Bisbenzimidazo[2,1-b:1',2'-j]benzo[lmn][3,8]phenanthroline-6,9-dione

Base Information

• Chemical Name: Bisbenzimidazo[2,1-b:1',2'-j]benzo[lmn][3,8]phenanthroline-6,9-dione
• CAS No.: 4216-02-8
• Deprecated CAS: 11098-10-5,156841-35-9,71838-92-1,633300-78-4,156841-35-9,633300-78-4,71838-92-1
• Molecular Formula: C26H12N4O2
• Molecular Weight: 412.407
• European Community (EC) Number: 224-152-4
• DSSTox Substance ID: DTXSID5063360
• Nikkaji Number: J93.158F
• Wikidata: Q72516201
• Mol file: 4216-02-8.mol

Synonyms:Vat Red 15;4216-02-8;Vat Red15;bisbenzimidazo[2,1-b:1',2'-j]benzo[lmn][3,8]phenanthroline-6,9-dione;EINECS 224-152-4;benzo[lmn]benzo[4,5]imidazo[2,1-b]benzo[4,5]imidazo[1,2-j][3,8]phenanthroline-6,9-dione;3,10,17,24-tetrazaoctacyclo[13.13.2.02,10.04,9.012,29.017,25.018,23.026,30]triaconta-1(29),2,4,6,8,12,14,18,20,22,24,26(30),27-tridecaene-11,16-dione;Bisbenzimidazo(2,1-b:1',2'-j)benzo(lmn)(3,8)phenanthroline-6,9-dione;3,10,17,24-tetraazaoctacyclo[13.13.2.0^{2,10}.0^{4,9}.0^{12,29}.0^{17,25}.0^{18,23}.0^{26,30}]triaconta-1(28),2,4(9),5,7,12,14,18(23),19,21,24,26,29-tridecaene-11,16-dione;C.I. Vat Red 15;cis-perinone;Algol Bordeaux RR;SCHEMBL824450;DTXSID5063360;STK874292;AKOS000513781;C.I.71100;LS-185218;C.I. 71100;W-106278;W-110241;F0020-1976;dibenzimidazo[2,1-b:1,2-j]benzo[lmn][3,8]phenanthroline-6,9-dione

Chemical Property of Bisbenzimidazo[2,1-b:1',2'-j]benzo[lmn][3,8]phenanthroline-6,9-dione

Chemical Property:

• Appearance/Colour: powder
• Vapor Pressure: 1.05E-33mmHg at 25°C
• Melting Point: 490-492 °C
• Refractive Index: 1.924
• Boiling Point: 906.7 °C at 760 mmHg
• PKA: 1.40±0.20(Predicted)
• Flash Point: 502.2 °C
• PSA: 68.74000
• Density: 1.66 g/cm³
• LogP: 4.34400
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 412.09602564
• Heavy Atom Count: 32
• Complexity: 780

Purity/Quality:

99.9% ^*data from raw suppliers

VAT RED 15 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)N=C3N2C(=O)C4=CC=C5C6=C(C=CC3=C46)C7=NC8=CC=CC=C8N7C5=O

Technology Process of Bisbenzimidazo[2,1-b:1',2'-j]benzo[lmn][3,8]phenanthroline-6,9-dione

There total 6 articles about Bisbenzimidazo[2,1-b:1',2'-j]benzo[lmn][3,8]phenanthroline-6,9-dione 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:

1,4,5,8-naphthalenetetracarboxylic dianhydride (81-30-1) + 1,2-diamino-benzene (95-54-5) → 1,4,5,8-naphthalene tetracarboxylic bis(benzimidazole) + benzo[lmn]benzo[4,5]imidazo[2,1-b]benzo[4,5]imidazo[1,2-j][3,8]phenanthroline-6,9-dione (4216-02-8)

Guidance literature:

With tin(II) chloride dihdyrate; zinc diacetate; propionic acid; for 8h; Inert atmosphere; Reflux;

DOI:10.1016/j.tetlet.2013.04.030

Reference yield:

1,4,5,8-naphthalenetetracarboxylic dianhydride (81-30-1) + 1,2-diamino-benzene (95-54-5) + naphthalene-1,8-diamine (479-27-6) → benzo[lmn]diperimidino[2,1-b:1',2'-j][3,8]phenanthroline-5,8-dione (20749-67-1) + benzo[lmn]benzo[4,5]imidazo[2,1-b]perimidino[1,2-j][3,8]phenanthroline-8,11-dione (4691-73-0) + benzo[lmn]diperimidino[2,1-b:2',1'-i][3,8]phenanthroline-7,18-dione (4578-87-4) + C30H14N4O2 + benzo[lmn]benzo[4,5]imidazo[2,1-b]benzo[4,5]imidazo[1,2-j][3,8]phenanthroline-6,9-dione (4216-02-8) + pigment orange 43 (4424-06-0,104432-60-2,136298-09-4,156841-34-8,42612-21-5,67053-85-4,79586-96-2)

Guidance literature:

With 70% by weight of the total weight of polyester; at 110 - 220 ℃; for 1h; Inert atmosphere;

Reference yield:

1,4,5,8-naphthalenetetracarboxylic dianhydride (81-30-1) + 1,2-diamino-benzene (95-54-5) → benzo[lmn]benzo[4,5]imidazo[2,1-b]benzo[4,5]imidazo[1,2-j][3,8]phenanthroline-6,9-dione (4216-02-8) + pigment orange 43 (4424-06-0,104432-60-2,136298-09-4,156841-34-8,42612-21-5,67053-85-4,79586-96-2)

Guidance literature:

With zinc diacetate; at 250 ℃; for 3h; Neat (no solvent);

DOI:10.1021/ol201973w

upstream raw materials:

1,4,5,8-naphthalenetetracarboxylic dianhydride

1,2-diamino-benzene

naphthalene-1,8-diamine

Refernces

• 1、 Taublaender, M. Josef,Gl?cklhofer, Florian,Marchetti-Deschmann, Martina,Unterlass, Miriam M.. "Green and Rapid Hydrothermal Crystallization and Synthesis of Fully Conjugated Aromatic Compounds". supporting information. p. 12270 - 12274. Retrieved 2018/08/01.
• 2、 Mamada, Masashi,Perez-Bolivar, Cesar,Anzenbacher, Pavel. "Green synthesis of polycyclic benzimidazole derivatives and organic semiconductors". supporting information; experimental part. p. 4882 - 4885. Retrieved 2011/12/05.