4',4''(5'')-Di-tert-butyldibenzo-18-crown-6 Chemical Properties

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

InChIKey

CVQLBTRJDFZYMS-UHFFFAOYSA-N

SMILES

C12OCCOCCOC3=C(C=CC(C(C)(C)C)=C3)OCCOCCOC=1C=CC(C(C)(C)C)=C2

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

Hazard Codes 

Xi

Risk Statements 

36/37/38-36/38-22

Safety Statements 

26-36-36/37

RIDADR 

2811

WGK Germany 

3

RTECS 

HP5386500

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29329990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4',4''(5'')-Di-tert-butyldibenzo-18-crown-6 Usage And Synthesis

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

Uses

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.

4',4''(5'')-Di-tert-butyldibenzo-18-crown-6(29471-17-8)Related Product Information

• 18-Crown-6
• 4,4'-DI-TERT-BUTYLDIBENZO-18-CROWN-6 = AR,AR'-DI-TERT-BUTYLDIBENZO-18-CROWN-6
• O,O'-BIS(2-HYDROXYETHOXY)BENZENE
• 2-(4-tert-butylphenoxy)ethanol
• 4',4''(5'')-DI-TERT-BUTYLDIBENZO-18-CROWN-6
• 1,5-BIS(O-HYDROXYPHENOXY)-3-OXAPENTANE
• tert-Butylcatechol
• Dibenzo-18-crown-6
• 2-(2-HYDROXYETHOXY)PHENOL
• 3-tert-Butylphenol