18-crown-6 ether
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1.5h; | 92% |
1,4,7,10,13,16-hexaoxacyclooctadecane-2,6-dione
18-crown-6 ether
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1.5h; | 89% |
18-crown-6 ether
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1.5h; | 83% |
18-crown-6 ether
Conditions | Yield |
---|---|
With calcium oxide In water | 80% |
18-crown-6 ether
Conditions | Yield |
---|---|
With calcium oxide In water | 80% |
chloro-trimethyl-silane
A
18-crown-6 ether
B
octakis(i-propyl)cycloterasilane
Conditions | Yield |
---|---|
In benzene Ring cleavage; | A n/a B 9% C 79% |
triethylene glycol di-(p-toluenesulfonate)
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
18-crown-6 ether
Conditions | Yield |
---|---|
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% |
18-crown-6 ether
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1.5h; | 77% |
pentaethylene glycol
18-crown-6 ether
Conditions | Yield |
---|---|
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 60℃; | 75% |
pentaethylene glycol
A
18-crown-6 ether
B
<36>crown-12
C
54-Crown-18
Conditions | Yield |
---|---|
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 65℃; | A 69% B 1.1% C 0.1% |
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
18-crown-6 ether
Conditions | Yield |
---|---|
With p-toluenesulfonyl chloride; potassium hydroxide In tetrahydrofuran at 55 - 60℃; for 3h; | 65.2% |
With sodium hydroxide; benzenesulfonyl chloride In various solvent(s) Ambient temperature; | |
Multi-step reaction with 2 steps 1: 34 percent / toluene 2: 92 percent / LiAlH4 / tetrahydrofuran / 1.5 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: thionyl chloride View Scheme |
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane at 27℃; for 0.5h; | 58% |
With aluminum oxide; potassium fluoride In acetonitrile for 24h; Ambient temperature; | 70 % Chromat. |
Conditions | Yield |
---|---|
With potassium hydroxide In water at 20℃; for 0.333333h; | 55% |
1,2-bis(2-chloroethoxy)ethane
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
18-crown-6 ether
Conditions | Yield |
---|---|
With potassium hydroxide for 0.133333h; microwave irradiation; | 54% |
With potassium hydroxide In tetrahydrofuran at 70℃; for 13h; Inert atmosphere; | 35% |
1,4,7,10,13,16-Hexaoxacyclooctadecane-2,3-dithione
18-crown-6 ether
Conditions | Yield |
---|---|
With nickel In diethyl ether; dichloromethane at 0℃; for 1h; | 45% |
tetraethylene glycol di(p-toluenesulfonate)
diethylene glycol
18-crown-6 ether
Conditions | Yield |
---|---|
With potassium hydroxide In tetrahydrofuran at 20℃; for 1h; | 45% |
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
A
18-crown-6 ether
B
C42H84O21
C
<27>crown-9
D
<36>crown-12
Conditions | Yield |
---|---|
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 65℃; Further byproducts given; | A 42% B 1.3% C 10% D 4.1% |
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
A
18-crown-6 ether
B
<27>crown-9
C
<36>crown-12
D
45-Crown-15
Conditions | Yield |
---|---|
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 65℃; Further byproducts given; | A 42% B 10% C 4.1% D 2.2% |
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
A
18-crown-6 ether
B
<27>crown-9
C
<36>crown-12
D
45-Crown-15
E
54-Crown-18
Conditions | Yield |
---|---|
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 65℃; Product distribution; var. glycols; template effect of K(+).; | A 42% B 10% C 4.1% D 2.2% E 2% |
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
A
18-crown-6 ether
B
<27>crown-9
C
<36>crown-12
D
54-Crown-18
Conditions | Yield |
---|---|
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 65℃; Further byproducts given; | A 42% B 10% C 4.1% D 2% |
triethylene glycol di-(p-toluenesulfonate)
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
A
18-crown-6 ether
B
<36>crown-12
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 25℃; | A 40% B 13% |
Tetraethylene glycol
diethylene glycol ditosylate
A
18-crown-6 ether
B
<36>crown-12
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 25℃; | A 37% B 18% |
Conditions | Yield |
---|---|
With potassium hydroxide In tetrahydrofuran | 34% |
With potassium hydroxide In tetrahydrofuran Heating; | 30% |
With potassium hydroxide In tetrahydrofuran Heating; other metal hydroxides as 'template' agents; | 30% |
With potassium hydroxide In tetrahydrofuran for 18h; Heating; | |
In tetrahydrofuran for 24h; Heating; |
Tetraethylene glycol
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
A
18-crown-6 ether
B
1,4,7,10,13,16,10-heptaoxacyclohenicosane
C
24-crown-8
Conditions | Yield |
---|---|
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 60℃; | A 19% B 33% C 14% |
18-crown-6 ether
Conditions | Yield |
---|---|
With sodium amalgam In benzene Heating; | 25% |
Tetraethylene glycol
diethylene glycol
A
(1,4,7,10-tetraoxacyclododecane)
B
18-crown-6 ether
C
24-crown-8
Conditions | Yield |
---|---|
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 60℃; | A n/a B 23% C 3% |
1,4,7,10,13,16-Hexaoxacyclooctadecane-2,3,11,12-tetrathione
18-crown-6 ether
Conditions | Yield |
---|---|
With nickel In diethyl ether; dichloromethane at 0℃; for 1h; | 21% |
18-crown-6 ether
Conditions | Yield |
---|---|
With sodium amalgam In benzene Heating; | 16% |
15-crown-5
A
18-crown-6 ether
Conditions | Yield |
---|---|
In benzene at 25℃; Equilibrium constant; |
1,4,7,10,13,16,10-heptaoxacyclohenicosane
(18-crown-6)potassium
A
18-crown-6 ether
Conditions | Yield |
---|---|
In gas at 76.9℃; Equilibrium constant; Thermodynamic data; ΔG; |
18-crown-6 ether
Conditions | Yield |
---|---|
With dinitrogen tetroxide; Nitrogen dioxide In dichloromethane at -10℃; for 0.5h; | 100% |
With dinitrogen tetraoxide; Nitrogen dioxide In dichloromethane at -10℃; for 0.5h; | 100% |
With dinitrogen tetraoxide In chloroform at -10℃; for 1h; complexation; | 90% |
18-crown-6 ether
iodosylbenzene
Conditions | Yield |
---|---|
With tetrafluoroboric acid dimethyl ether complex In dichloromethane at -78 - 0℃; for 3.5h; | 100% |
18-crown-6 ether
Conditions | Yield |
---|---|
In toluene for 24h; | 100% |
18-crown-6 ether
antimonypentachloride
Conditions | Yield |
---|---|
In acetonitrile PbCl2 is dissolved by injection of SbCl5 in MeCN, addn. of 18-crown-6; concn. the volume under vac., standing for some time at 20°C, filtn., elem. anal.; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran; water slow addn. of concd. acid to THF soln of 18-crown-6, pptn.; filtered, washed (diethyl ether), dried in air, elem. anal.; | 100% |
18-crown-6 ether
B
hydrogen
Conditions | Yield |
---|---|
In tetrahydrofuran byproducts: BEt3; molar ratio NB10H13:KBHEt3 1:2, cooling (-78°C), stirring (2 h, room temp.); evapn. (vac.), dissoln. (THF), crystn. (-40°C), recrystn. (CH3CN); elem. anal.; | A 23% B 100% |
18-crown-6 ether
[W(carbonyl)5([bis(trimethylsilyl)methyl]cyanophosphane)]
potassium tert-butylate
[(OC)5WP(CH(SiMe3)2)CNK(18-crown-6)]
Conditions | Yield |
---|---|
In tetrahydrofuran under Ar; cooled (-80°C) soln. of KO-t-Bu in THF added dropwise to stirred soln. of W complex in THF and 18-crown-6; warmed slowly to room temp. for 3.5 h; solvent removed under vac.; washed with Et2O and n-pentane; dried under reduced pressure; elem. anal.; | 100% |
methanol
18-crown-6 ether
1,3,5-tris(2,6-dimethyl-4-hydroxyphenyl)benzene
CH4O*C12H24O6*C30H30O3*H2O
Conditions | Yield |
---|---|
With water In ethanol | 100% |
18-crown-6 ether
ethanol
1,3,5-tris(4-hydroxyphenyl)mesitylene
benzene
C2H6O*C6H6*C12H24O6*C27H24O3*H2O
Conditions | Yield |
---|---|
With water | 100% |
(hydrido)(5,10,15,20-tetrakis(p-tolyl)porphyrinato)iridium(III)
18-crown-6 ether
potassium (18-crown-6)(5,10,15,20-tetrakis(p-tolyl)porphyrinato)iridate(I)
Conditions | Yield |
---|---|
With potassium hydroxide In tetrahydrofuran at 150℃; for 0.75h; | 100% |
18-crown-6 ether
Conditions | Yield |
---|---|
With potassium phosphate In water at 20℃; for 12h; | 100% |
18-crown-6 ether
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate In water at 20℃; for 12h; | 100% |
18-crown-6 ether
Conditions | Yield |
---|---|
With potassium dihydrogenphosphate In water at 20℃; for 12h; | 100% |
18-crown-6 ether
Conditions | Yield |
---|---|
With potassium bromide In water at 20℃; for 12h; | 100% |
18-crown-6 ether
Conditions | Yield |
---|---|
With potassium nitrate In water at 20℃; for 12h; | 100% |
18-crown-6 ether
Conditions | Yield |
---|---|
With potassium hydroxide In water at 20℃; for 12h; | 100% |
18-crown-6 ether
Conditions | Yield |
---|---|
With potassium chlorate In water at 20℃; for 12h; | 100% |
18-crown-6 ether
Conditions | Yield |
---|---|
With potassium bromate In water at 20℃; for 12h; | 100% |
Conditions | Yield |
---|---|
In water at 20℃; for 12h; | 100% |
Conditions | Yield |
---|---|
In water at 20℃; for 12h; | 100% |
Conditions | Yield |
---|---|
In water at 20℃; for 12h; | 100% |
Conditions | Yield |
---|---|
With potassium hydroxide In tetrahydrofuran at 150℃; for 0.75h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
In toluene (N2) Hf complex, K and 18-crown-6 in toluene were stirred for 24 h; pentane was added, ppt. was filtered off; elem. anal.; | 100% |
Conditions | Yield |
---|---|
Inert atmosphere; Schlenk technique; | 100% |
Conditions | Yield |
---|---|
Inert atmosphere; Schlenk technique; | 100% |
Conditions | Yield |
---|---|
In dichloromethane at -78 - 0℃; for 3.5h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
In dichloromethane at -78 - 0℃; for 4h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With potassium superoxide In dimethyl sulfoxide at 25℃; for 0.25h; | 100% |
aluminum (III) chloride
18-crown-6 ether
Conditions | Yield |
---|---|
Stage #1: 18-crown-6 ether; potassium chloride In water at 20℃; for 12h; Stage #2: aluminum (III) chloride In ethanol for 12h; Reflux; | 100% |
Conditions | Yield |
---|---|
Stage #1: 18-crown-6 ether; potassium chloride In water at 20℃; for 12h; Stage #2: zinc(II) chloride In ethanol for 12h; Reflux; | 100% |
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 cm3
Molar Volume: 265.5 cm3
Polarizability: 25.75×10-24 cm3
Surface Tension: 31.2 dyne/cm
Density: 0.995 g/cm3
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
18-Crown-6 (CAS NO.17455-13-9) is used as a metal ion complexing agent.
18-Crown-6 (CAS NO.17455-13-9) is commonly producted by the method of Wei Lianlin synthesis.
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, |
Reported in EPA TSCA Inventory.
Hazard Codes: Xn,Xi
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
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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