188731-34-2

Basic information

• Product Name: 4'-Chloro-5-fluoro-1,1'-biphenyl-2-amine
• Synonyms: 4'-Chloro-5-fluoro-1,1'-biphenyl-2-amine;2-Amino-4'-chloro-5-fluorobiphenyl;4'-Chloro-5-fluoro-[1,1'-biphenyl]-2-amine, 2-(4-Chlorophenyl)-4-fluoroaniline
• CAS NO: 188731-34-2
• Molecular Formula: C₁₂H₉ClFN
• Molecular Weight: 221.6579632
• Mol File: 188731-34-2.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4'-Chloro-5-fluoro-1,1'-biphenyl-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-Chloro-5-fluoro-1,1'-biphenyl-2-amine(188731-34-2)
• EPA Substance Registry System: 4'-Chloro-5-fluoro-1,1'-biphenyl-2-amine(188731-34-2)

Safety Data

• Hazardous Substances Data: 188731-34-2(Hazardous Substances Data)

Upstream product

• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 371-40-4 4-fluoroaniline 
• 106-47-8 4-chloro-aniline 
• 110213-25-7 C₆H₄ClN₂O^(1-)*Na⁽¹⁺⁾ 
• 71-43-2 benzene 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 2028-74-2 p-chlorobenzenediazonium chloride 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 62-53-3 aniline 

Relevant articles and documents

Regiospecific Introduction of Halogens on the 2-Aminobiphenyl Subunit Leading to Highly Potent and Selective M3 Muscarinic Acetylcholine Receptor Antagonists and Weak Inverse Agonists

Muscarinic M3 receptor antagonists and inverse agonists displaying high affinity and subtype selectivity over the antitarget M2 are valuable pharmacological tools and may enable improved treatment of chronic obstructive pulmonary disease (COPD), asthma, or urinary incontinence. On the basis of known M3 antagonists comprising a piperidine or quinuclidine unit attached to a biphenyl carbamate, 5-fluoro substitution was responsible for M3 subtype selectivity over M2, while 3′-chloro substitution substantially increased affinity through a σ-hole interaction. Resultantly, two piperidinyl-and two quinuclidinium-substituted biphenyl carbamates OFH243 (13n), OFH244 (13m), OFH3911 (14n), and OFH3912 (14m) were discovered, which display two-digit picomolar affinities with Ki values from 0.069 to 0.084 nM, as well as high selectivity over the M2 subtype (46-to 68-fold). While weak inverse agonistic properties were determined for the biphenyl carbamates 13m and 13n, neutral antagonism was observed for 14m and 14n and tiotropium under identical assay conditions.

Radical Arylation of Anilines and Pyrroles via Aryldiazotates

The radical arylation of anilines and pyrroles can be achieved under transition-metal- and catalyst-free conditions by using aryldiazotates in strongly alkaline aqueous solutions. The aryldiazotates act as protected diazonium ions, which do not undergo azo coupling with electron-rich aromatic substrates, but can still serve as an aryl radical source at slightly elevated temperatures. Based on an improved preparation of aryldiazotates in aqueous solution, homolytic aromatic substitutions of anilines and pyrroles were conducted with good overall yields and high regioselectivity. Moreover, DFT calculations provided further mechanistic insights.

Strongly Directing Substituents in the Radical Arylation of Substituted Benzenes

Although general interest in radical arylation reactions has grown rapidly in recent years, poor regioselectivities and the need to use a large excess of the radical-accepting arene have hindered their application to substituted benzenes. We now describe experimental and computational investigations into the substituent effects that lead to regioselective addition based on the recent discovery of anilines as outstanding substrates for radical arylations.