Benzo-15-crown-5

Base Information

• Chemical Name: Benzo-15-crown-5
• CAS No.: 14098-44-3
• Molecular Formula: C14H20O5
• Molecular Weight: 268.31
• Hs Code.: 29329995
• European Community (EC) Number: 237-947-6
• NSC Number: 175877
• DSSTox Substance ID: DTXSID70161511
• Nikkaji Number: J151.265J
• Wikidata: Q27117143
• Metabolomics Workbench ID: 55573
• ChEMBL ID: CHEMBL158353
• Mol file: 14098-44-3.mol

Synonyms:Benzo-15-crown-5;14098-44-3;2,3,5,6,8,9,11,12-Octahydrobenzo[b][1,4,7,10,13]pentaoxacyclopentadecine;Benzo-15-crown 5-Ether;Benzyl 15-crown-5;Monobenzo-15-crown-5;Benzo15C5;Denzo15C5;2,3,5,6,8,9,11,12-Octahydro-1,4,7,10,13-benzopentaoxacyclopentadecine;1,4,7,10,13-Benzopentaoxacyclopentadecin, 2,3,5,6,8,9,11,12-octahydro-;CCRIS 3608;2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(19),15,17-triene;EINECS 237-947-6;Benzo-15-crown-5 ether;Benzo[6]1,4,7,10,13-pentaoxacyclopentadecane;BRN 1624106;2,3,5,6,8,9,11,12-Octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin;CHEBI:37444;2,3,5,6,8,9,11,12-Octahydrobenzo-[b][1,4,7,10,13]pentaoxacyclopentadecine;MFCD00005945;NSC175877;benzo 15-crown-5 ether;2,3-Benzo-15-crown-5;SCHEMBL603441;Benzo-15-crown-5, 98%;CHEMBL158353;Crown ether benzo-15-crown-5;LCZC3794;DTXSID70161511;BBL011086;STK802303;AKOS005622507;CS-W009301;DS-6427;NSC 175877;NSC-175877;NCGC00166017-01;NCGC00166017-02;LS-38791;AM20020477;B1154;FT-0622697;AB01334247-02;A807713;AH-283/31127055;J-007440;2,3-Benzo-1,4,7,10,13-pentaoxacyclopentadec-2-ene;Q27117143;1,7,10,13-Benzopentaoxacyclopentadecin, 2,3,5,6,8,9,11,12-octahydro-;2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxa cyclopentadecin;Benzo-15-crown-5(2,3,5,6,8,9,11,12-Octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin);Bis(1,4,7,10,13-Benzopentaoxacyclopentadecin, 2,3,5,6,8,9,11,12-Octahydro-)

Chemical Property of Benzo-15-crown-5

Chemical Property:

• Appearance/Colour: Almost white to light grey powder or flakes
• Vapor Pressure: 3.2E-06mmHg at 25°C
• Melting Point: 78-80 °C(lit.)
• Refractive Index: 1.465
• Boiling Point: 399.2 °C at 760 mmHg
• Flash Point: 165.9 °C
• PSA: 46.15000
• Density: 1.068 g/cm³
• LogP: 1.50760
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Water Solubility.: partially soluble
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 268.13107373
• Heavy Atom Count: 19
• Complexity: 202

Purity/Quality:

99% ^*data from raw suppliers

Benzo-15-crown-5 ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCOC2=CC=CC=C2OCCOCCO1
• Uses: Benzo-15-crown-5 is used in synthetic chemistry. It plays a major role and involved in complexation through ether oxygen. It is used in phase-transfer catalyst system. It is involved in 'Host-Guest' chemistry to identify the move of essential elements in the body. It can play the part of very complicated biological reactions such as enzyme functions, which finds application in the development of new pharmaceuticals.

Technology Process of Benzo-15-crown-5

There total 26 articles about Benzo-15-crown-5 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: 92.0%

1,2-bis[2-(2-hydroxyethoxy)ethoxy]benzene (41757-99-7) → 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin (14098-44-3)

Guidance literature:

With sodium hydroxide; p-toluenesulfonyl chloride; In 1,4-dioxane;

Reference yield: 90.1%

o-hydroxyphenyl 3,6,9-trioxa-11-bromoundecyl ether (77963-45-2) → 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin (14098-44-3)

Guidance literature:

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

DOI:10.1021/ja00404a027

Reference yield: 82.097%

1,11-dichloro-3,6,9-trioxaundecane (638-56-2,27252-69-3) + benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) → 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin (14098-44-3)

Guidance literature:

benzene-1,2-diol; With sodium hydroxide; In water; butan-1-ol;

1,11-dichloro-3,6,9-trioxaundecane; at 107 ℃; for 7h;

DOI:10.13005/ojc/330413

upstream raw materials:

1,2-bis[2-(2-hydroxyethoxy)ethoxy]benzene

1,11-dichloro-3,6,9-trioxaundecane

benzene-1,2-diol

tetraethylene glycol di(p-toluenesulfonate)

Downstream raw materials:

4'-(2-phenyl-1-oxoethyl)benzo-15-crown-5

4'-(3,4-Dimethoxyphenylacetyl)benzo-15-crown-5

2-Acetyl-6,7,9,10,12,13,15,16-octahydro-1,4,7,10,13-pentaoxabenzocyclopentadecene

4'-tert-Butylbenzo-15-crown-5

Refernces

BENZOPYRILIUM SALTS WITH A CYCLOPOLYETHER SUBSTITUENT

10.1007/BF00479904

The research focuses on the synthesis of benzo[c]pyrilium salts with a cyclopolyether substituent and their conversion to isoquinoline derivatives. The key chemicals involved in the research include homoveratric acid and benzo-15-crown-5 as starting compounds. These compounds react in polyphosphoric acid to form ketone I. Carboxylic acid anhydrides, specifically acetic or propionic anhydride, along with perchloric acid, are used to convert ketone I into benzo[c]pyrilium perchlorates (IIa and IIb). Finally, ammonium carbamate is employed to transform these perchlorates into the desired isoquinoline derivatives (IIIa and IIIb). The study explores the potential of these compounds for developing new biologically active substances that can penetrate biological membranes or influence selective ion transfer in living organisms.