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:

1-(6,7,9,10,12,13,15,16-Octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-yl)-dodecan-1-one

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

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

2-(11-Hydroxy-3,6,9-trioxaundecyloxy)-4-(5-nitro-2-thiazolyldiazenyl)phenol

Refernces

• 1、 Shen, Ya-Chi,Shih, Jeng-Shong. "Preparation and application of cholesteryl-benzo-15-crown-5/cholesteryl mixed liquid crystals". . p. 578 - 586. Retrieved 2008.
• 2、 Kimura, Masaru,Shi, Kun,Hashimoto, Koji,Hu, Zhi Zhi. "Establishment of an efficient synthetic route to 3,4:3′,4′-bis(3,6,9-trioxaundecane-1,11-dioxy)benzil". . p. 2375 - 2380. Retrieved 2006.
• 3、 Glushko, Valentina N.,Sadovskaya, Natalya Yu.,Kozhuhov, Vadim I.,Blokhina, Lidiya I.,Antropova, Irina A.,Petina, Ekaterina S.,Retiviov, Vasiliy M.,Melnikova, Ekaterina Yu.. "Production of macrocyclic polyether benzo-15-crown-5 and its functional derivatives". . p. 1689 - 1697. Retrieved 2017.
• 4、 Cseri, Tivadar,Bekassy, Sandor,Bodas, Zoltan,Agai, Bela,Figueras, Francois. "Acetylation of B15C5 crown ether on Cu modified clay catalysts". . p. 1473 - 1476. Retrieved 1996.
• 5、 Chen, Yuting,Wang, Xinxin,Wang, Kaili,Zhang, Xiuling. "A benzo-15-crown-5-modifying ratiometric-absorption and fluorescent OFF-ON chemosensor for Cu2 +". . p. 144 - 149. Retrieved 2016/04/04.