1203-43-6

Usage

Uses

Used in Pharmaceutical Research:
[1,1'-Biphenyl]-2-amine, 2'-chlorois utilized as a key intermediate in the development of novel drugs. Its unique structure and reactivity contribute to the design and synthesis of new pharmaceutical agents, potentially leading to breakthroughs in various therapeutic areas.
Used in Organic Synthesis:
In the field of organic synthesis, [1,1'-Biphenyl]-2-chloroserves as a fundamental building block for constructing more intricate organic molecules. The chlorine atom at the 2' position provides specific reactivity, allowing for a range of chemical reactions that can be harnessed to create diverse and complex molecular structures.
Used in Chemical Reactions:
[1,1'-Biphenyl]-2-amine, 2'-chloro-'s chlorine atom confers particular properties to [1,1'-Biphenyl]-2-amine, 2'-chloro-, making it a useful participant in various chemical reactions. This feature enhances its applicability in the synthesis of a wide array of organic compounds, further solidifying its importance in organic chemistry.

Upstream product

• 100-65-2 N-Phenylhydroxylamine 
• 108-90-7 chlorobenzene 
• 100-63-0 phenylhydrazine 
• 62-53-3 aniline 
• 10449-07-7 (2-chlorophenyl)hydrazine 
• 95-51-2 o-chloroaniline 

Downstream Products

• 14498-95-4 2'-chloro-[1,1'-biphenyl]-2-carboxylic acid 
• 76838-49-8 1-Benzoyl-3-(2'-chloro-biphenyl-2-yl)-thiourea 
• 107208-70-8 2-bromo-2’-chloro-1,1’-biphenyl 
• 3652-88-8 4-chloro-9H-carbazole 
• 1150-62-5 N-phenylcarbazole 
• 86-74-8 9H-carbazole 
• 90-41-5 2-phenylaniline 

Relevant academic research and scientific papers

Reaction of phenylhydrazines with arenes in the presence of aluminium trichloride

Phenylnitrenium ions are generated from phenylhydrazines by treatment with AlCl3. Reaction of a phenylnitrenium ion with arenes results in both aromatic N-substitution and C-substitution. In contrast, an N-methylphenylnitrenium ion undergoes exclusively aromatic C-substitution. Reaction of a phenylnitrenium ion with arenes present only in slight excess produces anilinated products in moderate to good yields.

Regioselective radical arylation of anilines with arylhydrazines

Substituted 2-aminobiphenyls have been prepared from arylhydrazines and anilines via radical arylation reactions under simple oxidative conditions. The strong directing effect of the free and unprotonated amino functionality leads to high regioselectivities, and anilines have been shown to be significantly better aryl radical acceptors than nitrobenzenes or phenyl ethers. The methodology is also applicable to phenols, which react best as phenolates under strongly basic conditions. Finally, radical arylation reactions of anilines and anilinium salts under various conditions have for the first time demonstrated that regioselectivity can also be controlled through the rearomatization step and that the addition of an aryl radical to a substituted benzene might even be reversible.

N- and C-attacks on aromatics of phenylnitrenium ion generated from N-phenylhydroxylamine in the presence of trifluoroacetic acid containing polyphosphoric acid or trifluoroacetic anhydride

A phenylnitrenium ion formed from N-phenylhydroxylamine in the presence of trifluoroacetic acid (TFA) containing polyphosphoric acid (PPA) interacts with the counterion -O2CCF3 and the unshared electron-pair of H2O, showing Hammett's ρ values -5.2 and -4.0 for N- and C-attacks on aromatics PhX (X = H, Me, Et, Ph and Cl), respectively. The ratio N-/C-attack for this nitrenium ion is lower than for the nitrenium ion interacting with only the counterion; the latter nitrenium ion is generated by the use of trifluoroacetic anhydride (TFAA) instead of PPA or by reaction of phenyl azide with aromatics in TFA. The ratio for the former nitrenium ion is affected by the aromatic substituent X:X = Me > X = Et > X = Ph > X = H > X = OMe at 20 and 50°C. The order for X = Cl is between those of X = H and X = Ph at 20°C, but highest at 50°C. The ratio is increased by higher reaction temperature and by decreased concentration of TFA. The results are demonstrated from the mechanistic viewpoint for the nitrenium ions.