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

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

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.

The use of the arylhydrazine synthetic amino of the biphenyl method

The present invention describes a method for synthesising 2-aminobiphenyls and derivatives thereof. This method can be performed cost-effectively and is based on selective reactions. Functionalised biphenyl compounds are of great interest, particularly as pharmaceuticals and agricultural chemicals, and as precursors for such active ingredients. The method for producing a compound of formula 3 is characterised in that a compound of formula 1 is reacted with a compound of formula 2 in the presence of an oxidising agent.

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.