4-Aminobenzo-12-crown-4

Base Information

• Chemical Name: 4-Aminobenzo-12-crown-4
• CAS No.: 78554-68-4
• Molecular Formula: C12H18NO4
• Molecular Weight: 239.271
• DSSTox Substance ID: DTXSID801169758
• Nikkaji Number: J1.055.394F
• Mol file: 78554-68-4.mol

Synonyms:4-Aminobenzo-12-crown-4;78554-68-4;2,3,5,6,8,9-hexahydro-1,4,7,10-benzotetraoxacyclododecin-12-amine;2,5,8,11-tetraoxabicyclo[10.4.0]hexadeca-1(12),13,15-trien-14-amine;Oprea1_328669;SCHEMBL16773127;DTXSID801169758;HMS1769K04;CS-M2688;STL089782;AKOS001012444;CS-14632;C12601;SR-01000389286;SR-01000389286-1;3,4-(1,4,7,10-Tetraoxa-1,10-decanediyl)aniline;Z56767629

Chemical Property of 4-Aminobenzo-12-crown-4

Chemical Property:

• Melting Point: 86 - 88 °C
• PSA: 62.94000
• LogP: 1.65440
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 239.11575802
• Heavy Atom Count: 17
• Complexity: 215

Purity/Quality:

NLT 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1COCCOC2=C(C=CC(=C2)N)OCCO1

Technology Process of 4-Aminobenzo-12-crown-4

There total 2 articles about 4-Aminobenzo-12-crown-4 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:

N-boc-3,4-dihydroxyaniline + triethylene glycol di-(p-toluenesulfonate) (19249-03-7) → 6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-ylamine (78554-68-4)

Guidance literature:

N-boc-3,4-dihydroxyaniline; With barium hydroxide; In N,N-dimethyl-formamide; at 90 ℃; for 0.5h; Inert atmosphere;

triethylene glycol di-(p-toluenesulfonate); In N,N-dimethyl-formamide; at 90 ℃; for 4h;

With sulfuric acid; trifluoroacetic acid; In dichloromethane; at 0 - 10 ℃; for 3h;

Reference yield:

triethylene glycol di-(p-toluenesulfonate) (19249-03-7) → 6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-ylamine (78554-68-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrabutylammomium bromide; sodium hydroxide / toluene; water / 0.5 h / 50 - 60 °C

1.2: 6 h / Reflux

2.1: acetic acid; nitric acid / chloroform / 24 h / 20 °C / Cooling with ice

3.1: palladium 10% on activated carbon; hydrogen / ethanol / 24 h

With palladium 10% on activated carbon; tetrabutylammomium bromide; hydrogen; nitric acid; acetic acid; sodium hydroxide; In ethanol; chloroform; water; toluene;

Reference yield: 70.0%

2,4,6-trinitrochlorobenzene (88-88-0) + 6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-ylamine (78554-68-4) → 4'-picrylamino benzo-12-crown-4

Guidance literature:

With sodium hydrogencarbonate; In methanol; Heating;

upstream raw materials:

triethylene glycol di-(p-toluenesulfonate)

Downstream raw materials:

N-(13-(2-phenylethynyl)-2,3,5,6,8,9-hexahydro-1,4,7,10-tetraoxabenzocyclododecen-12-yl)acetamide

N-{13-[2-(4-methoxyphenyl)ethynyl]-2,3,5,6,8,9-hexahydro-1,4,7,10-tetraoxabenzocyclododecen-12-yl}acetamide

N-{13-[2-(4-nitrophenyl)ethynyl]-2,3,5,6,8,9-hexahydro-1,4,7,10-tetraoxabenzocyclododecen-12-yl}acetamide

1⁴-<4-phenyldiazenyl>-2,5,8,11-tetraoxa-1(1,2)-benzenacycloundecaphane

Refernces

• 1、 -. "Preparation method of icotinib key intermediate". Paragraph 0039; 0040; 0041. . Retrieved 2020/07/15.