3-Aminodibenzofuran

Base Information

• Chemical Name: 3-Aminodibenzofuran
• CAS No.: 4106-66-5
• Molecular Formula: C12H9 N O
• Molecular Weight: 183.21
• Hs Code.: 2932999099
• European Community (EC) Number: 809-248-1
• NSC Number: 89128
• UNII: 2QMB22RU9N
• DSSTox Substance ID: DTXSID3020411
• Nikkaji Number: J34.845G
• Wikidata: Q27255486
• ChEMBL ID: CHEMBL1622337
• Mol file: 4106-66-5.mol

Synonyms:3-aminodibenzofuran

Chemical Property of 3-Aminodibenzofuran

Chemical Property:

• Vapor Pressure: 1.21E-05mmHg at 25°C
• Melting Point: 94°C
• Refractive Index: 1.5880 (estimate)
• Boiling Point: 369.1°Cat760mmHg
• PKA: 3.78±0.30(Predicted)
• Flash Point: 177°C
• PSA: 39.16000
• Density: 1.283g/cm³
• LogP: 3.74940
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 183.068413911
• Heavy Atom Count: 14
• Complexity: 218

Purity/Quality:

97% ^*data from raw suppliers

Dibenzo[b,d]furan-3-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C3=C(O2)C=C(C=C3)N
• Uses: 3-Aminodibenzofuran is a building block used as a reactant in the preparaton of dibenzofuryl(phosphonomethyl)alanines as endothelin converting enzyme inhibitors. Dibenzo[b,d]furan-3-amine is a building block used as a reactant in the preparaton of dibenzofuryl(phosphonomethyl)alanines as endothelin converting enzyme inhibitors.

Technology Process of 3-Aminodibenzofuran

There total 2 articles about 3-Aminodibenzofuran 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:

3,3'-Diiododiphenylene oxide (137959-93-4) + ammonia (7664-41-7) + sodium amide → 3-aminodibenzofuran (4106-66-5) + diethyl ether (60-29-7,927820-24-4)

Guidance literature:

DOI:10.1021/ja01219a001

Reference yield:

dibenzofuran (132-64-9,214827-48-2) → 3-aminodibenzofuran (4106-66-5) + 1-aminodibenzofuran (50548-40-8)

Guidance literature:

With 1,10-Phenanthroline; cesiumhydroxide monohydrate; copper(II) bis(trifluoromethanesulfonate); hydroxylamine-O-sulfonic acid; at 20 ℃; for 6h; Overall yield = 73 %; Overall yield = 78 mg; Inert atmosphere;

DOI:10.1021/acs.orglett.9b00586

Reference yield: 84.9%

3-aminodibenzofuran (4106-66-5) + 9-(phenyl)-2-bromo-9H-carbazole (94994-62-4) → C30H20N2O

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate; XPhos; In toluene; at 70 ℃; for 1h; Inert atmosphere;

upstream raw materials:

3,3'-Diiododiphenylene oxide

ammonia

dibenzofuran

Refernces

Copper(I)-catalyzed Cyclization Reactions of Ethyl (E)-α-Ethynyl-β-Aryl-α,β-Unsaturated Esters with N-Sulfonyl Azides: Synthesis of 1-Aminonaphthalene, 3-Aminobenzofuran, and 3-Aminothiobenzofuran Derivatives

10.1002/bkcs.11755

The study presents a synthetic method for the preparation of ethyl 4-(alkyl or arylsulfonamido)-2-naphthoates, which are derivatives of 1-aminonaphthalene, 3-aminobenzofuran, and 3-aminobenzothiophene. These compounds are significant due to their presence in biologically active molecules used in cancer treatment and as inhibitors for various enzymes. The synthesis involves a copper(I)-catalyzed cyclization reaction of ethyl (E)-α-ethynyl-β-aryl-α,β-unsaturated esters with N-sulfonyl azides in the presence of 2,6-lutidine in THF at 60°C for 3 hours. This method efficiently produces a wide range of the aforementioned derivatives with the release of molecular nitrogen. The chemicals used in the study include ethyl (E)-α-ethynyl-β-aryl-α,β-unsaturated esters as starting materials, N-sulfonyl azides as reactants, 2,6-lutidine as a base, and copper(I) as a catalyst, all serving specific roles in the cyclization reaction to form the desired aminonaphthalene and related derivatives.