Dibenzo-18-crown-6 supplier | CasNO.14187-32-7

Name
Dibenzo-18-crown-6
EINECS 238-041-3
CAS No. 14187-32-7
Article Data19
CAS DataBase
Density 1.108 g/cm³
Solubility sparingly soluble in water
Melting Point 162-164 °C(lit.)
Formula C₂₀H₂₄O₆
Boiling Point 503.1 °C at 760 mmHg
Molecular Weight 360.407
Flash Point 206 °C
Transport Information
Appearance white to slightly beige fluffy powder
Safety 26-36/37/39
Risk Codes 36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xi,Xn
Synonyms Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecane;NSC 147771;Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin,6,7,9,10,17,18,20,21-octahydro-;Dibenzo-18-crown-6(6,7,9,10,17,18,20,21-Octahydrodibenzo);
PSA 55.38000
LogP 2.94880

Synthetic route

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

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

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

Conditions

Conditions	Yield
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

: 23116-94-1
bis(2-hydroxyphenoxyethyl)ether

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

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

Conditions

Conditions	Yield
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;

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

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

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

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

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

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 90℃; for 2.5h; Yields of byproduct given;	A 55% B n/a C n/a

...Expand

: 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

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

Conditions

Conditions	Yield
With Iodine monochloride In benzene at 24.9℃; Equilibrium constant;

: C20H24O6*C4H10N2*2ClH

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

B: 142-64-3
piperazine dihydrochloride

Conditions

Conditions	Yield
In water at 25℃; Equilibrium constant;

: C20H24O6*C6H12N2*2ClH

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

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

Conditions

Conditions	Yield
In water at 25℃; Equilibrium constant;

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

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

Conditions

Conditions	Yield
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%

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

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

Conditions

Conditions	Yield
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;

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

: 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

Conditions	Yield
With sulfuric acid; nitric acid In dichloromethane at 20℃; for 12h;	100%
With nitric acid	96%
With sulfuric acid; nitric acid In dichloromethane at 20℃; for 48h;	96%

: 109-99-9
tetrahydrofuran

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

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

Conditions

Conditions	Yield
With potassium borohydride for 528h; Heating;	100%

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

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

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

Conditions

Conditions	Yield
With PPA for 1h; Heating;	100%

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

: 515-42-4
sodium phenylsulfonate

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

Conditions

Conditions	Yield
In methanol at 60℃; for 1h;	100%

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

: 127-68-4
sodium 3-nitrobenzenesulfonate

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

Conditions

Conditions	Yield
In methanol at 60℃; for 1h;	100%

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

: 657-84-1
sodium tosylate

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

Conditions

Conditions	Yield
In methanol at 60℃; for 1h;	100%

: 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

Conditions	Yield
In dichloromethane at 20℃;	100%

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

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

: C4N4Se*C20H24O6

Conditions

Conditions	Yield
In dichloromethane at 20℃;	100%

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

: potassium decacyanodicobaltate

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

Conditions

Conditions	Yield
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%

: 109-99-9
tetrahydrofuran

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

: potassium borohydride

: 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

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

...Expand

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

: 1356843-06-5
potassium tetrakis(allyl)gallate

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

Conditions

Conditions	Yield
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%

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

: 1253215-98-3
[Al(η1-allyl)3(THF)]

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

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

Conditions

Conditions	Yield
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%

...Expand

: 67-56-1
methanol

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

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

Conditions

Conditions	Yield
With potassium hydroxide at 60℃; for 1h;	97.9%

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

: 58109-40-3
diphenyliodonium hexafluorophosphate

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

Conditions

Conditions	Yield
In ethyl acetate for 0.0833333h; Reflux;	97.6%

: 646-06-0
1,3-DIOXOLANE

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

: 540-72-7
sodium thiocyanide

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

Conditions

Conditions	Yield
for 1h; Ambient temperature;	97%

...Expand

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

: 102-96-5
(2-nitroethenyl)benzene

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

Conditions

Conditions	Yield
With PPA for 2h; Heating;	97%

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

: niobium pentachloride

: NbCl5(dibenzo-18-crown-6)

Conditions

Conditions	Yield
In dichloromethane Ar-atmosphere; molar ratio Nb2Cl10:crown=1:2, room temp.; elem. anal.;	97%

: 109-99-9
tetrahydrofuran

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

: [sodium phosphaethynolate•(dioxane)2.5]

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

Conditions

Conditions	Yield
at 20℃; for 12h; Inert atmosphere;	97%

...Expand

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

: dichloro(mesitylene)ruthenium(II) dimer

: 75-52-5
nitromethane

: 2923-28-6
silver trifluoromethanesulfonate

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

Conditions

Conditions	Yield
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%

...Expand

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

: 75-65-0
tert-butyl alcohol

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

Conditions

Conditions	Yield
With sulfuric acid; sodium perchlorate In chloroform Heating; or KClO4;	95%

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

: 108-24-7
acetic anhydride

: 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

Conditions	Yield
With phosphoric acid at 60℃; for 4h; Temperature;	95%
With acetic acid at 96 - 100℃; for 1h;	87%

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

: tris(pivaloyltrifluoroacetonate)erbium(III) aquate

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

Conditions

Conditions	Yield
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%

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

: zinc borohydride

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

Conditions

Conditions	Yield
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

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

: zinc(II) tetrahydroborate

: zinc borohydride dibenzo-18-crown-6 adduct

Conditions

Conditions	Yield
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%

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

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

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

Conditions

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

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

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

Conditions

Conditions	Yield
With N-Bromosuccinimide In chloroform at 20℃;	94%

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

: 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

Conditions	Yield
With sulfuric acid; dihydrogen peroxide; iodine In ethanol for 4h; Heating;	94%

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

: Nd-trispivaloyltrifluoroacetonate*2H2O

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

Conditions

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

Dibenzo-18-crown-6 Specification

The Dibenzo-18-crown-6, with the CAS registry number 14187-32-7, is also known as Dibenzo(b,k)(1,4,7,10,13,16)hexaoxacyclooctadecane. It belongs to the product categories of API intermediates; Crown Ethers; Functional Materials; Macrocycles for Host-Guest Chemistry. Its EINECS number is 238-041-3. This chemical's molecular formula is C₂₀H₂₄O₆ and molecular weight is 360.40. What's more, its systematic name is 6,7,9,10,17,18,20,21-octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecine. Its classification codes are: (1)Drug / Therapeutic Agent; (2)Skin / Eye Irritant. It is stable at common pressure and temperature, and it should be sealed and stored in a cool, ventilated and dry place. Moreover, it should be protected from oxides and light. This chemical is a benzannulated crown ether. It is related to the non-benzannulated 18-crown-6. It is used as phase transfer catalyst and coordination reagent.

Physical properties of Dibenzo-18-crown-6 are: (1)ACD/LogP: 1.84; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.84; (4)ACD/LogD (pH 7.4): 1.84; (5)ACD/BCF (pH 5.5): 14.63; (6)ACD/BCF (pH 7.4): 14.63; (7)ACD/KOC (pH 5.5): 237.5; (8)ACD/KOC (pH 7.4): 237.5; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 55.38 Å²; (13)Index of Refraction: 1.5; (14)Molar Refractivity: 95.7 cm³; (15)Molar Volume: 325.1 cm³; (16)Polarizability: 37.94×10^-24cm³; (17)Surface Tension: 39.3 dyne/cm; (18)Density: 1.108 g/cm³; (19)Flash Point: 206 °C; (20)Enthalpy of Vaporization: 74.31 kJ/mol; (21)Boiling Point: 503.1 °C at 760 mmHg; (22)Vapour Pressure: 9.33E-10 mmHg at 25°C.

Preparation: this chemical can be synthesized from catechol and bis(chloroethyl)ether.

Dibenzo-18-crown-6 can be synthesized from catechol and bis(chloroethyl)ether

Uses of Dibenzo-18-crown-6: it can be used to produce cis-4,4'-Dinitrodibenzo-18-krone-6 at the temperature of 80 °C. It will need reagents 63% aq. HNO₃, La(NO₃)₃·6H₂O and solvent acetonitrile with the reaction time of 30 min. The yield is about 100%.

Dibenzo-18-crown-6 can be used to produce cis-4,4'-Dinitrodibenzo-18-krone-6 at the temperature of 80 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: O1c3c(OCCOCCOc2ccccc2OCCOCC1)cccc3
(2)Std. InChI: InChI=1S/C20H24O6/c1-2-6-18-17(5-1)23-13-9-21-11-15-25-19-7-3-4-8-20(19)26-16-12-22-10-14-24-18/h1-8H,9-16H2
(3)Std. InChIKey: YSSSPARMOAYJTE-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	430mg/kg (430mg/kg)		Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(2), Pg. 48, 1987.
mouse	LD50	oral	4500mg/kg (4500mg/kg)	BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 52(11), Pg. 72, 1987.
rabbit	LD50	intraperitoneal	430mg/kg (430mg/kg)		Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(2), Pg. 48, 1987.
rat	LD50	intraperitoneal	560mg/kg (560mg/kg)		Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(2), Pg. 48, 1987.
rat	LD50	oral	2600mg/kg (2600mg/kg)	BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985.

Product Name

Dibenzo-18-crown-6

Synthetic route

Dibenzo-18-crown-6 Specification

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