4'-Aminobenzo-18-crown-6

Base Information

• Chemical Name: 4'-Aminobenzo-18-crown-6
• CAS No.: 68941-06-0
• Molecular Formula: C16H25NO6
• Molecular Weight: 327.378
• Hs Code.: 2932.99
• European Community (EC) Number: 636-198-6
• DSSTox Substance ID: DTXSID80942732
• Nikkaji Number: J911.097F
• Wikidata: Q82919747
• ChEMBL ID: CHEMBL1622600
• Mol file: 68941-06-0.mol

Synonyms:4'-Aminobenzo-18-crown-6;68941-06-0;(Benzo-18-crown-6)-4'-ylamine;2,3,5,6,8,9,11,12,14,15-Decahydrobenzo[b][1,4,7,10,13,16]hexaoxacyclooctadecin-18-amine;2,5,8,11,14,17-hexaoxabicyclo[16.4.0]docosa-1(18),19,21-trien-20-amine;2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin-18-amine;205504-06-9;SCHEMBL1247565;CHEMBL1622600;DTXSID80942732;STR04409;MFCD00210009;STL089790;4'-Aminobenzo-18-crown-6, 97%;AKOS001586895;4'-Aminobenzo-18-crown-6, technical;(BENZO-18-CROWN-6)-4-YLAMINE;CS-0203386;FT-0617555;F76330;A922906;SR-01000390241;SR-01000390241-1;3,4-(1,4,7,10,13,16-Hexaoxahexadecane-1,16-diyl)aniline

Chemical Property of 4'-Aminobenzo-18-crown-6

Chemical Property:

• Appearance/Colour: yellowish crystal
• Melting Point: 53-56 °C
• Boiling Point: 511.9 °C at 760 mmHg
• PKA: 4.62±0.20(Predicted)
• Flash Point: 284.1 °C
• PSA: 81.40000
• Density: 1.099 g/cm³
• LogP: 1.68760
• Storage Temp.: 0-6°C
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 0
• Exact Mass: 327.16818752
• Heavy Atom Count: 23
• Complexity: 294

Purity/Quality:

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

4′-Aminobenzo-18-crown-6 technical ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCOCCOC2=C(C=CC(=C2)N)OCCOCCO1

Technology Process of 4'-Aminobenzo-18-crown-6

There total 8 articles about 4'-Aminobenzo-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: 100.0%

4'-nitrobenzo-18-crown-6 (53408-96-1) → 4-aminobenzo-18-crown-6 (68941-06-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1016/S0040-4020(03)00468-X

Reference yield: 43.0%

2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin (14098-24-9) → 4-aminobenzo-18-crown-6 (68941-06-0)

Guidance literature:

With O-(4-nitrobenzoyl)hydroxylammonium trifluoromethanesulfonate; iron(II) bromide; silver(I) triflimide; In 2,2,2-trifluoroethanol; water; at 30 ℃; for 2h;

DOI:10.1002/chem.201605476

Reference yield:

1,2-dihydroxy-4-nitrobenzene (3316-09-4) → 4-aminobenzo-18-crown-6 (68941-06-0)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium tetrafluoroborate; potassium carbonate / acetonitrile / 84 h / Reflux

2: hydrazine hydrate; palladium 10% on activated carbon / 1,4-dioxane / 3 h / Reflux

With palladium 10% on activated carbon; potassium carbonate; hydrazine hydrate; potassium tetrafluoroborate; In 1,4-dioxane; acetonitrile;

DOI:10.1021/jacs.1c05750

upstream raw materials:

4'-nitrobenzo-18-crown-6

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

2,2'-(1,2-phenylenedioxy)diethanol

1,2-di(2-hydroxyethoxy)-4-nitrobenzene

Downstream raw materials:

4'-Picrylaminobenzo-18-crown-6

Butyl-[4-(6,7,9,10,12,13,15,16,18,19-decahydro-5,8,11,14,17,20-hexaoxa-benzocyclooctadecen-2-ylazo)-phenyl]-amine

N-(6,7,9,10,12,13,15,16,18,19-decahydro-5,8,11,14,17,20-hexaoxa-benzocyclooctadecen-2-yl)-3-nitro-benzamide

Refernces

• 1、 Dykes, Graham M.,Smith, David K.. "Supramolecular dendrimer chemistry: Using dendritic crown ethers to reversibly generate functional assemblies". . p. 3999 - 4009. Retrieved 2003.
• 2、 Sun, Zhan-Hu,Pan, Fang-Fang,Triyanti,Albrecht, Markus,Raabe, Gerhard. "Salt-solubilization and ion-pair recognition by a quinoline-substituted crown ether". . p. 7922 - 7932. Retrieved 2013.
• 3、 Jagleniec, Damian,Romański, Jan,Wilczek, Marcin. "Tripodal, squaramide‐based ion pair receptor for effective extraction of sulfate salt". . . Retrieved 2021/05/28.
• 4、 Jagleniec, Damian,Dobrzycki, ?ukasz,Karbarz, Marcin,Romański, Jan. "Ion-pair induced supramolecular assembly formation for selective extraction and sensing of potassium sulfate". . p. 9542 - 9547. Retrieved 2019/11/11.