2-(anthracen-9-yl)benzonitrile

Base Information

• Chemical Name: 2-(anthracen-9-yl)benzonitrile
• CAS No.: 1112197-04-2
• Molecular Formula: C₂₁H₁₃N
• Molecular Weight: 279.341
• Mol file: 1112197-04-2.mol

Synonyms:2-(anthracen-9-yl)benzonitrile

Chemical Property of 2-(anthracen-9-yl)benzonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(anthracen-9-yl)benzonitrile

There total 4 articles about 2-(anthracen-9-yl)benzonitrile 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: 54.0%

9,10-Dibromoanthracene (523-27-3) + 2-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-benzonitrile (214360-47-1) → 9,10-bis(2-cyanophenyl)anthracene (1021601-17-1,1021601-13-7) + 2-(anthracen-9-yl)benzonitrile (1112197-04-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In ethanol; water; toluene; Inert atmosphere; Reflux;

DOI:10.1002/chem.200801355

Reference yield:

2-(9-anthryl)benzaldehyde → 2-(anthracen-9-yl)benzonitrile (1112197-04-2)

Guidance literature:

With hydroxylamine hydrochloride; In dimethyl sulfoxide; at 100 ℃; for 3h;

DOI:10.1021/ol301583y

Reference yield:

anthracene-9-boronic acid (100622-34-2) → 2-(anthracen-9-yl)benzonitrile (1112197-04-2)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,2-dimethoxyethane; ethanol; water / Inert atmosphere; Reflux

2: hydroxylamine hydrochloride / dimethyl sulfoxide / 3 h / 100 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydroxylamine hydrochloride; sodium carbonate; In 1,2-dimethoxyethane; ethanol; water; dimethyl sulfoxide; 1: Suzuki-Miyaura cross coupling reaction;

DOI:10.1021/ol301583y

upstream raw materials:

9,10-Dibromoanthracene

2-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-benzonitrile

anthracene-9-boronic acid

ortho-bromobenzaldehyde

Downstream raw materials:

3'-(p-tolyl)-10H-spiro[anthracene-9,1'-isoindol]-10-one

Refernces

• 1、 Zehm, Daniel,Fudickar, Werner,Hans, Melanie,Schilde, Uwe,Kelling, Alexandra,Linker, Torsten. "9,10-diarylanthracenes as molecular switches: Syntheses, properties, isomerisations and their reactions with singlet oxygen". experimental part. p. 11429 - 11441. Retrieved 2009/12/03.