Benzo-18-crown-6

Base Information

• Chemical Name: Benzo-18-crown-6
• CAS No.: 14098-24-9
• Molecular Formula: C16H24O6
• Molecular Weight: 312.363
• Hs Code.: 29329985
• European Community (EC) Number: 604-215-6
• DSSTox Substance ID: DTXSID50878074
• Nikkaji Number: J151.277C
• Wikidata: Q72445363
• ChEMBL ID: CHEMBL493574
• Mol file: 14098-24-9.mol

Synonyms:Benzo-18-crown-6;14098-24-9;Benzo-18-crown 6-Ether;MFCD00062741;2,5,8,11,14,17-hexaoxabicyclo[16.4.0]docosa-1(22),18,20-triene;2,3,5,6,8,9,11,12,14,15-Decahydrobenzo[b][1,4,7,10,13,16]hexaoxacyclooctadecine;1,4,7,10,13,16-Benzohexaoxacyclooctadecin, 2,3,5,6,8,9,11,12,14,15-decahydro-;2,3,5,6,8,9,11,12,14,15-Decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecine;benzo-18-crown-6 ether;B18C6-benzo crown ether;Monobenzo-18-crown-6;2,3-Benzo-18-crown-6;YSZC823;SCHEMBL687476;Benzo-18-crown-6, 98%;2,3-Benzo-1,4,7,10,13,16-hexaoxaoctadec-2-ene;CHEMBL493574;DTXSID50878074;AKOS015889751;AS-73449;SY011463;AM20020476;B1539;CS-0155887;FT-0622698;A807712;J-007438;2,3,5,6,8,9,11,12,14,15-Decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecine #

Chemical Property of Benzo-18-crown-6

Chemical Property:

• Appearance/Colour: white granular powder and chunks
• Vapor Pressure: 6.31E-08mmHg at 25°C
• Melting Point: 42-45 °C(lit.)
• Refractive Index: 1.456
• Boiling Point: 451.8 °C at 760 mmHg
• Flash Point: 186.6 °C
• PSA: 55.38000
• Density: 1.057 g/cm³
• LogP: 1.52420
• Storage Temp.: Store below +30°C.
• Sensitive.: Hygroscopic
• Solubility.: very faint turbidity in Methanol
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 312.15728848
• Heavy Atom Count: 22
• Complexity: 237

Purity/Quality:

97% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 22-24/25-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1COCCOCCOC2=CC=CC=C2OCCOCCO1

Technology Process of Benzo-18-crown-6

There total 33 articles about Benzo-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: 95.0%

18-bromo-2,3,5,6,8,9,11,12,14,15-decahydrobenzo[b][1,4,7,10,13,16]Hexaoxacyclotetradecene (75460-28-5) → 2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin (14098-24-9)

Guidance literature:

With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon; In 1,2-dichloro-ethane; at 50 ℃; for 1.5h;

DOI:10.1002/adsc.201901099

Reference yield: 90.4%

o-hydroxyphenyl 3,6,9,12-tetraoxa-14-bromotetradecyl ether (77963-49-6) → 2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin (14098-24-9)

Guidance literature:

With tetramethyl ammoniumhydroxide; In water; dimethyl sulfoxide; at 25 ℃;

DOI:10.1021/ja00404a027

Reference yield: 77.0%

penta(ethylene glycol) bis(p-toluenesulfonate) (41024-91-3) + benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) → 2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin (14098-24-9)

Guidance literature:

With sodium hydroxide; tetra-(n-butyl)ammonium iodide; In toluene; for 16h; Heating;

DOI:10.1055/s-2002-34853

upstream raw materials:

o-hydroxyphenyl 3,6,9,12-tetraoxa-14-bromotetradecyl ether

penta(ethylene glycol) bis(p-toluenesulfonate)

benzene-1,2-diol

pentaethylene glycol dimesylate

Downstream raw materials:

2,3,6,7,10,11-hexamethoxytriphenylene

C₃₂H₃₈O₁₀

(Dibenzo-18-Krone-6-aether)*(Thioharnstoff)

4-Benzoylbenzo<18>krone-6

Refernces

• 1、 Vitali, Chiara Antonini,Masci, Bernardo. "Competition between Catalysts and Inhibitors in Crown Ether Formation and Other Reactions of Associated Substrates". . p. 1070 - 1071. Retrieved 1989.
• 2、 van Keulen,B.J. et al.. "". . p. 285 - 286. Retrieved 1979.
• 3、 Ercolani, Gianfranco,Mandolini, Luigi,Masci, Bernardo. "Template Effects. 3. The Quantiative Determination of the Catalytic Effects of Alkali and Alkaline Earth Cations in the Formation of Benzo-18-crown-6 in Methanol Solution". . p. 2780 - 2782. Retrieved 1981.
• 4、 Bogaschenko, Tatyana,Basok, Stepan,Kulygina, Catherine,Lyapunov, Alexander,Lukyanenko, Nikolay. "A practical synthesis of benzocrown ethers under phase-transfer catalysis conditions". . p. 2266 - 2270. Retrieved 2007/10/03.