2-(Aminomethyl)benzofuran

Base Information

• Chemical Name: 2-(Aminomethyl)benzofuran
• CAS No.: 37798-05-3
• Molecular Formula: C9H9NO
• Molecular Weight: 147.177
• Hs Code.: 2932999099
• ChEMBL ID: CHEMBL4578553
• DSSTox Substance ID: DTXSID90597873
• Nikkaji Number: J2.514.377I
• Pharos Ligand ID: S1TVDYZXR16X
• Wikidata: Q82493532
• Mol file: 37798-05-3.mol

Synonyms:37798-05-3;2-(Aminomethyl)benzofuran;1-benzofuran-2-ylmethanamine;benzofuran-2-ylmethanamine;(Benzofuran-2-yl)methanamine;(1-benzofuran-2-yl)methanamine;MFCD00052743;1-(1-Benzofuran-2-yl)methanamine;aminomethylbenzofuran;(benzofuran-2-ylmethyl)amine;SCHEMBL533908;CHEMBL4578553;DTXSID90597873;DLUXAKYABIDWMU-UHFFFAOYSA-N;AC2210;AKOS000182889;SB22933;BS-13461;SY026572;DB-264368;CS-0186434;EN300-53869;2-(1,3-BENZODIOXOL-5-YLOXY)NICOTINICACID;A882377;A924214;J-501790

Chemical Property of 2-(Aminomethyl)benzofuran

Chemical Property:

• PSA: 39.16000
• LogP: 2.59180
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 147.068413911
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

97% ^*data from raw suppliers

1-Benzofuran-2-ylmethanamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(O2)CN
• General Description: Benzofuran-2-ylmethanamine is a structurally significant compound that serves as a key intermediate in the synthesis of biologically active molecules. It can be synthesized through a novel method involving ortho-methoxy substituted phenylacetic acids, with key intermediates featuring oxazole-4-carboxylic acid methylester moieties. The process employs reagents like HBr/HAc and is particularly effective with electron-donating substituents, though it faces limitations with electron-withdrawing groups. This synthetic approach offers a versatile route for producing benzofuran-2-ylmethanamine derivatives, highlighting its potential in medicinal and organic chemistry applications.

Technology Process of 2-(Aminomethyl)benzofuran

There total 11 articles about 2-(Aminomethyl)benzofuran 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%

2-benzofurancarboxaldehyde oxime (114354-16-4) → benzofuran-2-ylmethanamine (37798-05-3)

Guidance literature:

With ammonia; zinc; In ethanol; water; at 20 ℃; for 2h;

DOI:10.1002/adsc.201801225

Reference yield: 82.0%

→ benzofuran-2-ylmethanamine (37798-05-3)

Guidance literature:

Reference yield: 77.0%

2-(benzofuran-2-ylmethyl)isoindoline-1,3-dione (933068-91-8) → benzofuran-2-ylmethanamine (37798-05-3)

Guidance literature:

With hydrazine hydrate; In ethanol; for 2h; Heating;

DOI:10.1016/j.tet.2007.07.096

upstream raw materials:

2-(benzofuran-2-ylmethyl)isoindoline-1,3-dione

2-benzofurancarboxaldehyde oxime

2-benzofuran carbaldehyde oxime

benzofuran-2-carboxamide

Downstream raw materials:

3-[(benzofuran-2-ylmethyl)-amino]-propionic acid benzyl ester

Refernces

Novel synthesis of benzofuran- and indol-2-yl-methanamine derivatives

10.1016/j.tetlet.2014.11.015

The study presents a novel synthetic method for the production of benzofuran-2-yl-methanamine and indol-2-yl-methanamine derivatives, which are significant in synthetic strategies due to their presence in biologically active compounds. The synthesis involves the use of ortho-methoxy and ortho-nitro substituted phenylacetic acids as starting materials, respectively. Key intermediates in this process are compounds bearing the oxazole-4-carboxylic acid methylester moiety. The study details the synthesis process, which includes the use of reagents such as HBr/HAc for the production of benzofuran-2-yl-methanamines and HCl for the synthesis of indol-2-yl-methanamines after the reduction of the nitro-group. The method is effective with electron-donating substituents but has limitations with electron-withdrawing substituents. The study also discusses the availability and preparation of the starting phenylacetic acids and explores the synthetic procedure's applicability to a variety of substituted phenylacetic acids, demonstrating its potential as a general synthetic method for these compounds.