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

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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

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.