4,5-Dibromophthalonitrile

Base Information

• Chemical Name: 4,5-Dibromophthalonitrile
• CAS No.: 86938-64-9
• Molecular Formula: C8H2Br2N2
• Molecular Weight: 285.925
• DSSTox Substance ID: DTXSID30571531
• Nikkaji Number: J949.337I
• Wikidata: Q82459629
• Mol file: 86938-64-9.mol

Synonyms:4,5-dibromophthalonitrile;86938-64-9;4,5-Dibromobenzene-1,2-dicarbonitrile;1,2-Benzenedicarbonitrile, 4,5-dibromo-;MFCD22042793;SCHEMBL7046343;DTXSID30571531;AC7023;AKOS028113916;AS-78567;SY247549

Chemical Property of 4,5-Dibromophthalonitrile

Chemical Property:

• Boiling Point: 349.2±42.0 °C(Predicted)
• PSA: 47.58000
• Density: 2.09±0.1 g/cm3(Predicted)
• LogP: 2.95496
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 285.85642
• Heavy Atom Count: 12
• Complexity: 231

Purity/Quality:

99% ^*data from raw suppliers

4,5-Dibromophthalonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=CC(=C1Br)Br)C#N)C#N

Technology Process of 4,5-Dibromophthalonitrile

There total 3 articles about 4,5-Dibromophthalonitrile 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: 65.0%

zinc(II) cyanide (557-21-1) + 1,2-dibromo-4,5-diiodobenzene (529502-50-9) → 4,5-dibromobenzene-1,2-dicarbonitrile (86938-64-9)

Guidance literature:

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 120 ℃; for 60h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/jo802078f

Reference yield: 20.0%

potassium cyanide + 1,2-dibromo-4,5-diiodobenzene (529502-50-9) → 4,5-dibromo-2-iodobenzonitrile (1093683-51-2) + 4,5-dibromobenzene-1,2-dicarbonitrile (86938-64-9)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 70 ℃; for 72h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/jo802078f

Reference yield: 6.7%

phthalonitrile (91-15-6) → 4-bromo-1,2-dicyanobenzene (70484-01-4) + 4,5-dibromobenzene-1,2-dicarbonitrile (86938-64-9) + 3,6-dibromophthalodinitrile

Guidance literature:

With sulfuric acid; dibromoisocyanuric acid;

DOI:10.1016/S1386-1425(97)00236-9

upstream raw materials:

phthalonitrile

zinc(II) cyanide

1,2-dibromo-4,5-diiodobenzene

Downstream raw materials:

5,6-dibromo-1,3-diiminoisoindoline

4,5-bis(tert-butyldimethylsilylethynyl)phthalonitrile

Refernces

• 1、 Jurí?ek, Michal,Kouwer, Paul H. J.,Rehák, Juraj,Sly, Joseph,Rowan, Alan E.. "A novel modular approach to triazole-functionalized phthalocyanines using click chemistry". supporting information; experimental part. p. 21 - 25. Retrieved 2009/04/07.