p-Benzenedimalononitrile

Base Information

• Chemical Name: p-Benzenedimalononitrile
• CAS No.: 18643-56-6
• Molecular Formula: C12H6N4
• Molecular Weight: 206.206
• NSC Number: 105236
• DSSTox Substance ID: DTXSID80295735
• Nikkaji Number: J721.706D
• Wikidata: Q82035850
• Mol file: 18643-56-6.mol

Synonyms:p-Benzenedimalononitrile;18643-56-6;2,2'-(1,4-Phenylene)dimalononitrile;2-[4-(dicyanomethyl)phenyl]propanedinitrile;MFCD00455666;p-phenylenedimalononitrile;Tetracyano-p-xylene;NSC105236;SCHEMBL3151966;DTXSID80295735;AC8233;NSC-105236;SY263334;2,2?-(1,4-PHENYLENE)DIMALONONITRILE;2,2 inverted exclamation mark -(1,4-Phenylene)dimalononitrile

Chemical Property of p-Benzenedimalononitrile

Chemical Property:

• Boiling Point: 409.6°Cat760mmHg
• Flash Point: 203.5°C
• Density: 1.264g/cm³
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 206.059246208
• Heavy Atom Count: 16
• Complexity: 358

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(C#N)C#N)C(C#N)C#N

Technology Process of p-Benzenedimalononitrile

There total 25 articles about p-Benzenedimalononitrile 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: 98.0%

para-diiodobenzene (624-38-4,1032416-46-8) + malononitrile (109-77-3) → 2-(4-Dicyanomethyl-phenyl)-malononitrile (18643-56-6)

Guidance literature:

para-diiodobenzene; malononitrile; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 1h;

With 1,4-di(diphenylphosphino)-butane; palladium dichloride; In tetrahydrofuran; at 85 ℃; for 24h;

Reference yield: 95.0%

1.4-dibromobenzene (106-37-6) + malononitrile (109-77-3) → 2-(4-Dicyanomethyl-phenyl)-malononitrile (18643-56-6)

Guidance literature:

1.4-dibromobenzene; malononitrile; With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 2h;

With triphenylphosphine; palladium dichloride; In 1-methyl-pyrrolidin-2-one; at 125 ℃; for 10h; Reagent/catalyst; Solvent; Temperature;

Reference yield: 90.0%

para-dichlorobenzene (106-46-7,84348-21-0) + malononitrile (109-77-3) → 2-(4-Dicyanomethyl-phenyl)-malononitrile (18643-56-6)

Guidance literature:

para-dichlorobenzene; malononitrile; With caesium carbonate; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 4h;

With triphenylphosphine; palladium dichloride; In 1-methyl-pyrrolidin-2-one; at 125 ℃; for 20h;

upstream raw materials:

7,7',8,8'-tetracyanoquinodimethane

9H-fluorene

2,3-dimethylnaphthalene

Hexamethylbenzene

Downstream raw materials:

tetrathiafulvalene 7,7,8,8-tetracyanoquinodimethane salt

7,7',8,8'-tetracyanoquinodimethane

1,4-di(1,1-dicyanoethyl)benzene

2-(4-Dicyanomethyl-phenyl)-2-(2-oxo-propyl)-malononitrile

Refernces

• 1、 Szablewski, Marek,Thomas, Philip R.,Thornton, Anna,Bloor, David,Cross, Graham H.,Cole, Jacqueline M.,Howard, Judith A. K.,Malagoli, Massimo,Meyers, Fabienne,Brédas, Jean-Luc,Wenseleers, Wim,Goovaerts, Etienne. "Highly dipolar, optically nonlinear adducts of tetracyano-p-quinodimethane: Synthesis, physical characterization, and theoretical aspects". . p. 3144 - 3154. Retrieved 1997.
• 2、 -. "Bis (1 - aryl - 4H - pyrazole) structured organic pigment and preparation method thereof". Paragraph 0051-0052. . Retrieved 2021/11/27.