2,2'-Azonaphthalene

Base Information

• Chemical Name: 2,2'-Azonaphthalene
• CAS No.: 582-08-1
• Molecular Formula: C20H14N2
• Molecular Weight: 282.345
• European Community (EC) Number: 637-326-3
• NSC Number: 30976
• UNII: 38C4HK2J9M
• DSSTox Substance ID: DTXSID00871777
• Nikkaji Number: J54.467A
• Wikidata: Q27256772
• Mol file: 582-08-1.mol

Synonyms:2,2'-AZONAPHTHALENE;582-08-1;Diazene, di-2-naphthalenyl-;Di-beta-naphthyldiimide;NSC 30976;BRN 0959431;UNII-38C4HK2J9M;38C4HK2J9M;DI(NAPHTHALEN-2-YL)DIAZENE;NSC-30976;dinaphthalen-2-yldiazene;NSC30976;2,2'-Azobisnaphthalene;Di-.beta.-naphthyldiimide;2,2'-DIAZONAPHTHALENE;BIS(2-NAPHTHYL)DIAZENE;(E)-dinaphthalen-2-yl-diazene;SCHEMBL3283287;SCHEMBL10017620;DTXSID00871777;WLN: L66J CNUN- CL66J;1,2-DI-2-NAPHTHALENYLDIAZENE;AKOS024338378;LS-23480;DIAZENE, 1,2-DI-2-NAPHTHALENYL-;Q27256772

Chemical Property of 2,2'-Azonaphthalene

Chemical Property:

• Vapor Pressure: 4.51E-09mmHg at 25°C
• Melting Point: 208°C
• Refractive Index: 1.6450 (estimate)
• Boiling Point: 484.5°Cat760mmHg
• Flash Point: 239.8°C
• PSA: 24.72000
• Density: 1.12g/cm³
• LogP: 6.40840
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 282.115698455
• Heavy Atom Count: 22
• Complexity: 355

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C=C(C=CC2=C1)N=NC3=CC4=CC=CC=C4C=C3

Technology Process of 2,2'-Azonaphthalene

There total 15 articles about 2,2'-Azonaphthalene 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: 80.1%

1,2-di(naphthalen-2-yl)hydrazine (613-64-9) → 7H-dibenzo[c,g]carbazole (194-59-2) + 1,1'-binaphthalene-2,2'-diamine (4488-22-6,18531-95-8) + 2,2'-azonaphthalene (582-08-1)

Guidance literature:

With lithium perchlorate; perchloric acid; In 1,4-dioxane; water; at 0 ℃; for 24h;

DOI:10.1021/ja00297a030

Reference yield: 42.0%

2-azidonaphthalene (20937-86-4) → 2-nitronaphthalene (581-89-5) + 2-methoxynaphthylamine (2246-42-6) + 1-amino-2-chloronaphthalene (13711-39-2) + 2,2'-azonaphthalene (582-08-1)

Guidance literature:

With hydrogenchloride; In methanol; Further byproducts given; Irradiation; also in presence of 0.015M KCN/MeCN-H₂O;

Reference yield: 42.0%

methanol (67-56-1) + 2-azidonaphthalene (20937-86-4) → 2-nitronaphthalene (581-89-5) + 2-methoxynaphthylamine (2246-42-6) + dibenzo[a,h]phenazine (226-47-1) + 1-amino-2-chloronaphthalene (13711-39-2) + naphthalen-2-ylamine (91-59-8) + 2,2'-azonaphthalene (582-08-1)

Guidance literature:

With hydrogenchloride; Product distribution; Irradiation;

upstream raw materials:

1,2-di(naphthalen-2-yl)hydrazine

benzene

methanol

2-azidonaphthalene

Downstream raw materials:

1,1'-binaphthalene-2,2'-diamine

benzyl-2-naphthylamine

4,5-diphenyl-dinaphtho[2,1-e;1',2'-g][1,4]diazocine

naphthalen-2-ylamine

Refernces

• 1、 Shine, Henry J.,Gruszecka, Ewa,Subotkowski, Witold,Brownawell, Marilyn,Filippo, Joseph San, Jr.. "Heavy-Atom Kinetic Isotope Effects in the Acid-Catalysed and Thermal Rearrangements of 2,2'-Hydrazonaphthalene. Transition-State Differences in their Concerted Rearrangements". . p. 3218 - 3223. Retrieved 2007/10/02.
• 2、 Albini, Angelo,Bettinetti, Gian Franco,Fasani, Elisa,Pietra, Silvio. "PHOTOCHEMICAL DECOMPOSITION OF 2-AZIDOPHENAZINE IN ALCOHOLS AND IN THE PRESENCE OF CYANIDE ION". . p. 13 - 18. Retrieved 2007/10/02.