Naphthalene-1,4-dicarbonitrile

Base Information

• Chemical Name: Naphthalene-1,4-dicarbonitrile
• CAS No.: 3029-30-9
• Molecular Formula: C12H6N2
• Molecular Weight: 178.193
• Hs Code.: 2926909090
• European Community (EC) Number: 221-197-1
• NSC Number: 128542
• UNII: HP6DS2Q5U8
• DSSTox Substance ID: DTXSID00184374
• Nikkaji Number: J205.334I
• Wikidata: Q72493445
• Mol file: 3029-30-9.mol

Synonyms:Naphthalene-1,4-dicarbonitrile;3029-30-9;1,4-Dicyanonaphthalene;1,4-Naphthalenedicarbonitrile;HP6DS2Q5U8;EINECS 221-197-1;NSC-128542;NSC128542;UNII-HP6DS2Q5U8;ghl.PD_Mitscher_leg0.246;SCHEMBL151936;DTXSID00184374;C12-H6-N2;MFCD03093626;AKOS022505305;NSC 128542;CS-0142193;D2758;FT-0766693

Chemical Property of Naphthalene-1,4-dicarbonitrile

Chemical Property:

• Vapor Pressure: 1.21E-06mmHg at 25°C
• Melting Point: 209-211°C
• Refractive Index: 1.663
• Boiling Point: 401.2 °C at 760 mmHg
• Flash Point: 205 °C
• PSA: 47.58000
• Density: 1.23g/cm³
• LogP: 2.58316
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 178.053098200
• Heavy Atom Count: 14
• Complexity: 271

Purity/Quality:

99.9% ^*data from raw suppliers

1,4-Dicyanonaphthalene ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22-36/37/38
• Safety Statements: 22-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=CC=C(C2=C1)C#N)C#N
• Uses: 1,4-Dicyanonaphthalene is used in biological studies as electron transfer mechanism of nucleic acid precursors and ctDNA with protein enzymes and several fluorescence probes in both static and excited states.

Technology Process of Naphthalene-1,4-dicarbonitrile

There total 40 articles about Naphthalene-1,4-dicarbonitrile 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: 96.0%

C12H10N2S2 → naphthalene-1,4-dicarbonitrile (3029-30-9)

Guidance literature:

With triphenyl bismuth ⁽²⁺⁾; dichloride; triethylamine; In dichloromethane; at 20 ℃; for 0.25h;

DOI:10.1002/ejoc.201900563

Reference yield: 82.0%

1,4-di-tert-butyl-1,4-diazabutadiene (28227-42-1,30834-74-3) + 1,2-phenylenediacetonitrile (613-73-0) → naphthalene-1,4-dicarbonitrile (3029-30-9) + tert-butylamine (75-64-9)

Guidance literature:

In dimethyl sulfoxide; at 120 ℃; for 1h;

Reference yield: 78.0%

1,4-dibromonaphthalene (83-53-4) → naphthalene-1,4-dicarbonitrile (3029-30-9)

Guidance literature:

With [bmim]BF₄; sodium carbonate; N,N`-dimethylethylenediamine; palladium dichloride; for 0.566667h; microwave irradiation;

DOI:10.1055/s-2006-947364

upstream raw materials:

syn-1,2:3,4-naphthalene dioxide

potassium cyanide

1,4-dibromonaphthalene

copper(I) cyanide

Downstream raw materials:

naphthalene-1,4-dicarboxylic acid

[4-(1,4-Dicyano-1,2-dihydro-naphthalen-1-ylmethyl)-phenyl]-acetic acid methyl ester

1-Benzyl-1,2-dihydro-1,4-naphthalenedicarbonitrile

1,1'-(1,2-ethanediyl)bisbenzene

Refernces

• 1、 Gopi, Elumalai,Gravel, Edmond,Doris, Eric. "Triphenylbismuth Dichloride-Mediated Conversion of Thioamides to Nitriles". supporting information. p. 4043 - 4045. Retrieved 2019/06/24.
• 2、 -. "Corresponding amine nitrile and method of manufacturing thereof". . . Retrieved 2018/05/24.