4-Vinylbenzo-18-crown-6

Base Information

• Chemical Name: 4-Vinylbenzo-18-crown-6
• CAS No.: 39557-71-6
• Molecular Formula: C₁₈H₂₆O₆
• Molecular Weight: 338.401
• Hs Code.: 29329900
• European Community (EC) Number: 634-843-6
• DSSTox Substance ID: DTXSID90369234
• Nikkaji Number: J798.594K
• Wikidata: Q72516321
• ChEMBL ID: CHEMBL1886488
• Mol file: 39557-71-6.mol

Synonyms:4-VINYLBENZO-18-CROWN-6;39557-71-6;18-Vinyl-2,3,5,6,8,9,11,12,14,15-decahydrobenzo[b][1,4,7,10,13,16]hexaoxacyclooctadecine;20-ethenyl-2,5,8,11,14,17-hexaoxabicyclo[16.4.0]docosa-1(18),19,21-triene;18-ethenyl-2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecine;4'-Vinylbenzo-18-crown-6;MLS001170850;CHEMBL1886488;SCHEMBL12764437;DTXSID90369234;HMS2909N23;STL089776;AKOS000519564;AS-35620;SMR000594991;CS-0203392;FT-0709177;Ethyl3-(1,3-Benzodioxol-5-yl)-2-cyanoacrylate;Z56755914;3,4-(1,4,7,10,13,16-Hexaoxahexadecane-1,16-diyl)styrene

Chemical Property of 4-Vinylbenzo-18-crown-6

Chemical Property:

• Appearance/Colour: off-white crystalline powder
• Vapor Pressure: 4.17E-09mmHg at 25°C
• Melting Point: 56-60 °C
• Refractive Index: 1.479
• Boiling Point: 485.4 °C at 760 mmHg
• Flash Point: 199 °C
• PSA: 55.38000
• Density: 1.053g/cm³
• LogP: 2.16720
• Storage Temp.: 2-8°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 338.17293854
• Heavy Atom Count: 24
• Complexity: 325

Purity/Quality:

98%,99%, ^*data from raw suppliers

18-Vinyl-2,3,5,6,8,9,11,12,14,15-decahydrobenzo[b][1,4,7,10,13,16]hexaoxacyclooctadecine 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CC1=CC2=C(C=C1)OCCOCCOCCOCCOCCO2

Technology Process of 4-Vinylbenzo-18-crown-6

There total 7 articles about 4-Vinylbenzo-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: 93.0%

4'-(1-Hydroxyethyl)-benzo-18-crown-6 ether (41757-97-5) → 4-vinylbenzo-18-crown-6 (39557-71-6)

Guidance literature:

pyridinium p-toluenesulfonate; In benzene; for 18h; Heating;

DOI:10.1055/s-1986-31749

Reference yield:

ethene (74-85-1) + 18-bromo-2,3,5,6,8,9,11,12,14,15-decahydrobenzo[b][1,4,7,10,13,16]Hexaoxacyclotetradecene (75460-28-5) → 4-vinylbenzo-18-crown-6 (39557-71-6)

Guidance literature:

With tris-(o-tolyl)phosphine; palladium diacetate; at 60 ℃; for 0.5h;

DOI:10.1039/b309072h

Reference yield:

2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin (14098-24-9) → 4-vinylbenzo-18-crown-6 (39557-71-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / polyphosphoric acid / acetic acid / 60 °C

2: 92 percent / sodium borohydride / ethanol / 18 h / Ambient temperature

3: 93 percent / pyridinium tosylate / benzene / 18 h / Heating

With sodium tetrahydroborate; PPA; pyridinium p-toluenesulfonate; In ethanol; acetic acid; benzene;

DOI:10.1055/s-1986-31749

upstream raw materials:

4'-(1-Hydroxyethyl)-benzo-18-crown-6 ether

ethene

18-bromo-2,3,5,6,8,9,11,12,14,15-decahydrobenzo[b][1,4,7,10,13,16]Hexaoxacyclotetradecene

2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin

Refernces

• 1、 Talma, Auke G.,Vossen, Huib van,Sudhoelter, Ernst J. R.,Eerden, Johan van,Reinhoudt, David N.. "Synthesis of 4'-Vinylbenzo-3n-crown-n Ethers (4<=n<=10)". . p. 680 - 683. Retrieved 2007/10/02.