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17455-13-9

Basic Information
CAS No.: 17455-13-9
Name: 18-Crown-6
Article Data: 59
Molecular Structure:
Molecular Structure of 17455-13-9 (18-Crown-6)
Formula: C12H24O6
Molecular Weight: 264.319
Synonyms: 18-Crownether-6;18-Crown-6 ether;Ethylene oxide cyclic hexamer;NSC159836;1,4,7,10,13,16-Hexaoxacyclooctadecane;
EINECS: 241-473-5
Density: 0.995 g/cm3
Melting Point: 42-45 ºC(lit.)
Boiling Point: 395.8 ºC at 760 mmHg
Flash Point: 163.8 ºC
Solubility: soluble in water
Appearance: slightly yellow solid
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 22-36/37/38-36-20/22-20/21/22
Safety: 26-36-39
PSA: 55.38000
LogP: 0.09960
Synthetic route

1,4,7,10,13,16-Hexaoxa-cyclooctadecane-2,9-dione

17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1.5h;92%
62796-84-3

1,4,7,10,13,16-hexaoxacyclooctadecane-2,6-dione

17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1.5h;89%

1,4,7,10,13,16-Hexaoxa-cyclooctadecane-2,12-dione

17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1.5h;83%

C12H24O6*C3H7N*ClH

17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
With calcium oxide In water80%

C12H24O6*C7H9N*BrH

17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
With calcium oxide In water80%
75-77-4

chloro-trimethyl-silane

1,4-dipotassio tetrasilane

A

17455-13-9

18-crown-6 ether

B

79848-13-8

octakis(i-propyl)cycloterasilane

C

linear hexasilane

Conditions
ConditionsYield
In benzene Ring cleavage;A n/a
B 9%
C 79%
19249-03-7

triethylene glycol di-(p-toluenesulfonate)

112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
With aluminum oxide; potassium fluoride In acetonitrile for 72h; Ambient temperature;78%
With potassium hydroxide In water at 25℃; for 0.5h; Solvent; Temperature;54%

1,4,7,10,13,16-Hexaoxa-cyclooctadecane-2,15-dione

17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1.5h;77%
2615-15-8

pentaethylene glycol

17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 60℃;75%
2615-15-8

pentaethylene glycol

A

17455-13-9

18-crown-6 ether

B

71092-59-6

<36>crown-12

C

71092-62-1

54-Crown-18

Conditions
ConditionsYield
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 65℃;A 69%
B 1.1%
C 0.1%
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Chemistry


IUPAC Name: 3,6,9,12,15,18-Hexaoxacyclooctadecane
Molecular Formula: C12H24O6
Molecular Weight: 264.32 g/mol
SMILES: C1COCCOCCOCCOCCOCCO1
InChI: InChI=1/C12H24O6/c1-2-14-5-6-16-9-10-18-12-11-17-8-7-15-4-3-13-1/h1-12H2
EINECS: 241-473-5
Classification Code: Drug / Therapeutic Agent; Skin / Eye Irritant
Product Categories: API intermediates; Crown Ethers; Functional Materials; Macrocycles for Host-Guest Chemistry
storage temperature: Store at 0-5 °C
Water Solubility: SOLUBLE
Sensitive: Hygroscopic
Stability: Stable. Incompatible with strong acids, strong oxidizing agents.
Melting Point: 42-45 °C(lit.)
Index of Refraction: 1.404 
Molar Refractivity: 64.97 cm
Molar Volume: 265.5 cm3 
Polarizability: 25.75×10-24 cm3 
Surface Tension: 31.2 dyne/cm 
Density: 0.995 g/cm
Flash Point: 163.8 °C 
Enthalpy of Vaporization: 62.08 kJ/mol 
Boiling Point: 395.8 °C at 760 mmHg 
Vapour Pressure of 18-Crown-6 (CAS NO.17455-13-9): 4.09E-06 mmHg at 25 °C

Uses

 18-Crown-6 (CAS NO.17455-13-9) is used as a metal ion complexing agent.

Production

 18-Crown-6 (CAS NO.17455-13-9) is commonly producted by the method of Wei Lianlin synthesis.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 59mg/kg (59mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(10), Pg. 92, 1988.
mouse LD50 intraperitoneal 464mg/kg (464mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985.
mouse LD50 intravenous > 1gm/kg (1000mg/kg)   Russian Pharmacology and Toxicology Vol. 47, Pg. 167, 1984.
mouse LD50 oral 540mg/kg (540mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(10), Pg. 92, 1988.
rabbit LD50 skin 3888mg/kg (3888mg/kg) BEHAVIORAL: TREMOR

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
National Technical Information Service. Vol. OTS0571014,
rat LD50 intraperitoneal 830mg/kg (830mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985.
rat LD50 intratracheal 56mg/kg (56mg/kg) BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)"

LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI
National Technical Information Service. Vol. OTS0536187,
rat LD50 oral 525mg/kg (525mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(10), Pg. 92, 1988.
rat LDLo skin 7gm/kg (7000mg/kg)   National Technical Information Service. Vol. OTS0540542,

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes: HarmfulXn,IrritantXi
Risk Statements: 22-36/37/38-36-20/22-20/21/22 
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R36:Irritating to eyes. 
R20/22:Harmful by inhalation and if swallowed. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36-39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S39:Wear eye / face protection.
RIDADR: 2811
WGK Germany: 3
RTECS: MP4500000
F: 10
HazardClass: 6.1(b)
PackingGroup of 18-Crown-6 (CAS NO.17455-13-9): III

Specification

  18-Crown-6 (CAS NO.17455-13-9), its Synonyms are 1,4,7,10,13,16-Hexanoxacyclooctadecane ; 1,4,7,10,13,16-Hexaoxacyclooctadecane ; Ethylene oxide cyclic hexamer . It is slightly yellow solid.

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