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Cas Database |
| Name |
15-Crown-5 |
EINECS | 251-379-6 |
| CAS No. | 33100-27-5 | Density | 0.995 g/cm3 |
| PSA | 46.15000 | LogP | 0.08300 |
| Solubility | MISCIBLE | Melting Point |
-20oC |
| Formula | C10H20O5 | Boiling Point | 350.9 °C at 760 mmHg |
| Molecular Weight | 220.266 | Flash Point | 139.1 °C |
| Transport Information | N/A | Appearance | colourless liquid |
| Safety | 26-39-36 | Risk Codes | 22-36/38-36-20/22-36/37/38-20/21/22 |
| Molecular Structure |
|
Hazard Symbols |
 Xn, Xi
|
| Synonyms |
5-19-12-00252 (Beilstein Handbook Reference);1,4,10,13-Pentaoxacyclopentadecane;15-crown-5 ether;15-Crown-5(1,4,7,10,13-Pentaoxacyclopentadecane); |
Article Data | 27 |
15-Crown-5 Synthetic route
- 63689-58-7
1,4,7,10,13-pentaoxacyclopentadecane-2,6-dione
- 33100-27-5
15-crown-5
| Conditions | Yield |
|---|---|
| With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1.5h; | 79% |
- 4792-15-8
Pentaethylene glycol
- 33100-27-5
15-crown-5
| Conditions | Yield |
|---|---|
| With sodium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 80℃; | 75% |
| With sodium hydroxide; p-toluenesulfonyl chloride In 1,2-dimethoxyethane at 0℃; Product distribution; var. solvents, reagents, and temp.; other oligoethylene glycols; | 36 % Chromat. |
| Conditions | Yield |
|---|---|
| With sodium carbonate; dicyclohexyl-carbodiimide In 1,4-dioxane at 70 - 75℃; for 6h; Concentration; Reagent/catalyst; Temperature; Solvent; | 70.2% |
- 111-44-4
3-oxa-1,5-dichloropentane
- 112-27-6
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
- 33100-27-5
15-crown-5
| Conditions | Yield |
|---|---|
| With sodium methylate In 1,4-dioxane for 24h; Heating; metal hydroxides, different bases as 'template' agents; | 66% |
| With sodium methylate In 1,4-dioxane for 24h; Heating; | 66% |
- 86309-76-4
1,4,7,10,13-Pentaoxacyclopentadecane-2,3-dithione
- 33100-27-5
15-crown-5
| Conditions | Yield |
|---|---|
| With nickel In diethyl ether; dichloromethane at 0℃; for 1h; | 52% |
- 4792-15-8
Pentaethylene glycol
A
- 33100-27-5
15-crown-5
B
- 71092-63-2
<60>crown-20
C
- 52985-64-5
<30>crown-10
D
- 109635-67-8
45-Crown-15
| Conditions | Yield |
|---|---|
| With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 65℃; | A 46% B 0.7% C 12% D 3.4% |
| Conditions | Yield |
|---|---|
| With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 65℃; | A 46% B 12% C 3.4% |
| Conditions | Yield |
|---|---|
| With potassium hydroxide for 0.133333h; microwave irradiation; | 40% |
- 7460-82-4
diethylene glycol ditosylate
- 112-27-6
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
- 33100-27-5
15-crown-5
| Conditions | Yield |
|---|---|
| With aluminum oxide; potassium fluoride In acetonitrile for 24h; Ambient temperature; | 25% |
| Conditions | Yield |
|---|---|
| In benzene at 25℃; Equilibrium constant; |
15-Crown-5 Chemical Properties
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IUPAC Name: 3,6,9,12,15-Pentaoxacyclopentadecane
Molecular Formula: C10H20O5
Molecular Weight: 220.26 g/mol
Canonical SMILES: C1COCCOCCOCCOCCO1
InChI: InChI=1/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2
EINECS: 251-379-6
Classification Code: Drug / Therapeutic Agent; Skin / Eye Irritant
Product Categories: Crown Ethers; Functional Materials; Macrocycles for Host-Guest Chemistry
Stability: Stable. Incompatible with oxidizing agents, strong acids. Avoid exposure to water or moist air.
Water Solubility: Miscible
Sensitive: Hygroscopic
XLogP3: -0.5
H-Bond Acceptor: 5
Index of Refraction: 1.404
Molar Refractivity: 54.14 cm3
Molar Volume: 221.3 cm3
Polarizability: 21.46×10-24 cm3
Surface Tension: 31.2 dyne/cm
Density: 0.995 g/cm3
Flash Point: 139.1 °C
Enthalpy of Vaporization: 57.2 kJ/mol
Boiling Point: 350.9 °C at 760 mmHg
Water Solubility: 8.82E+04 mg/L at 25 °C
Henry's Law Constant: 2.22E-11 atm-m3/mole at 25 °C
Atmospheric OH Rate Constant: 7.01E-11 cm3/molecule-sec at 25 °C
Vapour Pressure of 15-Crown-5 (CAS NO.33100-27-5): 1.44E-03 mm Hg at 25 °C
15-Crown-5 Uses
15-Crown-5 (CAS NO.33100-27-5) is used as phase transfer catalyst, metal complexing agent, selective removal and separation of cation.
15-Crown-5 Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 514mg/kg (514mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985. |
| mouse | LD50 | oral | 1020mg/kg (1020mg/kg) | BEHAVIORAL: TREMOR | Toxicology and Applied Pharmacology. Vol. 44, Pg. 263, 1978. |
| rabbit | LD50 | intraperitoneal | 560mg/kg (560mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(2), Pg. 48, 1987. | |
| rabbit | LD50 | skin | 2520mg/kg (2520mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985. |
| rat | LD50 | intraperitoneal | 530mg/kg (530mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985. |
| rat | LD50 | oral | 1410mg/kg (1410mg/kg) | BEHAVIORAL: TREMOR | Drug and Chemical Toxicology. Vol. 1, Pg. 339, 1978. |
15-Crown-5 Consensus Reports
Reported in EPA TSCA Inventory.
15-Crown-5 Safety Profile
Moderately toxic by ingestion, skin contact, and intraperitoneal routes. A skin and eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes:
Xn, 
Xi
Risk Statements: 22-36/38-36-20/22-36/37/38-20/21/22
R22: Harmful if swallowed.
R36/38: Irritating to eyes and skin.
R36: Irritating to eyes.
R20/22: Harmful by inhalation and if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-39-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S39: Wear eye / face protection.
S36: Wear suitable protective clothing.
RIDADR: 2810
WGK Germany: 3
Hazard Note: Irritant
HazardClass: 6.1(b)
PackingGroup of 15-Crown-5 (CAS NO.33100-27-5): III
15-Crown-5 Specification
15-Crown-5 (CAS NO.33100-27-5), its Synonyms are 1,4,7,10,13-Pentaoxacyclopentadecane ; 15-Crown-5,1,4,7,10,13-Pentaoxa-cyclo-pentadecane ; Crownethers ; Ethyleneoxidecyclicpentamer ; Lead ionophore V . It is colourless liquid. It is a cyclic pentamer of ethylene oxide that has been shown to complex with various cations, including sodium (Na+) and potassium (K+), but selective binding to lead (Pb2+).
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