Dibenzo-18-crown-6

Base Information

• Chemical Name: Dibenzo-18-crown-6
• CAS No.: 14187-32-7
• Deprecated CAS: 54765-16-1,63172-39-4,66105-26-8,73128-69-5,63172-39-4,66105-26-8,73128-69-5
• Molecular Formula: C20H24O6
• Molecular Weight: 360.407
• Hs Code.: 29329995
• European Community (EC) Number: 238-041-3
• NSC Number: 147771
• UNII: 0A7W45JCS9
• DSSTox Substance ID: DTXSID6022428
• Nikkaji Number: J14.747H
• Wikipedia: Dibenzo-18-crown-6
• Wikidata: Q5272256
• Metabolomics Workbench ID: 52751
• ChEMBL ID: CHEMBL345536
• Mol file: 14187-32-7.mol

Synonyms:dibenzo-18-crown-6;polyether XXVIII

Chemical Property of Dibenzo-18-crown-6

Chemical Property:

• Appearance/Colour: white to slightly beige fluffy powder
• Vapor Pressure: 3.65E-10mmHg at 25°C
• Melting Point: 162-164 °C(lit.)
• Refractive Index: 1.5
• Boiling Point: 503.1 °C at 760 mmHg
• Flash Point: 206 °C
• PSA: 55.38000
• Density: 1.108 g/cm³
• LogP: 2.94880
• Storage Temp.: Store below +30°C.
• Sensitive.: air sensitive
• Solubility.: 0.007g/l
• Water Solubility.: sparingly soluble
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 360.15728848
• Heavy Atom Count: 26
• Complexity: 300

Purity/Quality:

99.0% min ^*data from raw suppliers

Dibenzo-18-crown-6 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36-36/37/38-20/21/22
• Safety Statements: 26-37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: C1COC2=CC=CC=C2OCCOCCOC3=CC=CC=C3OCCO1
• Uses: Dibenzo-18-crown-6, is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. It is an important organic intermediate. Crown ether/Dibenzo-18-crown-6 for synthesis. CAS 14187-32-7, molar mass 360.41 g/mol.

Technology Process of Dibenzo-18-crown-6

There total 15 articles about Dibenzo-18-crown-6 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) + 3-oxa-1,5-dichloropentane (111-44-4) → dibenzo-18-crown-6 (14187-32-7)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; for 0.0833333h; Microwave irradiation;

DOI:10.2174/15701786113106660075

Reference yield: 73.0%

bis(2-hydroxyphenoxyethyl)ether (23116-94-1) + 3-oxa-1,5-dichloropentane (111-44-4) → dibenzo-18-crown-6 (14187-32-7)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; for 0.0833333h; Microwave irradiation;

DOI:10.2174/15701786113106660075

Reference yield: 55.0%

benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) + 3-oxa-1,5-dichloropentane (111-44-4) → dibenzo-18-crown-6 (14187-32-7) + 1,2-bis[2'-(2''-chloroethoxy)ethoxy]benzene (41758-00-3) + 2-(5-chloro-3-oxa-1-pentyloxy)phenol (111875-63-9)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; at 90 ℃; for 2.5h; Yields of byproduct given;

upstream raw materials:

bis(2-hydroxyphenoxyethyl)ether

3-oxa-1,5-dichloropentane

benzene-1,2-diol

salicylaldehyde

Downstream raw materials:

2:1 complex of 2,4,6-trinitrophenol with dibenzo-18-crown-6

1-(14-Propionyl-6,7,9,10,17,18,20,21-octahydro-5,8,11,16,19,22-hexaoxa-dibenzo[a,j]cyclooctadecen-2-yl)-propan-1-one

4',4''(5'')-dipropionyl-dibenzo-18-crown-6

ternary complex of 2,3-dichloro-5,6-dicyano-p-benzoquinone, dibenzo-18-crown-6 and t-butylammonium perchlorate

Refernces

• 1、 Fan, Juan,Yi, Chunhai,Lan, Xiaorong,Yang, Bolun. "Preparation of 4′,4″ (5″)-Di-tert-butyldibenzo-18-crown-6 based on electrophilic aromatic substitution". . p. 274 - 276. Retrieved 2012.
• 2、 Baldoli, Clara,Buttero, Paola Del,Maiorana, Stefano,Papagni, Antonio. "Aromatic Nucleophilic Substituation of Cr(CO)3-complexed Halogenoarenes: A New Entry to Dibenzo Crown Ethers". . p. 1181 - 1182. Retrieved 1985.
• 3、 Kyba et al.. "". . p. 2564,2570. Retrieved 1977.
• 4、 -. "Dibenzo - 18 - crown - 6 ring metal iridium complex and its application". Paragraph 0048-0050. . Retrieved 2017/11/16.