1,1'-biphenyl-3,3'-diamine

Base Information

• Chemical Name: 1,1'-biphenyl-3,3'-diamine
• CAS No.: 2050-89-7
• Molecular Formula: C12H12 N2
• Molecular Weight: 184.241
• Hs Code.: 2921590090
• Mol file: 2050-89-7.mol

Synonyms:3,3'-Biphenyldiamine(7CI,8CI); 3,3'-Diaminobiphenyl; 3,3'-Diaminodiphenyl

Chemical Property of 1,1'-biphenyl-3,3'-diamine

Chemical Property:

• Melting Point: 93.5°C
• Refractive Index: 1.6266 (estimate)
• Boiling Point: 427.8°Cat760mmHg
• PKA: 4.72±0.10(Predicted)
• Flash Point: 254.6°C
• PSA: 52.04000
• Density: 1.156g/cm³
• LogP: 3.68040
• Water Solubility.: 11g/L(100 oC)

Purity/Quality:

98%min ^*data from raw suppliers

1,1'-Biphenyl-3,3'-diamine dihydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,1'-biphenyl-3,3'-diamine

There total 4 articles about 1,1'-biphenyl-3,3'-diamine 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: 88.0%

1-bromocyclohexane (108-85-0) + m-bistrimethylsilylaminophenylmagnesium bromide → 3,3'-diaminobiphenyl (2050-89-7) + 3-cyclohexylbenzenamine (5369-21-1)

Guidance literature:

1-bromocyclohexane; [Fe(C₂H₄)4][Li(tmeda)]2; In tetrahydrofuran;

m-bistrimethylsilylaminophenylmagnesium bromide; In tetrahydrofuran; diethyl ether; at 0 ℃; for 1.5h; Further stages.;

DOI:10.1021/ja801466t

Reference yield: 44.0%

3-Aminophenylboronic acid (30418-59-8,280563-63-5) → 3-biphenyl amine (2243-47-2) + 3,3'-diaminobiphenyl (2050-89-7) + m-Hydroxyaniline (591-27-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; for 20h; Heating;

DOI:10.1021/jo982210o

Reference yield:

p-toluidine (106-49-0,12221-03-3) + (3-(bis(trimethylsilyl)amino)phenyl)magnesium bromide → 3,3'-diaminobiphenyl (2050-89-7) + N1-(p-tolyl)benzene-1,3-diamine

Guidance literature:

p-toluidine; With n-butyllithium; dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 0.5h; Inert atmosphere; Schlenk technique;

(3-(bis(trimethylsilyl)amino)phenyl)magnesium bromide; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; bis(acetylacetonate)nickel(II); 1,2-dichloro-2-methylpropane; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 3h; Inert atmosphere; Schlenk technique;

With hydrogenchloride; In tetrahydrofuran; hexane; water; ethyl acetate; for 0.166667h; Inert atmosphere; Schlenk technique;

DOI:10.1021/ol302688u

upstream raw materials:

3-Aminophenylboronic acid

3-chloro-aniline

1-bromocyclohexane

p-toluidine

Downstream raw materials:

N³,N³,N^3',N^3'-Tetrakis-(4-methoxy-phenyl)-biphenyl-3,3'-diamine

Pyridine-2,5-dicarboxylic acid

C₄₈H₃₈N₄

3,3'-dibromobiphenyl

Refernces

• 1、 Ilies, Laurean,Matsubara, Tatsuaki,Nakamura, Eiichi. "Nickel-catalyzed synthesis of diarylamines via oxidatively induced C-N bond formation at room temperature". supporting information. p. 5570 - 5573,4. Retrieved 2012/12/12.