Benzofuran-4-carbonitrile

Base Information

• Chemical Name: Benzofuran-4-carbonitrile
• CAS No.: 95333-17-8
• Molecular Formula: C9H5NO
• Molecular Weight: 143.14200
• DSSTox Substance ID: DTXSID001313266
• Mol file: 95333-17-8.mol

Synonyms:BENZOFURAN-4-CARBONITRILE;95333-17-8;4-BENZOFURANCARBONITRILE;1-BENZOFURAN-4-CARBONITRILE;MFCD10699413;SCHEMBL506731;VCQONKRSTAUGEP-UHFFFAOYSA-N;DTXSID001313266;VDA33317;AC2211;AKOS006302748;MB08822;CS-11583;SY025675;A859088

Chemical Property of Benzofuran-4-carbonitrile

Chemical Property:

• Boiling Point: 260.8±13.0 °C(Predicted)
• PSA: 36.93000
• Density: 1.22±0.1 g/cm3(Predicted)
• LogP: 2.30448
• Storage Temp.: 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 143.037113783
• Heavy Atom Count: 11
• Complexity: 193

Purity/Quality:

NLT 98% ^*data from raw suppliers

Benzofuran-4-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C2C=COC2=C1)C#N

Technology Process of Benzofuran-4-carbonitrile

There total 8 articles about Benzofuran-4-carbonitrile 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: 30.0%

zinc(II) cyanide (557-21-1) + 2-(3-bromophenoxy)acetaldehyde diethyl acetal (204452-94-8) → benzofuran-4-carbonitrile (95333-17-8)

Guidance literature:

2-(3-bromophenoxy)acetaldehyde diethyl acetal; In toluene; at 95 ℃; for 4h;

zinc(II) cyanide; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 100 ℃; for 18h; Inert atmosphere;

Reference yield:

copper(l) cyanide + 2-(3-bromophenoxy)acetaldehyde diethyl acetal (204452-94-8) → benzo[b]furan-6-carbonitrile (17450-68-9) + benzofuran-4-carbonitrile (95333-17-8)

Guidance literature:

2-(3-bromophenoxy)acetaldehyde diethyl acetal; With polyphosphoric acid; In toluene; Reflux;

copper(l) cyanide; In N,N-dimethyl-formamide; at 130 ℃; for 4h;

DOI:10.1021/acs.jmedchem.5b01984

Reference yield:

3-Bromophenol (591-20-8) → benzo[b]furan-6-carbonitrile (17450-68-9) + benzofuran-4-carbonitrile (95333-17-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 20 °C

1.2: 90 °C

2.1: polyphosphoric acid / toluene / Reflux

2.2: 4 h / 130 °C

With sodium hydride; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/acs.jmedchem.5b01984

upstream raw materials:

copper(I) cyanide

4-aminobenzofuran

4-nitro-benzofuran

2-(3-bromophenoxy)acetaldehyde diethyl acetal

Downstream raw materials:

4-acetylbenzofuran

Refernces

• 1、 -. "NAPHTHYRIDINE DERIVATIVES AS PRC2 INHIBITORS". . . Retrieved 2020/11/03.
• 2、 -. "Pyrimidone compound and application thereof". . . Retrieved 2019/07/08.