4-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-benzonitrile

Base Information

• Chemical Name: 4-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-benzonitrile
• CAS No.: 15996-74-4
• Molecular Formula: C16H10N2O2
• Molecular Weight: 262.268
• Mol file: 15996-74-4.mol

Synonyms:4-phthalimidomethyl-benzonitrile;4-((1,3-DIOXOISOINDOLIN-2-YL)METHYL)BENZONITRILE;N-(4-cyanophenyl)methylphthalimide;N-(4-cyanobenzyl)phthalimide;4-Phthalimidomethyl-benzonitril;4-phthalimidomethylbenzonitrile;4-[(1,3-dioxo-2H-isoindol-2-yl)methyl]benzonitrile;

Chemical Property of 4-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-benzonitrile

Chemical Property:

• PSA: 61.17000
• LogP: 2.29238

Purity/Quality:

99% ^*data from raw suppliers

4-[(1,3-Dioxoisoindol-2-yl)methyl]benzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-benzonitrile

There total 12 articles about 4-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-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: 100.0%

potassium phtalimide (1074-82-4) + 4-cyanobenzyl bromide (17201-43-3) → 4-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]benzonitrile (15996-74-4)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; at 60 ℃; for 0.5h;

DOI:10.1002/jhet.5570400206

Reference yield: 93.0%

2-(4-methylthiobenzyl)isoindol-1,3-dione (247569-44-4) + 4-cyanobenzoic acid methyl ester (1129-35-7) → 4-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]benzonitrile (15996-74-4)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; 1,2-bis-(dicyclohexylphosphino)ethane; In o-xylene; at 140 ℃; for 24h; Glovebox; Inert atmosphere;

DOI:10.1021/jacs.1c00529

Reference yield: 90.0%

phthalic anhydride (85-44-9) + 4-aminobenzyl cyanide (10406-25-4) → 4-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]benzonitrile (15996-74-4)

Guidance literature:

With acetic acid; at 120 ℃; for 2h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.8b02287

upstream raw materials:

potassium phtalimide

4-cyanobenzyl chloride

4-cyanobenzyl bromide

phenyl formate

Downstream raw materials:

4-cyanobenzylamine hydrochloride

4-isothiocyanatomethyl-benzonitrile

N-benzyl-N'-(4-cyano-benzyl)-thiourea

4-((1,3-dioxoisoindolin-2-yl)methyl)benzothioamide

Refernces

• 1、 Delcaillau, Tristan,Boehm, Philip,Morandi, Bill. "Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers". supporting information. p. 3723 - 3728. Retrieved 2021/04/07.
• 2、 Wu, Xiaoyu,Ding, Guangni,Yang, Liqun,Lu, Wenkui,Li, Wanfang,Zhang, Zhaoguo,Xie, Xiaomin. "Alkoxide-Catalyzed Hydrosilylation of Cyclic Imides to Isoquinolines via Tandem Reduction and Rearrangement". supporting information. p. 5610 - 5613. Retrieved 2018/09/12.