2,5-Difluoro-7,7,8,8-tetracyanoquinodimethane

Base Information

• Chemical Name: 2,5-Difluoro-7,7,8,8-tetracyanoquinodimethane
• CAS No.: 73318-02-2
• Molecular Formula: C12H2 F2 N4
• Molecular Weight: 240.171
• Hs Code.: 2926909090
• European Community (EC) Number: 680-182-1
• DSSTox Substance ID: DTXSID10413647
• Nikkaji Number: J658.361J
• Wikidata: Q82221922
• Mol file: 73318-02-2.mol

Synonyms:2,5-Difluoro-7,7,8,8-tetracyanoquinodimethane;73318-02-2;2-[4-(dicyanomethylidene)-2,5-difluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile;SCHEMBL258842;2,5-TCNQF2;DTXSID10413647;MFCD08276347;CS-0364963;D3200;D90153

Chemical Property of 2,5-Difluoro-7,7,8,8-tetracyanoquinodimethane

Chemical Property:

• Melting Point: 270 °C
• Boiling Point: 37.4oC at 760 mmHg
• PSA: 95.16000
• Density: 1.44g/cm3
• LogP: 0.36052
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 240.02475240
• Heavy Atom Count: 18
• Complexity: 639

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-[4-(Dicyanomethylidene)-2,5-difluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=C(C#N)C#N)C=C(C1=C(C#N)C#N)F)F

Technology Process of 2,5-Difluoro-7,7,8,8-tetracyanoquinodimethane

There total 3 articles about 2,5-Difluoro-7,7,8,8-tetracyanoquinodimethane 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: 73.0%

2,2′-(2,5-difluoro-1,4-phenylene)dimalononitrile → 2,5-difluoro-7,7,8,8-tetracyano-p-quinodimethane (73318-02-2)

Guidance literature:

With bromine; In water; at 20 ℃; for 48h;

DOI:10.1021/acs.joc.0c00053

Reference yield:

1,4-dibromo-2,5-difluorobenzene (327-51-5) → 2,5-difluoro-7,7,8,8-tetracyano-p-quinodimethane (73318-02-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere; Glovebox; Sealed tube

1.2: 16 h / Reflux; Inert atmosphere; Glovebox; Sealed tube

2.1: bis[(trimethylsilyl)methyl](1,5-cyclooctadiene)palladium(II); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium hydride / 1,4-dioxane / 24 h / 100 °C / Glovebox; Autoclave

3.1: bromine / water / 48 h / 20 °C

With bis[(trimethylsilyl)methyl](1,5-cyclooctadiene)palladium(II); bromine; sodium hydride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1021/acs.joc.0c00053

Reference yield:

2-(4-bromo-2,5-difluorophenyl)malononitrile → 2,5-difluoro-7,7,8,8-tetracyano-p-quinodimethane (73318-02-2)

Guidance literature:

Multi-step reaction with 2 steps

1: bis[(trimethylsilyl)methyl](1,5-cyclooctadiene)palladium(II); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium hydride / 1,4-dioxane / 24 h / 100 °C / Glovebox; Autoclave

2: bromine / water / 48 h / 20 °C

With bis[(trimethylsilyl)methyl](1,5-cyclooctadiene)palladium(II); bromine; sodium hydride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; water;

DOI:10.1021/acs.joc.0c00053

upstream raw materials:

1,4-dibromo-2,5-difluorobenzene

Downstream raw materials:

[Fe(C₅Me₄H)₂][2,5-F₂₍7,7,8,8-tetracyano-p-quinodimethanide)]

Refernces