Product Name

  • Name

    18-Crown-6

  • EINECS 241-473-5
  • CAS No. 17455-13-9
  • Article Data59
  • CAS DataBase
  • Density 0.995 g/cm3
  • Solubility soluble in water
  • Melting Point 42-45 ºC(lit.)
  • Formula C12H24O6
  • Boiling Point 395.8 ºC at 760 mmHg
  • Molecular Weight 264.319
  • Flash Point 163.8 ºC
  • Transport Information
  • Appearance slightly yellow solid
  • Safety 26-36-39
  • Risk Codes 22-36/37/38-36-20/22-20/21/22
  • Molecular Structure Molecular Structure of 17455-13-9 (18-Crown-6)
  • Hazard Symbols HarmfulXn,IrritantXi
  • Synonyms 18-Crownether-6;18-Crown-6 ether;Ethylene oxide cyclic hexamer;NSC159836;1,4,7,10,13,16-Hexaoxacyclooctadecane;
  • PSA 55.38000
  • LogP 0.09960

Synthetic route

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

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

18-crown-6 ether
17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1.5h;92%
1,4,7,10,13,16-hexaoxacyclooctadecane-2,6-dione
62796-84-3

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

18-crown-6 ether
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

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

18-crown-6 ether
17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1.5h;83%
C12H24O6*C3H7N*ClH

C12H24O6*C3H7N*ClH

18-crown-6 ether
17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
With calcium oxide In water80%
C12H24O6*C7H9N*BrH

C12H24O6*C7H9N*BrH

18-crown-6 ether
17455-13-9

18-crown-6 ether

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

chloro-trimethyl-silane

1,4-dipotassio tetrasilane

1,4-dipotassio tetrasilane

A

18-crown-6 ether
17455-13-9

18-crown-6 ether

B

octakis(i-propyl)cycloterasilane
79848-13-8

octakis(i-propyl)cycloterasilane

C

linear hexasilane

linear hexasilane

Conditions
ConditionsYield
In benzene Ring cleavage;A n/a
B 9%
C 79%
triethylene glycol di-(p-toluenesulfonate)
19249-03-7

triethylene glycol di-(p-toluenesulfonate)

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

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

18-crown-6 ether
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

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

18-crown-6 ether
17455-13-9

18-crown-6 ether

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

pentaethylene glycol

18-crown-6 ether
17455-13-9

18-crown-6 ether

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

pentaethylene glycol

A

18-crown-6 ether
17455-13-9

18-crown-6 ether

B

<36>crown-12
71092-59-6

<36>crown-12

C

54-Crown-18
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%
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

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

18-crown-6 ether
17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
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
Tetraethylene glycol
112-60-7

Tetraethylene glycol

diethylene glycol ditosylate
7460-82-4

diethylene glycol ditosylate

18-crown-6 ether
17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
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.
Pentaethylene glycol
4792-15-8

Pentaethylene glycol

1,2-bis-tosyloxyethane
6315-52-2

1,2-bis-tosyloxyethane

18-crown-6 ether
17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
With potassium hydroxide In water at 20℃; for 0.333333h;55%
1,2-bis(2-chloroethoxy)ethane
112-26-5

1,2-bis(2-chloroethoxy)ethane

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

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

18-crown-6 ether
17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
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
86309-77-5

1,4,7,10,13,16-Hexaoxacyclooctadecane-2,3-dithione

18-crown-6 ether
17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
With nickel In diethyl ether; dichloromethane at 0℃; for 1h;45%
tetraethylene glycol di(p-toluenesulfonate)
37860-51-8

tetraethylene glycol di(p-toluenesulfonate)

diethylene glycol
111-46-6

diethylene glycol

18-crown-6 ether
17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran at 20℃; for 1h;45%
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

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

A

18-crown-6 ether
17455-13-9

18-crown-6 ether

B

C42H84O21
122861-55-6

C42H84O21

C

<27>crown-9
52902-52-0

<27>crown-9

D

<36>crown-12
71092-59-6

<36>crown-12

Conditions
ConditionsYield
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
112-27-6

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

A

18-crown-6 ether
17455-13-9

18-crown-6 ether

B

<27>crown-9
52902-52-0

<27>crown-9

C

<36>crown-12
71092-59-6

<36>crown-12

D

45-Crown-15
109635-67-8

45-Crown-15

Conditions
ConditionsYield
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
112-27-6

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

A

18-crown-6 ether
17455-13-9

18-crown-6 ether

B

<27>crown-9
52902-52-0

<27>crown-9

C

<36>crown-12
71092-59-6

<36>crown-12

D

45-Crown-15
109635-67-8

45-Crown-15

E

54-Crown-18
71092-62-1

54-Crown-18

Conditions
ConditionsYield
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
112-27-6

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

A

18-crown-6 ether
17455-13-9

18-crown-6 ether

B

<27>crown-9
52902-52-0

<27>crown-9

C

<36>crown-12
71092-59-6

<36>crown-12

D

54-Crown-18
71092-62-1

54-Crown-18

Conditions
ConditionsYield
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)
19249-03-7

triethylene glycol di-(p-toluenesulfonate)

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

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

A

18-crown-6 ether
17455-13-9

18-crown-6 ether

B

<36>crown-12
71092-59-6

<36>crown-12

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 25℃;A 40%
B 13%
Tetraethylene glycol
112-60-7

Tetraethylene glycol

diethylene glycol ditosylate
7460-82-4

diethylene glycol ditosylate

A

18-crown-6 ether
17455-13-9

18-crown-6 ether

B

<36>crown-12
71092-59-6

<36>crown-12

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 25℃;A 37%
B 18%
Tetraethylene glycol
112-60-7

Tetraethylene glycol

3-oxa-1,5-dichloropentane
111-44-4

3-oxa-1,5-dichloropentane

18-crown-6 ether
17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran34%
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
112-60-7

Tetraethylene glycol

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

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

A

18-crown-6 ether
17455-13-9

18-crown-6 ether

B

1,4,7,10,13,16,10-heptaoxacyclohenicosane
33089-36-0

1,4,7,10,13,16,10-heptaoxacyclohenicosane

C

24-crown-8
33089-37-1

24-crown-8

Conditions
ConditionsYield
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 60℃;A 19%
B 33%
C 14%
(18-phenylsulfonyl-2,5,8,11,14,17-hexaoxaoctadecylsulfonyl)benzene

(18-phenylsulfonyl-2,5,8,11,14,17-hexaoxaoctadecylsulfonyl)benzene

18-crown-6 ether
17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
With sodium amalgam In benzene Heating;25%
Tetraethylene glycol
112-60-7

Tetraethylene glycol

diethylene glycol
111-46-6

diethylene glycol

A

(1,4,7,10-tetraoxacyclododecane)
294-93-9

(1,4,7,10-tetraoxacyclododecane)

B

18-crown-6 ether
17455-13-9

18-crown-6 ether

C

24-crown-8
33089-37-1

24-crown-8

Conditions
ConditionsYield
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
86309-78-6

1,4,7,10,13,16-Hexaoxacyclooctadecane-2,3,11,12-tetrathione

18-crown-6 ether
17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
With nickel In diethyl ether; dichloromethane at 0℃; for 1h;21%
(9-phenylsulfonyl-2,5,8-trioxanonylsulfonyl)benzene

(9-phenylsulfonyl-2,5,8-trioxanonylsulfonyl)benzene

18-crown-6 ether
17455-13-9

18-crown-6 ether

Conditions
ConditionsYield
With sodium amalgam In benzene Heating;16%
15-crown-5
33100-27-5

15-crown-5

C14H14Mg*C12H24O6

C14H14Mg*C12H24O6

A

18-crown-6 ether
17455-13-9

18-crown-6 ether

B

C14H14Mg*C10H20O5

C14H14Mg*C10H20O5

Conditions
ConditionsYield
In benzene at 25℃; Equilibrium constant;
1,4,7,10,13,16,10-heptaoxacyclohenicosane
33089-36-0

1,4,7,10,13,16,10-heptaoxacyclohenicosane

(18-crown-6)potassium
31270-13-0

(18-crown-6)potassium

A

18-crown-6 ether
17455-13-9

18-crown-6 ether

B

C14H28O7*K(1+)

C14H28O7*K(1+)

Conditions
ConditionsYield
In gas at 76.9℃; Equilibrium constant; Thermodynamic data; ΔG;
18-crown-6 ether
17455-13-9

18-crown-6 ether

[NO+*crown*H(NO3)2-]

[NO+*crown*H(NO3)2-]

Conditions
ConditionsYield
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
17455-13-9

18-crown-6 ether

iodosylbenzene
536-80-1

iodosylbenzene

phenyl(hydroxy)(tetrafluoroborato)-λ3-iodane 18-crown-6 complex (1:1)

phenyl(hydroxy)(tetrafluoroborato)-λ3-iodane 18-crown-6 complex (1:1)

Conditions
ConditionsYield
With tetrafluoroboric acid dimethyl ether complex In dichloromethane at -78 - 0℃; for 3.5h;100%
18-crown-6 ether
17455-13-9

18-crown-6 ether

potassium (5-trifluoroborate-3-tert-butyl-2-trimethylsilanyloxybenzylidene)-(2,6-diisopropylphenyl)amine

potassium (5-trifluoroborate-3-tert-butyl-2-trimethylsilanyloxybenzylidene)-(2,6-diisopropylphenyl)amine

C23H30BF3NO(1-)*C12H24O6*K(1+)

C23H30BF3NO(1-)*C12H24O6*K(1+)

Conditions
ConditionsYield
In toluene for 24h;100%
18-crown-6 ether
17455-13-9

18-crown-6 ether

antimonypentachloride
7647-18-9

antimonypentachloride

lead(II) chloride

lead(II) chloride

{Pb(O6(CH2)12)(CH3CN)3}(2+)*2(SbCl6)(1-)={Pb(O6(CH2)12)(CH3CN)3}{SbCl6}2

{Pb(O6(CH2)12)(CH3CN)3}(2+)*2(SbCl6)(1-)={Pb(O6(CH2)12)(CH3CN)3}{SbCl6}2

Conditions
ConditionsYield
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%
18-crown-6 ether
17455-13-9

18-crown-6 ether

hexafluorotitanic acid

hexafluorotitanic acid

H2TiF6*6H2O*2(C12H24O6)

H2TiF6*6H2O*2(C12H24O6)

Conditions
ConditionsYield
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
17455-13-9

18-crown-6 ether

nido-NB10H13

nido-NB10H13

potassium triethylborohydride

potassium triethylborohydride

A

bis[(18-crown-6)potassium][undecahydro-7-aza-nido-undecaborate]

bis[(18-crown-6)potassium][undecahydro-7-aza-nido-undecaborate]

B

hydrogen
1333-74-0

hydrogen

Conditions
ConditionsYield
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
17455-13-9

18-crown-6 ether

[W(carbonyl)5([bis(trimethylsilyl)methyl]cyanophosphane)]
851576-85-7

[W(carbonyl)5([bis(trimethylsilyl)methyl]cyanophosphane)]

potassium tert-butylate
865-47-4

potassium tert-butylate

[(OC)5WP(CH(SiMe3)2)CNK(18-crown-6)]
947333-63-3

[(OC)5WP(CH(SiMe3)2)CNK(18-crown-6)]

Conditions
ConditionsYield
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
67-56-1

methanol

18-crown-6 ether
17455-13-9

18-crown-6 ether

1,3,5-tris(2,6-dimethyl-4-hydroxyphenyl)benzene
1033846-72-8

1,3,5-tris(2,6-dimethyl-4-hydroxyphenyl)benzene

CH4O*C12H24O6*C30H30O3*H2O
1253939-59-1

CH4O*C12H24O6*C30H30O3*H2O

Conditions
ConditionsYield
With water In ethanol100%
18-crown-6 ether
17455-13-9

18-crown-6 ether

ethanol
64-17-5

ethanol

1,3,5-tris(4-hydroxyphenyl)mesitylene
1253939-64-8

1,3,5-tris(4-hydroxyphenyl)mesitylene

benzene
71-43-2

benzene

C2H6O*C6H6*C12H24O6*C27H24O3*H2O
1253939-66-0

C2H6O*C6H6*C12H24O6*C27H24O3*H2O

Conditions
ConditionsYield
With water100%
(hydrido)(5,10,15,20-tetrakis(p-tolyl)porphyrinato)iridium(III)
105139-33-1

(hydrido)(5,10,15,20-tetrakis(p-tolyl)porphyrinato)iridium(III)

18-crown-6 ether
17455-13-9

18-crown-6 ether

potassium (18-crown-6)(5,10,15,20-tetrakis(p-tolyl)porphyrinato)iridate(I)
1215770-26-5

potassium (18-crown-6)(5,10,15,20-tetrakis(p-tolyl)porphyrinato)iridate(I)

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran at 150℃; for 0.75h;100%
18-crown-6 ether
17455-13-9

18-crown-6 ether

3C12H24KO6*O4P(3-)

3C12H24KO6*O4P(3-)

Conditions
ConditionsYield
With potassium phosphate In water at 20℃; for 12h;100%
18-crown-6 ether
17455-13-9

18-crown-6 ether

2C12H24KO6*HO4P(2-)

2C12H24KO6*HO4P(2-)

Conditions
ConditionsYield
With dipotassium hydrogenphosphate In water at 20℃; for 12h;100%
18-crown-6 ether
17455-13-9

18-crown-6 ether

C12H24KO6*H2O4P(1-)

C12H24KO6*H2O4P(1-)

Conditions
ConditionsYield
With potassium dihydrogenphosphate In water at 20℃; for 12h;100%
18-crown-6 ether
17455-13-9

18-crown-6 ether

Br(1-)*C12H24KO6

Br(1-)*C12H24KO6

Conditions
ConditionsYield
With potassium bromide In water at 20℃; for 12h;100%
18-crown-6 ether
17455-13-9

18-crown-6 ether

C12H24KO6*NO3(1-)

C12H24KO6*NO3(1-)

Conditions
ConditionsYield
With potassium nitrate In water at 20℃; for 12h;100%
18-crown-6 ether
17455-13-9

18-crown-6 ether

C12H24KO6*HO(1-)

C12H24KO6*HO(1-)

Conditions
ConditionsYield
With potassium hydroxide In water at 20℃; for 12h;100%
18-crown-6 ether
17455-13-9

18-crown-6 ether

C12H24KO6*ClO3(1-)

C12H24KO6*ClO3(1-)

Conditions
ConditionsYield
With potassium chlorate In water at 20℃; for 12h;100%
18-crown-6 ether
17455-13-9

18-crown-6 ether

BrO3(1-)*C12H24KO6

BrO3(1-)*C12H24KO6

Conditions
ConditionsYield
With potassium bromate In water at 20℃; for 12h;100%
18-crown-6 ether
17455-13-9

18-crown-6 ether

potassium acetate
127-08-2

potassium acetate

C2H3O2(1-)*C12H24KO6

C2H3O2(1-)*C12H24KO6

Conditions
ConditionsYield
In water at 20℃; for 12h;100%
18-crown-6 ether
17455-13-9

18-crown-6 ether

potassium carbonate
584-08-7

potassium carbonate

CO3(2-)*2C12H24KO6

CO3(2-)*2C12H24KO6

Conditions
ConditionsYield
In water at 20℃; for 12h;100%
18-crown-6 ether
17455-13-9

18-crown-6 ether

potassium hydrogencarbonate
298-14-6

potassium hydrogencarbonate

CHO3(1-)*C12H24KO6

CHO3(1-)*C12H24KO6

Conditions
ConditionsYield
In water at 20℃; for 12h;100%
18-crown-6 ether
17455-13-9

18-crown-6 ether

Ir(ttp)H
105139-33-1

Ir(ttp)H

C12H30KO6(1+)*C48H36IrN4(1-)

C12H30KO6(1+)*C48H36IrN4(1-)

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran at 150℃; for 0.75h; Inert atmosphere;100%
bis(cyclopentadienyl)hafnium dichloride
12116-66-4

bis(cyclopentadienyl)hafnium dichloride

18-crown-6 ether
17455-13-9

18-crown-6 ether

potassium
7440-09-7

potassium

(18-crown-6)*K[Cp2HfCl2]

(18-crown-6)*K[Cp2HfCl2]

Conditions
ConditionsYield
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%
fluorobenzene
462-06-6

fluorobenzene

18-crown-6 ether
17455-13-9

18-crown-6 ether

C16AlF36O4(1-)*Ga(1+)
1402068-67-0

C16AlF36O4(1-)*Ga(1+)

C16AlF36O4(1-)*Ga(1+)*2.25C6H5F*C12H24O6

C16AlF36O4(1-)*Ga(1+)*2.25C6H5F*C12H24O6

Conditions
ConditionsYield
Inert atmosphere; Schlenk technique;100%
fluorobenzene
462-06-6

fluorobenzene

18-crown-6 ether
17455-13-9

18-crown-6 ether

C16AlF36O4(1-)*In(1+)
1262800-74-7

C16AlF36O4(1-)*In(1+)

C16AlF36O4(1-)*In(1+)*2.25C6H5F*C12H24O6

C16AlF36O4(1-)*In(1+)*2.25C6H5F*C12H24O6

Conditions
ConditionsYield
Inert atmosphere; Schlenk technique;100%
tetrafluoroboric acid diethyl ether
67969-82-8

tetrafluoroboric acid diethyl ether

18-crown-6 ether
17455-13-9

18-crown-6 ether

iodosylbenzene
536-80-1

iodosylbenzene

C6H6BF4IO*C12H24O6

C6H6BF4IO*C12H24O6

Conditions
ConditionsYield
In dichloromethane at -78 - 0℃; for 3.5h; Inert atmosphere;100%
18-crown-6 ether
17455-13-9

18-crown-6 ether

iodosylbenzene
536-80-1

iodosylbenzene

boron trifluoride diethyl etherate
109-63-7

boron trifluoride diethyl etherate

C6H6BF4IO*C12H24O6

C6H6BF4IO*C12H24O6

Conditions
ConditionsYield
In dichloromethane at -78 - 0℃; for 4h; Inert atmosphere;100%
18-crown-6 ether
17455-13-9

18-crown-6 ether

C55H10F25S5

C55H10F25S5

C55H10F25S5(1+)*C12H24KO6(1+)

C55H10F25S5(1+)*C12H24KO6(1+)

Conditions
ConditionsYield
With potassium superoxide In dimethyl sulfoxide at 25℃; for 0.25h;100%
aluminum (III) chloride
7446-70-0, 7784-13-6

aluminum (III) chloride

18-crown-6 ether
17455-13-9

18-crown-6 ether

potassium chloride

potassium chloride

C12H24KO6(1+)*AlCl4(1-)

C12H24KO6(1+)*AlCl4(1-)

Conditions
ConditionsYield
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%
18-crown-6 ether
17455-13-9

18-crown-6 ether

potassium chloride

potassium chloride

zinc(II) chloride
7646-85-7

zinc(II) chloride

C12H24KO6(1+)*Cl3Zn(1-)

C12H24KO6(1+)*Cl3Zn(1-)

Conditions
ConditionsYield
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%

18-Crown-6 Chemical Properties


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

18-Crown-6 Uses

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

18-Crown-6 Production

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

18-Crown-6 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,

18-Crown-6 Consensus Reports

Reported in EPA TSCA Inventory.

18-Crown-6 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

18-Crown-6 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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