175 g/cm3 |
| Refractive index | 1.4580 (estimate) |
| Flash point | >230 °F |
| Storage conditions | Store below +30°C. |
| Solubility | Chloroform (Slightly), Methanol (Very Slightly)SOLUBLE |
| Physical state | Crystals or Crystalline Mass or Liquid |
| Color | White or clear colorless |
| Sensitivity | Hygroscopic |
| Merck | 14,2602 |
| BRN | 1619616 |
| Stability | Stable. Incompatible with strong acids, strong oxidizing agents. |
| 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 |
| SMILES | O1CCOCCOCCOCCOCCOCC1 |
| Indirect Additives used in Food Contact Substances | 1,4,7,10,13,16-HEXAOXACYCLOOCTADECANE |
| FDA 21 CFR | 177.2400 |
| CAS DataBase Reference | 17455-13-9(CAS DataBase Reference) |
| FDA UNII | 63J177NC5B |
| NIST Chemistry Reference | 1,4,7,10,13,16-Hexaoxacyclooctadecane(17455-13-9) |
| EPA Substance Registry System | 1,4,7,10,13,16-Hexaoxacyclooctadecane (17455-13-9) |
| UNSPSC Code | 12352005 |
| NACRES | NB.21 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302 |
| GHS precautionary statements | P264-P270-P301+P312-P501 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xn,Xi |
| Risk statements (R) | 22-36/37/38-36-20/22-20/21/22 |
| Safety statements (S) | 26-36-39 |
| UN transport number | 2811 |
| Water hazard class (WGK) | 3 |
| RTECS number | MP4500000 |
| F | 10 |
| TSCA inventory status | TSCA listed |
| Hazard class | 6.1(b)Acute Tox. 4 Oral |
| Packing group | III |
| Customs code | 29329995 |
| Storage class | 11 - Combustible Solids |
| Toxicity | LD50 orally in Rabbit: 525 mg/kg LD50 dermal Rabbit 3888 mg/kg |
Safety & Regulations
| GHS classification | WarningH302 (98.7%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 314 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: 1,4,7,10,13,16-HexaoxacyclooctadecaneCrown ether 18-crown-6: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | If absorbed, can cause electrolyte imbalance affecting the CNSSigns of intoxication include hyperventilation, tremor, incoordination, and CNS depressionMay damage the skin and eyesLD50 (mouse) by ingestion is 0.7 g/kgLD50 (rabbit) by skin absorption is 200 mg/kg[Ullmann] Toxic by ingestionA skin, eye, and respiratory tract irritantOral LD50 (rat) = 525 mg/kgDermal LDLo (rat) = 7000 mg/kgHigh-dose feeding causes seizures, weight loss, and liver injury in experimental animals[MSDSonline] |
| Hazard Classes and Categories | Acute Tox. 4 (98.7%) |
| Adverse effects | Neurotoxin - Other CNS neurotoxin |
| F | 10 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | MP4500000 |
| UN transport number | 2811 |
| Customs code | 29329995 |
| Toxicity | LD50 orally in Rabbit: 525 mg/kg LD50 dermal Rabbit 3888 mg/kg |
| Risk statements (R) | 22-36/37/38-36-20/22-20/21/22 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xn,Xi |
| Safety statements (S) | 26-36-39 |
| Hazard class | 6.1(b)Acute Tox. 4 Oral |
| Storage class | 11 - Combustible Solids |
| Packing group | III |
| GHS hazard statements | H302 |
| GHS precautionary statements | P264-P270-P301+P312-P501 |
Applications & Uses
Uses
18-Crown-6 may be used to catalyze the N-alkylation of heterocyclic compounds and allylation of functionalized aldehydes.
Uses
A useful phase transfer catalyst.
Uses
18-Crown-6 is used as an efficient phase transfer catalyst and as a complexing agent with a variety of small cation. It is involved in the synthesis of diaryl ethers, diaryl thioethers, and diarylamines mediated by potassium fluoride-alumina and 18-crown-6. It facilitates the solubility of potassium permanganate in benzene, which is used for oxidizing the organic compounds. It is used to accelerate various substitution reactions as well as enhances the power of nucleophiles such as potassium acetate. It is utilized in the alkylation reactions in the presence of potassium carbonate, N-alkylation of glutarimide and succinimide with dimethylcarbonate. The complex formed by its reaction with potassium cyanide acts as a catalyst in the cyanosilylation of aldehydes, ketones and quinines with trimethylsilyl cyanide (TMSCN).
General Description
18-Crown-6 is the simplest crown ether that can be prepared by reacting triethylene glycol with triethylene glycol dichloride in the presence of potassium hydroxide as a base. 18-Crown-6 can solubilize metal salts, particularly potassium salts, in nonpolar and dipolar aprotic solvents. Thus, it is widely used as a phase transfer catalyst. It can also be used as a metal complexing agent to prepare a variety of molecular complexes.