2-(Dimethylamino)-2'-bromo-1,1'-biphenyl

Base Information

• Chemical Name: 2-(Dimethylamino)-2'-bromo-1,1'-biphenyl
• CAS No.: 213697-67-7
• Molecular Formula: C14H14BrN
• Molecular Weight: 276.17166
• Hs Code.: 2921499090
• European Community (EC) Number: 621-916-2
• DSSTox Substance ID: DTXSID10584563
• Wikidata: Q82476241
• Mol file: 213697-67-7.mol

Synonyms:213697-67-7;2-(Dimethylamino)-2'-bromo-1,1'-biphenyl;2-(2-bromophenyl)-N,N-dimethylaniline;2'-Bromo-N,N-dimethyl-[1,1'-biphenyl]-2-amine;SCHEMBL413186;DTXSID10584563;AKOS004116284;2-(2-bromophenyl)-N,N-dimethyl-aniline;2'-Bromo-N,N-dimethyl[1,1'-biphenyl]-2-amine;A815298;2-(Dimethylamino)-2'-bromo-1,1'-biphenyl, 97%;J-014014

Chemical Property of 2-(Dimethylamino)-2'-bromo-1,1'-biphenyl

Chemical Property:

• Melting Point: 58-64 °C
• Boiling Point: 350.987 °C at 760 mmHg
• PKA: 4.70±0.18(Predicted)
• Flash Point: 166.072 °C
• PSA: 3.24000
• Density: 1.322 g/cm³
• LogP: 4.18210
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 275.03096
• Heavy Atom Count: 16
• Complexity: 217

Purity/Quality:

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

2-(DIMETHYLAMINO)-2'-BROMO-1,1'-BIPHENYL 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 22-36-50/53
• Safety Statements: 26-36-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C)C1=CC=CC=C1C2=CC=CC=C2Br

Technology Process of 2-(Dimethylamino)-2'-bromo-1,1'-biphenyl

There total 5 articles about 2-(Dimethylamino)-2'-bromo-1,1'-biphenyl 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: 91.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2'-bromo-N-methyl-[1,1'-biphenyl]-2-amine (73006-87-8) → 2'-bromo-N,N-dimethyl-[1,1'-biphenyl]-2-amine (213697-67-7)

Guidance literature:

With formic acid; at 100 ℃;

DOI:10.1039/d0cc01766c

Reference yield: 65.0%

1-Bromo-2-iodobenzene (583-55-1) + 2-(N,N-dimethylamino)phenylboronic acid (89291-23-6) → 2'-bromo-N,N-dimethyl-[1,1'-biphenyl]-2-amine (213697-67-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,2-dimethoxyethane; water; at 110 ℃; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2010.02.014

Reference yield: 35.0%

2-bromo-N,N-dimethylaniline (698-00-0) + 2,3-dibromobenzene (583-53-9) → 2'-bromo-N,N-dimethyl-[1,1'-biphenyl]-2-amine (213697-67-7)

Guidance literature:

2-bromo-N,N-dimethylaniline; With n-butyllithium; In hexane; at -78 ℃; for 1h; Inert atmosphere;

2,3-dibromobenzene; In hexane; for 2h; Inert atmosphere; Reflux;

DOI:10.1021/acs.orglett.7b01524

upstream raw materials:

1-Bromo-2-iodobenzene

2-(N,N-dimethylamino)phenylboronic acid

2-bromo-N,N-dimethylaniline

2,3-dibromobenzene

Downstream raw materials:

2-dimesitylboryl-2'-(N,N-dimethylamino)biphenyl

2'-(di-tert-butylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine

Refernces

• 1、 Muriel, Bastian,Orcel, Ugo,Waser, Jerome. "Palladium-Catalyzed Carboamination of Allylic Alcohols Using a Trifluoroacetaldehyde-Derived Tether". supporting information. p. 3548 - 3551. Retrieved 2017/07/17.
• 2、 Bonnaventure, Isabelle,Charette, Andre B.. "Probing the importance of the hemilabile site of bis(phosphine) monoxide ligands in the copper-catalyzed addition of diethylzinc to N-phosphinoylimines: Discovery of new effective chiral ligands". . p. 6330 - 6340. Retrieved 2008/12/22.