DIBENZO-18-CROWN-6
Dibenzo-18-crown-6
CAS: 14187-32-7
Molecular Formula: C20H24O6
DIBENZO-18-CROWN-6 - Names and Identifiers
| Name | Dibenzo-18-crown-6 |
| Synonyms | Dibenzocrown Di-benzo 18-C-6 DIBENZO-18-CROWN-6 Dibenzo-18-crown-6 Dibenzocrownminwhitepowder Dibenzanthracene-18-Crown-6 Diphenyl-18-crown-6-polyether dibenzo[bk][1,4,7,10,13,16]hexaoxacyclooctadecane 2,3,11,12-Dibenzo-1,4,7,10,13,16-hexaoxacyclooctadeca-2,11-diene dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin,6,7,9,10,17,18,20,21-octahyd 6,7,9,10,12,13,20,21-Octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclo-octadecin 6,7,9,10,12,13,15,16-octahydrodibenzo[b,e][1,4,7,10,13,16]hexaoxacyclooctadecine k](1,4,7,10,13,16)hexaoxacyclooctadecin,6,7,9,10,17,18,20,21-octahydro-Dibenzo[b 6,7,9,10,17,18,20,21-octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecine |
| CAS | 14187-32-7 |
| EINECS | 238-041-3 |
| 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 |
| InChIKey | YSSSPARMOAYJTE-UHFFFAOYSA-N |
DIBENZO-18-CROWN-6 - Physico-chemical Properties
| Molecular Formula | C20H24O6 |
| Molar Mass | 360.4 |
| Density | 1.1801 (rough estimate) |
| Melting Point | 162-164 °C (lit.) |
| Boling Point | 380-384 °C (679 mmHg) |
| Flash Point | 380-384°C/679mm |
| Water Solubility | sparingly soluble |
| Solubility | Soluble in CHCl3: 25 mg/ml. |
| Vapor Presure | 3.65E-10mmHg at 25°C |
| Appearance | White to beige powder |
| Color | White to slightly beige |
| Maximum wavelength(λmax) | ['277nm(CH2Cl2)(lit.)'] |
| Merck | 14,2602 |
| BRN | 1162153 |
| Storage Condition | Store below +30°C. |
| Sensitive | air sensitive |
| Refractive Index | 1.5200 (estimate) |
| MDL | MFCD00005098 |
| Physical and Chemical Properties |
|
| Use | For metal ion complexing agents |
DIBENZO-18-CROWN-6 - Risk and Safety
| Risk Codes | R36 - Irritating to the eyes R36/37/38 - Irritating to eyes, respiratory system and skin. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37/39 - Wear suitable gloves and eye/face protection S36 - Wear suitable protective clothing. |
| WGK Germany | 2 |
| RTECS | HP5386000 |
| TSCA | Yes |
| HS Code | 29329995 |
| Hazard Note | Irritant |
| Toxicity | LD50 orally in Rabbit: 2600 mg/kg |
DIBENZO-18-CROWN-6 - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Overview | Dibenzo -18-crown ether -6 is the synthetic raw material of diaminodibenzo -18-crown ether -6, diaminodibenzo -18-crown ether -6 is an important crown ether compound and an important intermediate raw material for the synthesis of crown ether derivatives. The synthesis method is dibenzo -18-crown ether -6 as the raw material, it is prepared by nitration and reduction reaction. The reduction method used is Pd/C reduction method, which is limited due to the high price of the catalyst. The traditional synthesis method of dibenzo -18-crown ether -6, the raw material for synthesizing diaminodibenzo -18-crown ether -6, is reflux reaction under nitrogen protection, with harsh conditions, cumbersome steps, long reaction cycle, high temperature and low yield. Ultrasonic synthesis is a new synthesis method developed in recent years. It has the advantages of good directivity, large energy, and strong penetration ability. It is more convenient and easy to operate than traditional organic synthesis methods. The experimental equipment is also relatively simple and easy to control. It is more and more widely used in organic synthesis. |
| preparation | preparation of dibenzo -18-crown ether -6: weigh a certain amount of catechol, bis-dichloroethyl ether, KOH, a certain volume of DMSO and a small amount of 2,6-di-tert-butyl p-cresol, seal, put into ultrasonic reaction, heat to 50-60 ℃, heat for 3 hours, add water to filter out the black viscous substance while it is hot, wash the filter cake with water and alkali, let the filtrate gradually precipitate off-white solid, filter by suction, and recrystallize with methanol to obtain 2.53g of product with 35.1% yield. |
| Use | Used as metal ion complexing agent Phase transfer catalyst for mono-azaporphyrin synthesis. It is used for ion transmembrane migration 2 and as a reagent for the preparation of synthons for liquid crystal polyesters. |
| production method | note that 1 crown ether is toxic and should be operated carefully. 330 grams (3.00 moles) of o-phenol and 2 liters of n-butanol were added to a 5-liter three-neck flask equipped with a thermometer, a constant pressure drop funnel, a mechanical stirrer and a reflux condenser with an air duct. Under stirring and nitrogen passage, 122g 3.05 mol) granular sodium hydroxide was added. Quickly heat to reflux (about 116 ℃), add 222f g (1.55 mol) bis (2 monochloroethyl) ether and 150 ml n-butanol dropwise for 2 hours. Continue to stir and reflux for 1 cubit, cool to 90 ℃, add 122g (3.05 mol) of granular sodium hydroxide, stir and reflux for 30 minutes, add 222g (1.55 mol) of bis (2-chloroethyl tomb) ether and 150 ml of n-butanol solution for 2 hours. After continuing the reaction for 1 hour, add 21 ml of concentrated hydrochloric acid dropwise to acidify it. After steaming out about 00 ml of n-butanol, add water dropwise to the distillation bottle at a speed that keeps the volume of the mixture in the bottle unchanged. Continue distillation until the temperature of the distillation vapor exceeds 96°C. Cold to 30-40 ℃, dilute the remaining slurry with 500 ml of acetone, stir the condensed sediment, and suck and filter. The crude product is stirred with 2 liters of water, then sucked and filtered, then stirred with 1 liter of acetone, then sucked and filtered, washed with 500 ml of acetone, sucked and dried to obtain 221-260g (39-48%) white fibrous volt crystal, which can be further purified and recrystallized from benzene to obtain white fibrous crystal, |
Last Update：2024-04-11 20:29:24
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