2,2'-Biphenyldiamine

Base Information

• Chemical Name: 2,2'-Biphenyldiamine
• CAS No.: 1454-80-4
• Molecular Formula: C12H12N2
• Molecular Weight: 184.241
• Hs Code.: 2921590090
• European Community (EC) Number: 685-728-2
• NSC Number: 99367
• UNII: 0DJ0J26MNW
• DSSTox Substance ID: DTXSID00163003
• Nikkaji Number: J7.495K
• Wikidata: Q83031834
• ChEMBL ID: CHEMBL1384563
• Mol file: 1454-80-4.mol

Synonyms:1454-80-4;2,2'-BIPHENYLDIAMINE;2,2'-Diaminobiphenyl;[1,1'-Biphenyl]-2,2'-diamine;o-Benzidine;Biphenyl-2,2'-diamine;o,o'-Diaminobiphenyl;2,2'-Diaminodiphenyl;2-(2-aminophenyl)aniline;1,1'-Biphenyl-2,2'-diamine;2,2/'-Biphenyldiamine;(1,1'-Biphenyl)-2,2'-diamine;NSC 99367;BRN 1949579;0DJ0J26MNW;MFCD00034060;NSC-99367;4-13-00-00356 (Beilstein Handbook Reference);NSC99367;Enamine_000878;UNII-0DJ0J26MNW;NCIOpen2_002089;MLS000765308;SCHEMBL169281;2,2'-diamino-1,1'-biphenyl;CHEMBL1384563;DTXSID00163003;HMS1396H20;HMS2620M18;AKOS000269002;NCGC00245148-01;2'-Amino[1,1'-biphenyl]-2-ylamine #;LS-03557;LS-44287;SMR000289413;2,2'-Biphenyldiamine, >=96.5% (GC);CS-0196799;D5255;FT-0609157;T70293;AE-641/02339059;Z56786620

Chemical Property of 2,2'-Biphenyldiamine

Chemical Property:

• Melting Point: 76.0 to 80.0 °C
• Refractive Index: 1.6266 (estimate)
• Boiling Point: 352.5 °C at 760 mmHg
• PKA: 3.70±0.10(Predicted)
• Flash Point: 198.9 °C
• PSA: 52.04000
• Density: 1.156 g/cm³
• LogP: 3.68040
• Solubility.: soluble in Methanol
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 184.100048391
• Heavy Atom Count: 14
• Complexity: 161

Purity/Quality:

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

2,2'-Diaminobiphenyl >99.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 22-41-50
• Safety Statements: 26-39-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C2=CC=CC=C2N)N
• Uses: 2,2''-Biphenyldiamine is a good starting material in the synthesis of carbazole and carbazole derivatives.

Technology Process of 2,2'-Biphenyldiamine

There total 59 articles about 2,2'-Biphenyldiamine 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: 50.0%

1-nitro-2-(2-nitrophenyl)benzene (2436-96-6) → benzo[c]cinnoline (230-17-1) + 1,1'-biphenyl-2,2'-diamine (1454-80-4)

Guidance literature:

With isopropyl alcohol; for 24h; UV-irradiation; Green chemistry;

DOI:10.1039/c5cc02713f

Reference yield: 35.0%

2-iodophenylamine (615-43-0) + 2-nitrophenylboronic acid (5570-19-4) → 1-nitro-2-(2-nitrophenyl)benzene (2436-96-6) + 1,1'-biphenyl-2,2'-diamine (1454-80-4) + 2-amino-2'-nitrobiphenyl (35883-86-4)

Guidance literature:

With potassium dihydrogenphosphate; tetrabutylammomium bromide; palladium diacetate; In water; N,N-dimethyl-formamide; at 100 ℃; for 48h;

DOI:10.1021/jo051589t

Reference yield: 23.0%

2-azido-2'-biphenylylamine (54147-64-7) → benzo[c]cinnoline (230-17-1) + 4-aminocarbazole (18992-64-8) + 1,1'-biphenyl-2,2'-diamine (1454-80-4)

Guidance literature:

In methanol; for 0.75h; Ambient temperature; Irradiation;

DOI:10.1246/bcsj.67.895

upstream raw materials:

1-nitro-2-(2-nitrophenyl)benzene

[1,1'-biphenyl]-2,2'-dicarboxamide

2-Chloronitrobenzene

biphenyl

Downstream raw materials:

N,N'-biphenyl-2,2'-diyl-bis-trans-cinnamamide

N,N'-biphenyl-2,2'-diyl-bis-phthalamic acid

N,N'-bis-(2,4-dinitro-phenyl)-biphenyl-2,2'-diyldiamine

6-(4-nitro-phenyl)-5H-dibenzo[d,f][1,3]diazepine

Refernces

• 1、 Kaur, Jaspreet,Pal, Bonamali. "Selective formation of benzo[c]cinnoline by photocatalytic reduction of 2,2′-dinitrobiphenyl using TiO2 and under UV light irradiation". . p. 8500 - 8503. Retrieved 2015.
• 2、 Radell et al.. "-". . p. 1051. Retrieved 1956.
• 3、 Proctor, C. J.,Kralj, B.,Larka, E. A.,Porter, C. J.,Maquestiau, A.,Beynon, J. H.. "Studies of Consecutive Reactions of Quinones in a Reversed Geometry Mass Spectrometer". . p. 312 - 322. Retrieved 1981.
• 4、 Shin, Un Chul,Jung, Ki-Hye,Park, Ji-Ae,Lee, Ji Woong,Kim, Jung Young,Seo, Jongbum,Lee, Kyo Chul,Choi, Jae Yong. "Synthesis and Preliminary Evaluation of 68Ga-NOTA-Biphenyl-c(RGDyK) for the Quantification of Integrin αvβ3". . p. 1415 - 1418. Retrieved 2017.
• 5、 Corbett,Holt. "-". . p. 3646,3651. Retrieved 1960.
• 6、 Farnum,Rasheed. "". . p. 573,574. Retrieved 1977.
• 7、 Scarborough, Christopher C.,Grady, Michael J. W.,Guzei, Ilia A.,Gandhi, Bhavesh A.,Bunel, Emilio E.,Stahl, Shannon S.. "PdII complexes possessing a seven-membered N-heterocyclic carbene ligand". . p. 5269 - 5272. Retrieved 2005.
• 8、 Jung, Ki-Hye,Kim, Hee-Kyung,Lee, Gang Ho,Kang, Duk-Sik,Park, Ji-Ae,Kim, Kyeong Min,Chang, Yongmin,Kim, Tae-Jeong. "Gd complexes of macrocyclic diethylenetriaminepentaacetic acid (DTPA) biphenyl-2,2′-bisamides as strong blood-pool magnetic resonance imaging contrast agents". . p. 5385 - 5394. Retrieved 2011.
• 9、 Toyama, Hirozumi,Nakamura, Masaharu,Hashimoto, Yuichi,Fujii, Shinya. "Design and synthesis of novel ROR inverse agonists with a dibenzosilole scaffold as a hydrophobic core structure". . p. 2982 - 2988. Retrieved 2015.
• 10、 Amirnasr, Mehdi,Kickelbick, Guido,Dehghanpour, Saeed. "Synthesis, characterization, and X-ray crystal structures of bis [N-(3,3-diphenylallylidene)quinolin-8-amine-κV,κN 8]copper(1+) tetraphenylborate(1-)". . p. 274 - 284. Retrieved 2006.