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33100-27-5

Basic Information
CAS No.: 33100-27-5
Name: 15-Crown-5
Article Data: 27
Molecular Structure:
Molecular Structure of 33100-27-5 (15-Crown-5)
Formula: C10H20O5
Molecular Weight: 220.266
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);
EINECS: 251-379-6
Density: 0.995 g/cm3
Melting Point: -20oC
Boiling Point: 350.9 °C at 760 mmHg
Flash Point: 139.1 °C
Solubility: MISCIBLE
Appearance: colourless liquid
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 22-36/38-36-20/22-36/37/38-20/21/22
Safety: 26-39-36
PSA: 46.15000
LogP: 0.08300
Synthetic route
63689-58-7

1,4,7,10,13-pentaoxacyclopentadecane-2,6-dione

33100-27-5

15-crown-5

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1.5h;79%
4792-15-8

Pentaethylene glycol

33100-27-5

15-crown-5

Conditions
ConditionsYield
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.
112-60-7

Tetraethylene glycol

107-21-1

ethylene glycol

33100-27-5

15-crown-5

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 65℃;A 46%
B 0.7%
C 12%
D 3.4%
4792-15-8

Pentaethylene glycol

A

33100-27-5

15-crown-5

B

52985-64-5

<30>crown-10

C

109635-67-8

45-Crown-15

Conditions
ConditionsYield
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 65℃;A 46%
B 12%
C 3.4%
112-26-5

1,2-bis(2-chloroethoxy)ethane

111-46-6

diethylene glycol

33100-27-5

15-crown-5

Conditions
ConditionsYield
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
ConditionsYield
With aluminum oxide; potassium fluoride In acetonitrile for 24h; Ambient temperature;25%
17455-13-9

18-crown-6 ether

C14H14Mg*C10H20O5

A

33100-27-5

15-crown-5

B

C14H14Mg*C12H24O6

Conditions
ConditionsYield
In benzene at 25℃; Equilibrium constant;
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Chemistry


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

Uses

 15-Crown-5 (CAS NO.33100-27-5) is used as phase transfer catalyst, metal complexing agent, selective removal and separation of cation.

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.

Consensus Reports

Reported in EPA TSCA Inventory.

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:HarmfulXn, IrritantXi 
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

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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