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Name |
Dibenzo-18-crown-6 |
EINECS | 238-041-3 |
CAS No. | 14187-32-7 | Density | 1.108 g/cm3 |
PSA | 55.38000 | LogP | 2.94880 |
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 | N/A | 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); |
Article Data | 19 |
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 |
bis(2-hydroxyphenoxyethyl)ether
3-oxa-1,5-dichloropentane
dibenzo-18-crown-6
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; |
benzene-1,2-diol
3-oxa-1,5-dichloropentane
A
dibenzo-18-crown-6
B
1,2-bis[2'-(2''-chloroethoxy)ethoxy]benzene
C
2-(5-chloro-3-oxa-1-pentyloxy)phenol
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 |
dibenzo-18-crown-6
Conditions | Yield |
---|---|
With Iodine monochloride In benzene at 24.9℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In water at 25℃; Equilibrium constant; |
A
dibenzo-18-crown-6
B
1,4-diaza-bicyclo[2.2.2]octane dihydrochloride
Conditions | Yield |
---|---|
In water at 25℃; Equilibrium constant; |
dibenzo-18-crown-6
4,4',5,5'-tetrabromodibenzo-18-crown-6 ether
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% |
dibenzo-18-crown-6
20,25-dinitro-2,3,11,12-dibenzo-1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-diene
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; |
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
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% |
tetrahydrofuran
dibenzo-18-crown-6
Conditions | Yield |
---|---|
With potassium borohydride for 528h; Heating; | 100% |
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.
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%.
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. |