1,4,7,10,13,16-Hexaoxacycloocta-decan

18-Crown-6

HCID 28557CAS 17455-13-9
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Grundinformationen

Standard-SMILES
C1COCCOCCOCCOCCOCCO1
InChIKey
XEZNGIUYQVAUSS-UHFFFAOYSA-N
Summenformel
C12H24O6
Durchschnittliche Molmasse
264,31 g/mol
Monoisotopische Masse
264,15728849

Überblick

18-crown-6 is a crown ether that is cyclooctadecane in which the carbon atoms at positions 1, 4, 7, 10, 13 and 16 have been replaced by oxygen atoms. It has a role as a phase-transfer catalyst. It is a saturated organic heteromonocyclic parent and a crown ether.

Namen und Bezeichner

Bevorzugter Name
18-Crown-6
IUPAC
1,4,7,10,13,16-hexaoxacyclooctadecane
Lokaler Name
1,4,7,10,13,16-Hexaoxacycloocta-decan
Englischer Name
18-Crown-6
Summenformel
C12H24O6
Molmasse
264.32

Namen und Synonyme

18-Crown-617455-13-91,4,7,10,13,16-HEXAOXACYCLOOCTADECANEEthylene oxide cyclic hexamerCHEBI:3239763J177NC5BNSC-159836DTXSID7058626RefChem:79335DTXCID5032313241-473-518-crown-6-ether
Weitere Namen anzeigen
18-c-68-Crown-6HEXAOXACYCLOOCTADECANE18-Crown ether-6NSC 15983618-Crown-6 99%
18-Crown-6 ether18-Crown 6-EtherMFCD0000511318-crown61,4,7,10,13,16-Hexaoxacyclooctadecane (18-Crown-6)CHEMBL155204CCRIS 3587EINECS 241-473-5

Datenbank-Bezeichner

CAS
17455-13-9
PubChem CID
28557
DTXSID
DTXSID7058626
ChEMBL
CHEMBL155204
ChEBI
CHEBI:32397
UNII
63J177NC5B
EC Number
241-473-5
Nikkaji
J49.431C

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-0,7
Polarare Oberfläche (TPSA)
55,4 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
0
Schwere Atome
18

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Other Classes -> Other Organic Compounds

Industrial compound

SpringerMaterials PropertiesChemical shift
LogP-0.68
Vapor Pressure0.0000667 [mmHg]
Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical DescriptionClear, odorless, hygroscopic liquid soluble in water and most organic solvents; [Ullmann] White crystals; [MSDSonline]

Physikochemische Eigenschaften

Schmelzpunkt
42 · 42-45 °C(lit.)
Siedepunkt
116 °C · 116°C 0,2mm
Dichte
1 · 1,175 g/cm3
Brechungsindex
1.458 · 1.4580 (estimate)
Flammpunkt
230 °F · >230 °F
storage temp.
30 °C · Store below +30°C.

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (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.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Chemical: 1,4,7,10,13,16-Hexaoxacyclooctadecane

Crown ether 18-crown-6: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 Eintrag

If absorbed, can cause electrolyte imbalance affecting the CNS; Signs of intoxication include hyperventilation, tremor, incoordination, and CNS depression; May damage the skin and eyes; LD50 (mouse) by ingestion is 0.7 g/kg; LD50 (rabbit) by skin absorption is 200 mg/kg; [Ullmann] Toxic by ingestion; A skin, eye, and respiratory tract irritant; Oral LD50 (rat) = 525 mg/kg; Dermal LDLo (rat) = 7000 mg/kg; High-dose feeding causes seizures, weight loss, and liver injury in experimental animals; [MSDSonline]

Hazard Classes and CategoriesAcute Tox. 4 (98.7%)

Toxikologische Informationen

Adverse EffectsNeurotoxin - Other CNS neurotoxin

Sicherheitsdaten

F
10
wgk
3
tsca
TSCA listed
ridadr
2811
hs_code
29329995
RTECS-Nr.
MP4500000

Chemie und Industrie

Verwendung und Herstellung

UsesDrug/ Therapeutic Agent; [ChemIDplus] Used as complexing agents with ammonium ions and metal ions (alkali and alkaline-earth metals); Used as catalysts to make organic chemicals; [Ullmann]
General Manufacturing Information1,4,7,10,13,16-Hexaoxacyclooctadecane: ACTIVE
Anwendungen · 1 Eintrag

Verwenden18-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).

Vor- und nachgelagerte Produkte

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