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Cas Database

14187-32-7

14187-32-7

Identification

  • Product Name:Dibenzo-18-crown-6

  • CAS Number: 14187-32-7

  • EINECS:238-041-3

  • Molecular Weight:360.407

  • Molecular Formula: C20H24O6

  • HS Code:29329995

  • Mol File:14187-32-7.mol

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);

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi,HarmfulXn

  • Hazard Codes:Xi,Xn

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:Dibenzo-18-crown-6
  • Packaging:100mg
  • Price:$ 60
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Dibenzo-18-crown 6-Ether >99.0%(GC)
  • Packaging:25g
  • Price:$ 55
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Dibenzo-18-crown 6-Ether >99.0%(GC)
  • Packaging:5g
  • Price:$ 11
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Dibenzo-18-crown-6
  • Packaging:5 g
  • Price:$ 20
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Dibenzo-18-crown-6
  • Packaging:1 g
  • Price:$ 15
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Dibenzo-18-crown-6
  • Packaging:25 g
  • Price:$ 35
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  • Manufacture/Brand:Strem Chemicals
  • Product Description:Dibenzo-18-crown-6, min. 98%
  • Packaging:10g
  • Price:$ 61
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  • Manufacture/Brand:Strem Chemicals
  • Product Description:Dibenzo-18-crown-6, min. 98%
  • Packaging:50g
  • Price:$ 212
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Crown ether/Dibenzo-18-crown-6 for synthesis. CAS 14187-32-7, molar mass 360.41 g/mol., for synthesis
  • Packaging:8117310050
  • Price:$ 188
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Crown ether/Dibenzo-18-crown-6 for synthesis
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Relevant articles and documentsAll total 12 Articles be found

Lead ion selective electrodes from dibenzo-18-crown-6 derivatives: An exploratory study

Jackson, Deneikah T.,Nelson, Peter N.,Booysen, Irvin N.

, (2020/11/16)

Dibenzo-18-crown-6 (DB18C6) and three of its derivatives (-COCH3, -Br, -NO2), are investigated via Density Functional Theoretical (DFT) modelling, Fourier Transform Infrared (FT-IR) and absorption spectroscopies, Differential Pulse Anodic Stripping (DPASV), Cyclic (CV) and Square Wave (SWV) voltammetries, as possible materials for preparing plasticiser free lead(II) ion selective electrodes. The spontaneous, entropy driven, interactions between lead(II) ions and DB18C6 derivatives are such that they form 1:1 complexes via coordination with the high electron density open ether cavity, except for the brominated derivative where the metal: ligand stoichiometry is 2:1 due to exo-cavity coordination via the high electron density bromine atoms. Monolayers resulting from electropolymerization of some derivatives (-H, -COCH3, -Br) and chemisorption of the -NO2 derivative, allows quantification of lead(II) ions at concentrations below 10 mg L?1 with minimal interference from other metal ions except Hg2+ and Al3+.

Crown Ether-Functionalized Polybenzoxazine for Metal Ion Adsorption

Mohamed, Mohamed Gamal,Kuo, Shiao-Wei

, p. 2420 - 2429 (2020/03/26)

In this study, we synthesized a new crown ether-functionalized benzoxazine monomer (crown-ether BZ) in high yield and purity through reduction of the Schiff base prepared from a dibenzo[18]crown-6 diamine derivative and salicylaldehyde and subsequent reaction of the resulting o-hydroxybenzylamine species with CH2O. We used differential scanning calorimetry (DSC), Fourier transform infrared (FTIR) spectroscopy, and thermogravimetric analysis to examine the thermal ring opening polymerization and thermal stability of the crown-ether BZ monomer during various types of thermal treatment. DSC revealed that this crown-ether BZ monomer featured a relatively low curing temperature (210 °C; that of the typical Pa-type 3-phenyl-3,4-dihydro-2H-benzooxazine monomer: 263 °C) because the flexibility of the crown ether moiety on the main chain backbone structure catalyzed the ring opening polymerization. We also used DSC, FTIR spectroscopy, and ionic conductivity measurements to investigate the specific metal-crown ether interactions of crown-ether BZ/LiClO4 complexes. The presence of Li+ ions decreased the curing temperature significantly to 186 °C, suggesting that the metal ions functioned as an effective catalyst and promoter that accelerated the ring opening polymerization of the crown-ether BZ monomer. The ionic conductivity reached 8.3 × 10-5 S cm-1 for the crown-ether BZ/LiClO4 = 90/10 complex after thermal c? this value is higher than those of typical polymer-based systems (e.g., PEO, PCL, PMMA, and PVP) while also providing a polymer electrolyte of higher thermal stability.

Dibenzo - 18 - crown - 6 ring metal iridium complex and its application

-

Paragraph 0048-0050, (2017/11/16)

The invention discloses an electrophosphorescent material containing a dibenzo-18-crown-6-based cyclometalated iridium complex, and an application thereof in a polymer electroluminescent device. According to the cyclometalated iridium complex disclosed by the invention, because dibenzo-18-crown-6 has a quite high steric hindrance, intermolecular aggregation can be effectively reduced, thus avoiding a triplet-triplet (T-T) quenching effect. Meanwhile, the dibenzo-18-crown-6 group has an electron transmission capacity to a certain extent and is capable of effectively adjusting the electron injection and transmission capacities of the iridium complex, thus greatly improving the luminescent performance of the material in the electroluminescent device. The cyclometalated iridium complex disclosed by the invention can be used as a green luminescent material and applied to an organic electroluminescent device, thus providing a new way for obtaining an efficient organic electrophosphorescent material.

Application of Bayer-Villiger reaction to the synthesis of dibenzo-18-crown-6, dibenzo-21-crown-7 and dihydroxydibenzo-18-crown-6

Utekar, Druman R.,Samant, Shriniwas D.

, p. 193 - 197 (2014/05/06)

Dibenzo-18-crown-6, dibenzo-21-crown-7 and dihydroxy dibenzo-18-crown-6 were synthesized by Bayer-Villiger oxidation strategy. Dibenzo-18-crown-6 and dibenzo-21-crown-7 could be synthesized through a three-step protocol starting from salicylaldehyde. Salicylaldehyde was reacted with bis-(2-chloroethyl)ether using K2CO3 in acetonitrile to link the two phenolic groups with the oxyethylene bridge followed by conversion of the formyl group to the hydroxy group via a Baeyer-Villiger reaction and finally linking the two phenolic group with appropriate oxyethylene bridge. The two target crown ethers were obtained in overall yield, 24% and 30%, respectively. This method has a great potential for synthesis of symmetrical as well as unsymmetrical dibenzo crowns with varying oxyethylene bridges. Baeyer-Villiger oxidation could be used to prepare dihydroxy derivative of dibenzo-18-crown-6 through acetylation of dibenzo-18-crown-6 followed by Baeyer-Villiger oxidation. The Baeyer-Villiger oxidation could be substantially accelerated using trifluoroacetic acid.

Microwave-assisted synthesis of dibenzo-crown ethers

Torrejos, Rey Eliseo C.,Nisola, Grace M.,Beltran, Arnel B.,Park, Myoung Jun,Patil, Basavaraj R.,Lee, Seong-Poong,Seo, Jeong Gil,Chung, Wook-Jin

, p. 109 - 115 (2014/03/21)

Microwave-assisted organic synthesis (MAOS) for dibenzo-substituted crown ethers is presented. Two routes were developed: (1) one-pot MAOS for symmetric dibenzo-crown ethers (DBC) and (2) a two-step MAOS via diphenol intermediates for both symmetric and asymmetric DBCs. MAOS were carried out in open or closed vessels, with or without temperature control at various microwave settings using different bases and reactants. Open vessel MAOS was limited by the volatility of reactants hence was less preferred than the closed vessel MAOS. DBC formation was highly affected by the cation size of the base, which acted as a template ion during DBCs ring closure. Closed vessel MAOS without temperature control was found most appropriate for DBC synthesis. Symmetric DBCs were conveniently obtained via one-pot MAOS whereas asymmetric DBCs were obtained from two-step MAOS via diphenol intermediates. The method was found expedient as it afforded satisfactory yields at considerably shorter reaction time than those in conventional methods.

Process route upstream and downstream products

Process route

C<sub>20</sub>H<sub>24</sub>O<sub>6</sub>*C<sub>8</sub>H<sub>20</sub>N<sub>2</sub>*2ClH

C20H24O6*C8H20N2*2ClH

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

1,8-diaminooctane dihydrochloride
7613-16-3,68192-88-1

1,8-diaminooctane dihydrochloride

Conditions
Conditions Yield
In water; at 25 ℃; Equilibrium constant;
bis(2-hydroxyphenoxyethyl)ether
23116-94-1

bis(2-hydroxyphenoxyethyl)ether

3-oxa-1,5-dichloropentane
111-44-4

3-oxa-1,5-dichloropentane

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

Conditions
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; Yield given. Multistep reaction; 1.) n-BuOH, MeOH, 2.) n-BuOH, reflux, 17 h;
3-oxa-1,5-dichloropentane
111-44-4

3-oxa-1,5-dichloropentane

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

Conditions
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%
benzene-1,2-diol; 3-oxa-1,5-dichloropentane; With sodium hydroxide; In butan-1-ol; at 90 ℃; for 2h; Heating;
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;
3-oxa-1,5-dichloropentane
111-44-4

3-oxa-1,5-dichloropentane

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

1,2-bis[2'-(2''-chloroethoxy)ethoxy]benzene
41758-00-3

1,2-bis[2'-(2''-chloroethoxy)ethoxy]benzene

2-(5-chloro-3-oxa-1-pentyloxy)phenol
111875-63-9

2-(5-chloro-3-oxa-1-pentyloxy)phenol

Conditions
Conditions Yield
With potassium hydroxide; In dimethyl sulfoxide; at 90 ℃; for 2.5h; Yields of byproduct given;
55%
diethylene glycol disodium salt

diethylene glycol disodium salt

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

Conditions
Conditions Yield
With iodine; tetrabutylammomium bromide; Yield given. Multistep reaction;
dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: sodium hydroxide / dimethyl sulfoxide / 0.08 h / Microwave irradiation
2: potassium hydroxide / dimethyl sulfoxide / 0.08 h / Microwave irradiation
With potassium hydroxide; sodium hydroxide; In dimethyl sulfoxide;
salicylaldehyde
90-02-8

salicylaldehyde

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: potassium carbonate / acetonitrile / 48 h / 85 °C
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 25 °C
3: potassium carbonate / acetonitrile / 36 h / 85 °C
With potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile;
1,5-bis(benzaldehydeoxy)-3-oxopentane
82645-24-7

1,5-bis(benzaldehydeoxy)-3-oxopentane

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 25 °C
2: potassium carbonate / acetonitrile / 36 h / 85 °C
With potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile;
C<sub>20</sub>H<sub>24</sub>O<sub>6</sub>*NO<sub>3</sub><sup>(1-)</sup>*Rb<sup>(1+)</sup>

C20H24O6*NO3(1-)*Rb(1+)

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

Conditions
Conditions Yield
With rubidium nitrate; In acetonitrile; at 15 - 45 ℃; Equilibrium constant; Thermodynamic data;
C<sub>20</sub>H<sub>24</sub>O<sub>6</sub>*Cs<sup>(1+)</sup>*NO<sub>3</sub><sup>(1-)</sup>

C20H24O6*Cs(1+)*NO3(1-)

dibenzo-18-crown-6
14187-32-7

dibenzo-18-crown-6

Conditions
Conditions Yield
With caesium nitrate; In acetonitrile; at 15 - 45 ℃; Equilibrium constant; Thermodynamic data;

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