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Dibenzo-18-crown-6
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Dibenzo-18-crown-6 98% CAS NO.14187-32-7
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14187-32-7Dibenzo-18-crown-6
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14187-32-7 Usage

Purification Methods

Crystallise it from *benzene, n-heptane or toluene and dry it under vacuum at room temperature for several days. [Szezygiel J Phys Chem 91 1252 1987, V.gtle ed. Top Corr Chem (Host Guest Complex Chemistry) 98 1981.]

Chemical Properties

white to slightly beige fluffy powder
InChI:InChI=1/C20H24O6/c1-3-7-19-17(5-1)24-15-13-22-11-9-21-10-12-23-14-16-25-18-6-2-4-8-20(18)26-19/h1-8H,9-16H2

14187-32-7 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (A13133)  Dibenzo-18-crown-6, 98+%    14187-32-7 5g 163.0CNY Detail
Alfa Aesar (A13133)  Dibenzo-18-crown-6, 98+%    14187-32-7 25g 549.0CNY Detail
Alfa Aesar (A13133)  Dibenzo-18-crown-6, 98+%    14187-32-7 100g 1177.0CNY Detail
Aldrich (158399)  Dibenzo-18-crown-6  98% 14187-32-7 158399-2.5G 321.75CNY Detail
Aldrich (158399)  Dibenzo-18-crown-6  98% 14187-32-7 158399-10G 629.46CNY Detail
Aldrich (158399)  Dibenzo-18-crown-6  98% 14187-32-7 158399-50G 2,155.14CNY Detail
Sigma-Aldrich (49902)  Tin(II)ionophoreI  Selectophore 14187-32-7 49902-50MG-F 234.00CNY Detail

14187-32-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name dibenzo-18-crown-6

1.2 Other means of identification

Product number -
Other names Dibenzo-18-crown 6-Ether

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:14187-32-7 SDS

14187-32-7Synthetic route

benzene-1,2-diol
120-80-9

benzene-1,2-diol

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

3-oxa-1,5-dichloropentane

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide for 0.0833333h; Microwave irradiation;79%
With potassium carbonate In N,N-dimethyl-formamide for 24h; Reflux;21%
Stage #1: benzene-1,2-diol; 3-oxa-1,5-dichloropentane With sodium hydroxide In butan-1-ol at 90℃; for 2h; Heating;
Stage #2: With sodium hydroxide for 16h; Reflux; Inert atmosphere;
3.47%
With potassium carbonate In butan-1-ol at 115℃;
With sodium hydroxide In dimethyl sulfoxide
bis(2-hydroxyphenoxyethyl)ether
23116-94-1

bis(2-hydroxyphenoxyethyl)ether

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

3-oxa-1,5-dichloropentane

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide for 0.0833333h; Microwave irradiation;73%
With potassium carbonate In acetonitrile at 85℃; for 36h;69%
With sodium hydroxide 1.) n-BuOH, MeOH, 2.) n-BuOH, reflux, 17 h; Yield given. Multistep reaction;
benzene-1,2-diol
120-80-9

benzene-1,2-diol

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

3-oxa-1,5-dichloropentane

A

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

B

1,2-bis[2'-(2''-chloroethoxy)ethoxy]benzene
41758-00-3

1,2-bis[2'-(2''-chloroethoxy)ethoxy]benzene

C

2-(5-chloro-3-oxa-1-pentyloxy)phenol
111875-63-9

2-(5-chloro-3-oxa-1-pentyloxy)phenol

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 90℃; for 2.5h; Yields of byproduct given;A 55%
B n/a
C n/a
6,7,9,10,17,18,20,21-Octahydro-5,8,11,16,19,22-hexaoxa-dibenzo[a,j]cyclooctadecene; compound with GENERIC INORGANIC NEUTRAL COMPONENT

6,7,9,10,17,18,20,21-Octahydro-5,8,11,16,19,22-hexaoxa-dibenzo[a,j]cyclooctadecene; compound with GENERIC INORGANIC NEUTRAL COMPONENT

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

Conditions
ConditionsYield
With Iodine monochloride In benzene at 24.9℃; Equilibrium constant;
C20H24O6*C4H10N2*2ClH

C20H24O6*C4H10N2*2ClH

A

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

B

piperazine dihydrochloride
142-64-3

piperazine dihydrochloride

Conditions
ConditionsYield
In water at 25℃; Equilibrium constant;
C20H24O6*C6H12N2*2ClH

C20H24O6*C6H12N2*2ClH

A

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

B

1,4-diaza-bicyclo[2.2.2]octane dihydrochloride
49563-87-3

1,4-diaza-bicyclo[2.2.2]octane dihydrochloride

Conditions
ConditionsYield
In water at 25℃; Equilibrium constant;
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

4,4',5,5'-tetrabromodibenzo-18-crown-6 ether
40100-11-6

4,4',5,5'-tetrabromodibenzo-18-crown-6 ether

Conditions
ConditionsYield
With bromine; acetic acid In water Reflux;100%
With bromine; acetic acid for 5h; Heating;90%
With bromine; acetic acid at 95℃; for 12h; Bromination;80%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

20,25-dinitro-2,3,11,12-dibenzo-1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-diene
32082-46-5

20,25-dinitro-2,3,11,12-dibenzo-1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-diene

Conditions
ConditionsYield
With nitric acid; lanthanum(III) nitrate In acetonitrile at 80℃; for 0.5h; nitrates of oth. metals;100%
With nitric acid; acetic anhydride In chloroform; acetic acid at 50℃; for 5h; Reagent/catalyst; Temperature;
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

2,3,12,13-tetranitro-6,7,9,10,17,18,20,21-octahydro-5,8,11,16,19,22-hexaoxadibenzo[b,k]cyclooctadecene
61853-51-8

2,3,12,13-tetranitro-6,7,9,10,17,18,20,21-octahydro-5,8,11,16,19,22-hexaoxadibenzo[b,k]cyclooctadecene

Conditions
ConditionsYield
With sulfuric acid; nitric acid In dichloromethane at 20℃; for 12h;100%
With nitric acid96%
With sulfuric acid; nitric acid In dichloromethane at 20℃; for 48h;96%
tetrahydrofuran
109-99-9

tetrahydrofuran

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

(borohydrido)(dibenzo-18-crown-6)(tetrahydrofuran)potassium

(borohydrido)(dibenzo-18-crown-6)(tetrahydrofuran)potassium

Conditions
ConditionsYield
With potassium borohydride for 528h; Heating;100%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

1-methoxy-4-(2-nitro-vinyl)-benzene
3179-10-0

1-methoxy-4-(2-nitro-vinyl)-benzene

4',4

4',4"(5")-(dibenzo-18-crown-6)di-4-methoxyphenylacetohydroxamic acid

Conditions
ConditionsYield
With PPA for 1h; Heating;100%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

sodium phenylsulfonate
515-42-4

sodium phenylsulfonate

C20H24O6*C6H5O3S(1-)*Na(1+)

C20H24O6*C6H5O3S(1-)*Na(1+)

Conditions
ConditionsYield
In methanol at 60℃; for 1h;100%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

sodium 3-nitrobenzenesulfonate
127-68-4

sodium 3-nitrobenzenesulfonate

C20H24O6*C6H4NO5S(1-)*Na(1+)

C20H24O6*C6H4NO5S(1-)*Na(1+)

Conditions
ConditionsYield
In methanol at 60℃; for 1h;100%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

sodium tosylate
657-84-1

sodium tosylate

C20H24O6*C7H7O3S(1-)*Na(1+)

C20H24O6*C7H7O3S(1-)*Na(1+)

Conditions
ConditionsYield
In methanol at 60℃; for 1h;100%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

[1,2,5]thiadiazolo[3,4-c][1,2,5]thiadiazole
55904-34-2

[1,2,5]thiadiazolo[3,4-c][1,2,5]thiadiazole

C20H24O6*C2N4S2

C20H24O6*C2N4S2

Conditions
ConditionsYield
In dichloromethane at 20℃;100%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

1-selena-2,5-diaza-2,4-cyclopentadiene-3,4-dicarbonitrile
106013-47-2

1-selena-2,5-diaza-2,4-cyclopentadiene-3,4-dicarbonitrile

C4N4Se*C20H24O6

C4N4Se*C20H24O6

Conditions
ConditionsYield
In dichloromethane at 20℃;100%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

potassium decacyanodicobaltate

potassium decacyanodicobaltate

(dibenzo-18-crown-6)potassium pentacyanocobaltate(II)

(dibenzo-18-crown-6)potassium pentacyanocobaltate(II)

Conditions
ConditionsYield
In methanol Ar-atmosphere; stirring; filtration, evapn. (40°C, crystn. on walls of the vessel);99%
In methanol Ar-atmosphere; stirring; filtration, pptn. on ether addn., filtration, washing (MeOH/ether = 1/2,then ether), drying (vac., 40°C); elem. anal.;87%
tetrahydrofuran
109-99-9

tetrahydrofuran

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

potassium borohydride

potassium borohydride

(borohydrido)(1,4,7,10,13,16-hexaoxa-2,3:11,12-dibenzocyclooctadeca-2,11-diene-κ(6)O)(tetrahydrofuran)potassium
927437-38-5

(borohydrido)(1,4,7,10,13,16-hexaoxa-2,3:11,12-dibenzocyclooctadeca-2,11-diene-κ(6)O)(tetrahydrofuran)potassium

Conditions
ConditionsYield
In tetrahydrofuran an NMR tube charged with KBH4, dibenzo-18-crown-6 and THF, refluxed for 22 d;99%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

potassium tetrakis(allyl)gallate
1356843-06-5

potassium tetrakis(allyl)gallate

[K(dibenzo-18-crown-6)][Ga(η1-allyl)4]
1356843-08-7

[K(dibenzo-18-crown-6)][Ga(η1-allyl)4]

Conditions
ConditionsYield
In tetrahydrofuran under Ar, Schlenk techniques; dibenzocrown in THF added to soln. of Ga compd. in THF; volatiles removed (reduced pressure), pentane added to oil, supernatant decanted, residue washed (pentane), solid dried (vac.); elem. anal., XRD;99%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

[Al(η1-allyl)3(THF)]
1253215-98-3

[Al(η1-allyl)3(THF)]

allyl potassium
60647-46-3, 7329-38-6

allyl potassium

[K(dibenzo-18-crown-6][tetrakis(η1-allyl)aluminate]
1320213-77-1

[K(dibenzo-18-crown-6][tetrakis(η1-allyl)aluminate]

Conditions
ConditionsYield
In tetrahydrofuran under Ar, Schlenk technique; addn. of allylpotassium and dibenzo-18-crown-6 to soln. of Al complex in THF; evapn. under vac., oily residue washed with pentane, solid dried under vac.; elem. anal.;98%
methanol
67-56-1

methanol

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

C20H24O6*CH4O*6HO(1-)*6K(1+)

C20H24O6*CH4O*6HO(1-)*6K(1+)

Conditions
ConditionsYield
With potassium hydroxide at 60℃; for 1h;97.9%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

diphenyliodonium hexafluorophosphate
58109-40-3

diphenyliodonium hexafluorophosphate

diphenyliodonium hexafluorophosphate-dibenzo-18-crown-6 ether complex

diphenyliodonium hexafluorophosphate-dibenzo-18-crown-6 ether complex

Conditions
ConditionsYield
In ethyl acetate for 0.0833333h; Reflux;97.6%
1,3-DIOXOLANE
646-06-0

1,3-DIOXOLANE

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

sodium thiocyanide
540-72-7

sodium thiocyanide

C20H24O6*C3H6O2*CNS(1-)*Na(1+)

C20H24O6*C3H6O2*CNS(1-)*Na(1+)

Conditions
ConditionsYield
for 1h; Ambient temperature;97%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

4',4

4',4"(5")-(dibenzo-18-crown-6)diphenylacetohydroxamic acid

Conditions
ConditionsYield
With PPA for 2h; Heating;97%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

niobium pentachloride

niobium pentachloride

NbCl5(dibenzo-18-crown-6)

NbCl5(dibenzo-18-crown-6)

Conditions
ConditionsYield
In dichloromethane Ar-atmosphere; molar ratio Nb2Cl10:crown=1:2, room temp.; elem. anal.;97%
tetrahydrofuran
109-99-9

tetrahydrofuran

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

[sodium phosphaethynolate•(dioxane)2.5]

[sodium phosphaethynolate•(dioxane)2.5]

[sodium(phosphaethynolate)(dibenzo-18-crown-6)(tetrahydrofuran)]

[sodium(phosphaethynolate)(dibenzo-18-crown-6)(tetrahydrofuran)]

Conditions
ConditionsYield
at 20℃; for 12h; Inert atmosphere;97%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

dichloro(mesitylene)ruthenium(II) dimer

dichloro(mesitylene)ruthenium(II) dimer

nitromethane
75-52-5

nitromethane

silver trifluoromethanesulfonate
2923-28-6

silver trifluoromethanesulfonate

(η6-1,3,5-C6H3Me3)Ru(η6-dibenzo-18-crown-6)(OTf)2

(η6-1,3,5-C6H3Me3)Ru(η6-dibenzo-18-crown-6)(OTf)2

Conditions
ConditionsYield
In nitromethane byproducts: AgCl; (Ar), mixt. of Ru complex and AgOTf (1:4) stirred for 1 h in CH3NO2, AgCl filtered off, treated with 2 equiv. of dibenzo-18-crown-6, refluxed for 8 h; filtered, evapd.(vac.), washed (CH2Cl2), dissolved (acetone), chromy.(Al2O3 - acetone/EtOH 1:1), concd., pptd.(Et2O), elem. anal.;96%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

tert-butyl alcohol
75-65-0

tert-butyl alcohol

4'-tert-Butyldibenzo-18-crown-6
75264-22-1

4'-tert-Butyldibenzo-18-crown-6

Conditions
ConditionsYield
With sulfuric acid; sodium perchlorate In chloroform Heating; or KClO4;95%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

acetic anhydride
108-24-7

acetic anhydride

1,1'-(6,7,9,10,17,18,20,21-octahydrodibenzo[b,k]-[1,4,7,10,13,16]hexaoxacyclooctadecine-2,13-diyl)diethanone
67722-66-1

1,1'-(6,7,9,10,17,18,20,21-octahydrodibenzo[b,k]-[1,4,7,10,13,16]hexaoxacyclooctadecine-2,13-diyl)diethanone

Conditions
ConditionsYield
With phosphoric acid at 60℃; for 4h; Temperature;95%
With acetic acid at 96 - 100℃; for 1h;87%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

tris(pivaloyltrifluoroacetonate)erbium(III) aquate

tris(pivaloyltrifluoroacetonate)erbium(III) aquate

tris(pivaloyltrifluoroacetonate) erbium(III)*dibenzo-18-crown-6

tris(pivaloyltrifluoroacetonate) erbium(III)*dibenzo-18-crown-6

Conditions
ConditionsYield
In neat (no solvent) heated to 100°C; dibenzo-18-crown-6 added with stirring; stirred for 5-10 min;; washed (water); filtered; dried at room temp.; sublimated (vac.); elem. anal.;;95%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

zinc borohydride

zinc borohydride

2Zn(2+)*4(BH4)(1-)*(C6H4O)2(OCH2CH2)4 = (Zn(BH4)2)2*(C6H4O)2(OCH2CH2)4

2Zn(2+)*4(BH4)(1-)*(C6H4O)2(OCH2CH2)4 = (Zn(BH4)2)2*(C6H4O)2(OCH2CH2)4

Conditions
ConditionsYield
In diethyl ether under inert atm.; dibenzo-18-crown-6 added to soln. of Zn(BH4)2 in diethyl ether, stirred for 10 h; filtered off, washed (diethyl ether); elem. anal., DTA;95%
In tetrahydrofuran
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

zinc(II) tetrahydroborate

zinc(II) tetrahydroborate

zinc borohydride dibenzo-18-crown-6 adduct

zinc borohydride dibenzo-18-crown-6 adduct

Conditions
ConditionsYield
In diethyl ether inert atmosphere; crown ether addn. to soln. of B-compd., stirring (10 h); ppt. filtration off, washing (diethyl ether), vacuum drying; elem. anal.;95%
In diethyl ether stirring (room temp., 10 h, pptn.); filtration, washing (ether), drying (vac., room temp., 20 h); elem. anal.;90%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

[((t)Bu3SiO)Cr(μ-OSi(t)Bu3)2]Na * benzene
851625-22-4

[((t)Bu3SiO)Cr(μ-OSi(t)Bu3)2]Na * benzene

[((t)Bu3SiO)3Cr][Na(dibenzo-18-crown-6)]
851625-24-6

[((t)Bu3SiO)3Cr][Na(dibenzo-18-crown-6)]

Conditions
ConditionsYield
In benzene dibenzo-18-crown-6 added to a soln. of Cr complex; crystd. for 12 h; elem. anal.;95%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

4,4'-dibromodibenzo-18-crown-6 ether
110692-06-3

4,4'-dibromodibenzo-18-crown-6 ether

Conditions
ConditionsYield
With N-Bromosuccinimide In chloroform at 20℃;94%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

2,13-Diiodo-6,7,9,10,17,18,20,21-octahydro-5,8,11,16,19,22-hexaoxa-dibenzo[a,j]cyclooctadecene
134403-52-4

2,13-Diiodo-6,7,9,10,17,18,20,21-octahydro-5,8,11,16,19,22-hexaoxa-dibenzo[a,j]cyclooctadecene

Conditions
ConditionsYield
With sulfuric acid; dihydrogen peroxide; iodine In ethanol for 4h; Heating;94%
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

Nd-trispivaloyltrifluoroacetonate*2H2O

Nd-trispivaloyltrifluoroacetonate*2H2O

tris(pivaloyltrifluoroacetonate) neodymium(III)*dibenzo-18-crown-6

tris(pivaloyltrifluoroacetonate) neodymium(III)*dibenzo-18-crown-6

Conditions
ConditionsYield
In chloroform boiled for 1 h;; evapd. in air at room temp.; washed (H2O); filtered; dried; sublimated (vac.); elem. anal.;;94%

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