263901-48-0

Basic information

• Product Name: 2'-METHOXY[1,1'-BIPHENYL]-4-AMINE
• Synonyms: TIMTEC-BB SBB010982;2'-METHOXY-BIPHENYL-4-YLAMINE;AKOS BAR-0138;(2'-methoxybiphenyl-4-yl)amine(SALTDATA: HCl);(2'-methoxybiphenyl-4-yl)amine 1HCl
• CAS NO: 263901-48-0
• Molecular Formula: C₁₃H₁₃NO
• Molecular Weight: 199.25
• Mol File: 263901-48-0.mol

Chemical Properties

• Boiling Point: 312.2 °C at 760 mmHg
• Flash Point: 143.4 °C
• Appearance: /
• Density: 1.1
• PKA: 4.37±0.10(Predicted)
• CAS DataBase Reference: 2'-METHOXY[1,1'-BIPHENYL]-4-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-METHOXY[1,1'-BIPHENYL]-4-AMINE(263901-48-0)
• EPA Substance Registry System: 2'-METHOXY[1,1'-BIPHENYL]-4-AMINE(263901-48-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 263901-48-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2'-Methoxy[1,1'-biphenyl]-4-amine is used as a reactant in the synthesis of 3-Hydroxypyrimidine-2,4-diones, which are selective RNase H inhibitors. These inhibitors play a crucial role in the development of antiviral and anticancer drugs, as they target the RNase H enzyme that is essential for the replication of certain viruses and cancer cells.
Used in Chemical Synthesis:
In the chemical industry, 2'-Methoxy[1,1'-biphenyl]-4-amine can be utilized as a building block for the synthesis of various complex organic molecules and pharmaceutical compounds. Its unique structure allows for further functionalization and modification, making it a versatile starting material for the development of new drugs and chemicals.

Upstream product

• 6460-91-9 2-methoxy-4'-nitrobiphenyl 
• 100-66-3 methoxybenzene 
• 100-65-2 N-Phenylhydroxylamine 
• 106-47-8 4-chloro-aniline 
• 5720-06-9 2-Methoxyphenylboronic acid 
• 540-37-4 p-aminoiodobenzene 
• 20281-20-3 4′-nitro-[1,1′-biphenyl]-2-ol 
• 3381-47-3 N-benzylidene-4-iodoaniline 
• 16750-63-3 2-methoxyphenylmagnesium bromide 
• 1243985-65-0 2-methoxyphenyl(triphenylphosphine)gold(I) 
• 106-40-1 4-bromo-aniline 
• 586-78-7 para-nitrophenyl bromide 

Downstream Products

• 666726-33-6 4-bromomethyl-6-(2-methoxybiphenyl)-2,2,-dimethyl-1,2-dihydroquinoline 
• 1025943-55-8 [3-(3-cyano-phenyl)-5-(2'-methoxy-biphenyl-4-ylcarbamoyl)-4,5-dihydro-isoxazol-5-yl]-acetic acid methyl ester 

Relevant articles and documents

3-Hydroxypyrimidine-2,4-diones as Selective Active Site Inhibitors of HIV Reverse Transcriptase-Associated RNase H: Design, Synthesis, and Biochemical Evaluations

Human immunodeficiency virus (HIV) reverse transcriptase (RT) associated ribonuclease H (RNase H) remains an unvalidated antiviral target. A major challenge of specifically targeting HIV RNase H arises from the general lack of selectivity over RT polymerase (pol) and integrase (IN) strand transfer (ST) inhibitions. We report herein the synthesis and biochemical evaluations of three novel 3-hydroxypyrimidine-2,4-dione (HPD) subtypes carefully designed to achieve selective RNase H inhibition. Biochemical studies showed the two subtypes with an N-1 methyl group (9 and 10) inhibited RNase H in low micromolar range without siginificantly inhibiting RT polymerase, whereas the N-1 unsubstituted subtype 11 inhibited RNase H in submicromolar range and RT polymerase in low micromolar range. Subtype 11 also exhibited substantially reduced inhibition in the HIV-1 INST assay and no significant cytotoxicity in the cell viability assay, suggesting that it may be amenable to further structure-activity relationship (SAR) for identifying RNase H inhibitors with antiviral activity.

Structure-activity relationship study of E6 as a novel necroptosis inducer

Necroptosis inducers represent a promising potential treatment for drug-resistant cancer. We herein describe the structure modification of E6, which was identified recently as a potent and selective necroptosis inducer. The studies described herein demonstrate for the first time that functionalized biphenyl derivatives possess necroptosis inducer activity. Furthermore, these studies have led to the identification of two promising compounds (5h and 5j) that can be used for further optimization studies as well as mechanism of action investigations.

Unified Protocol for Cobalt-Catalyzed Oxidative Assembly of Two Aryl Metal Reagents Using Oxygen as an Oxidant

The first cobalt-catalyzed oxidative cross-coupling reaction of two aryl metal reagents is described. An equivalent amount of two aryl Grignard or lithium reagents, after mediation by an equivalent amount of simple ClTi(OEt)3, was facilely assembled under the catalysis of 1 mol % of CoCl2/10 mol % of DMPU using oxygen. The cross-couplings between various aryl metal reagents, especially between two structurally similar aryl Grignard reagents, proceeded smoothly and selectively and, thus, provided a highly general and efficient method for the construction of biaryl compounds.

Organogold(I) phosphanes in palladium-catalyzed cross-coupling reactions in aqueous media

Cross-coupling reaction of organogold(I) phosphanes with organic electrophiles in aqueous media has been investigated. Reactions between isolated aryl-, alkenyl-, or alkynylgold(I) phosphanes and aryl halides or triflates, alkenyl halides, and allyl acetates proceed under palladium catalysis conditions at room temperature or 80 °C in water with THF as a co-solvent. The coupling reactions give good yields and are highly versatile and chemoselective, allowing the presence of free amino or hydroxy groups in the electrophile. This methodology was applied to the preparation of substituted phenylalanine esters in a demonstration that gold(I) organometallics are suitable reagents for metal-catalyzed cross-coupling reactions under protic conditions. Organogold(I) phosphanes react with organic electrophiles in aqueous media under palladium catalysis conditions. The reactions take place at room temperature or 80 °C in water with THF as co-solvent. The coupling is versatile and chemoselective and allows the presence of free amino and hydroxy groups in the electrophile. Copyright

Facile synthesis of mono-, bis- and tris-aryl-substituted aniline derivatives in aqueous DMF

A facile, efficient and general protocol for synthesizing a series of mono-, bis- and tris-arylsubstituted aniline derivatives is described via the Pd(OAc)2-catalyzed aerobic and ligand-free Suzuki reaction of mono-, di- and tribromoanilines with aryl boronic acids in aqueous N,Ndimethylformamide (DMF). This is the first example to prepare 2,6-bisaryl-4-nitroanilines and 2,6-bisarylanilines via a palladium-catalyzed ligand-free Suzuki reaction.

The 1,3-diaminobenzene-derived aminophosphine palladium pincer complex {C6H3[NHP(piperidinyl)2]2Pd(Cl)} - A highly active Suzuki-Miyaura catalyst with excellent functional group tolerance

The rapidly prepared 1,3-diaminobenzenederived aminophosphine pincer complex {C6H3 [NHP(piperidinyl)2] 2Pd(Cl)} (1) is an effective Suzuki catalyst with excellent functional group tolerance. Side-product formations, such as homocoupling, debromation or protodeboration have only rarely been detected and if so, were in all cases below the 5% level. The presented reaction protocol is universally applicable. Experimental observations indicate that palladium nanoparticles are the catalytically active form of 1.

Fingerprints of singlet and triplet phenyl cations

The photolyses of seven phenyl cation precursors in acetonitrile in the presence of anisole resulted in four distinct product patterns. These patterns are due to the chemoselective and regioselective chemistry of various phenyl cation isomers. This spin-selective chemistry provides a tool with which to fingerprint the singlet/triplet nature of any phenyl cation. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Discovery and SAR study of novel dihydroquinoline containing glucocorticoid receptor ligands

We report the discovery of a novel class of glucocorticoid receptor (GR) ligands based on 1,2-dihydroquinoline molecular scaffold. The compounds exhibit good GR binding affinity and selectivity profile against other nuclear hormone receptors.

NOVEL HETEROCYCLIC AMIDE DERIVATIVES HAVING DIHYDROOROTATE DEHYDROGENASE INHIBITING ACTIVITY

Novel heterocyclic amide derivatives having pharmacological effects, that is, compounds represented by the general formula (1) or salts thereof: (1) wherein X1-X2 is S-CH2 or the like; R1 is alkyl or the like; p is 0 to 7; R2 is hydrogen, alkyl, or the like; R3 is hydrogen, alkyl, or the like; Y1-Y2 is CH=CH or the like; R4 is halogeno, alkyl, or the like; q is 0 to 4; and R5 is halogeno, hydrogen, alkyl, or the like.

GLUCOCORTICOID MIMETICS, METHODS OF MAKING THEM, PHARMACEUTICAL COMPOSITIONS, AND USES THEREOF

Compounds of Formula (I) wherein R1, R2, R3, R4, R5, R6, X, Y, and n are as defined herein, or a tautomer, prodrug, solvate, or salt thereof; pharmaceutical compositions containing such compounds, and methods of modulating the glucocorticoid receptor function and methods of treating disease-states or conditions mediated by the glucocorticoid receptor function or characterized by inflammatory, allergic, or proliferative processes in a patient using these compounds.