4',4''(5'')-Di-tert-butyldibenzo-18-crown-6
- CAS NO.：29471-17-8
- Empirical Formula: C28H40O6
- Molecular Weight: 472.61
- MDL number: MFCD00068541
- SAFETY DATA SHEET (SDS)
- Update Date: 2025-01-27 09:38:02
What is 4',4''(5'')-Di-tert-butyldibenzo-18-crown-6?
Description
4′,4″(5″)-Di-tert-butyldibenzo-18-crown-6 is a hydrophobic crown ether compound. This crown ether is potentially useful in studies of ion transport through non-polar regions and membranes, and has been described in the design of microsensor devices for ammonia determination based upon ammonia-mediated deprotonation of a pH indicator followed by sequestering of ammonium within the 4′,4″(5″)-Di-tert-butyldibenzo-18-crown-6 sphere.
Chemical properties
Off-white powder
The Uses of 4',4''(5'')-Di-tert-butyldibenzo-18-crown-6
4'',4''''(5'''')-Di-tert-butyldibenzo-18-crown-6 is a hydrophobic crown ether compound..
What are the applications of Application
4′,4′′(5′′)-Di-tert-butyldibenzo-18-crown-6 is a hydrophobic crown ether compound.
Synthesis
4',4''(5'')-Di-tert-butyldibenzo-18-crown-6 (DTBB18C6) was synthesized using 4-tert-butyl catechol (TBC) as starting material, 2,2′-diethylene glycol di(p-touenesulfonate) as cyclization reagent, Cs2CO3 as template, and tetrahydrofuran (THF) as solvent. The reaction was carried out in a sealed environment with nitrogen, and Cs2CO3 was supplemented in three steps. Moreover, it could also be synthesized by improving the electrophilic aromatic substitution of dibenzo-18-crown-6 (DB18C6) using tert-butyl alcohol (TBA) as alkylation reagent, H3PO4 (85 wt %) as catalyst and CH2Cl2 as solvent[1-2].
References
[1] Juan Fan. “Preparation of 4′,4′′(5′′)-Di-tert-butyldibenzo-18-crown-6 Based on Electrophilic Aromatic Substitution.” Chemistry Letters 41 1 (2012): 274–276.
[1] Jun Fan. “Optimization of Synthetic Strategy of 4′4″(5″)-Di-tert-butyldibenzo-18-crown-6 Using Response Surface Methodology.” Organic Process Research & Development 17 3 (2013): 368–374.
Properties of 4',4''(5'')-Di-tert-butyldibenzo-18-crown-6
| Melting point: | 112-116 °C |
| Boiling point: | 533.38°C (rough estimate) |
| Density | 1.0542 (rough estimate) |
| refractive index | 1.6000 (estimate) |
| BRN | 1667522 |
| InChI | InChI=1S/C28H40O6/c1-27(2,3)21-7-9-23-25(19-21)33-17-13-30-14-18-34-26-20-22(28(4,5)6)8-10-24(26)32-16-12-29-11-15-31-23/h7-10,19-20H,11-18H2,1-6H3 |
| EPA Substance Registry System | Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin, 2,13(or 2,14)-bis(1,1-dimethylethyl)-6,7,9,10,17,18,20,21-octahydro- (29471-17-8) |
Safety information for 4',4''(5'')-Di-tert-butyldibenzo-18-crown-6
| Signal word | Warning |
| Pictogram(s) |
 Exclamation Mark Irritant GHS07 |
| GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
| Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 4',4''(5'')-Di-tert-butyldibenzo-18-crown-6
| InChIKey | CVQLBTRJDFZYMS-UHFFFAOYSA-N |
| SMILES | C12OCCOCCOC3=C(C=CC(C(C)(C)C)=C3)OCCOCCOC=1C=CC(C(C)(C)C)=C2 |
4',4''(5'')-Di-tert-butyldibenzo-18-crown-6 manufacturer
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