6460-91-9

Basic information

• Product Name: 1,1'-Biphenyl, 2-methoxy-4'-nitro-
• CAS NO: 6460-91-9
• Molecular Formula: C13H11NO3
• Molecular Weight: 229.235
• Mol File: 6460-91-9.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: 1,1'-Biphenyl, 2-methoxy-4'-nitro-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-Biphenyl, 2-methoxy-4'-nitro-(6460-91-9)
• EPA Substance Registry System: 1,1'-Biphenyl, 2-methoxy-4'-nitro-(6460-91-9)

Safety Data

• Hazardous Substances Data: 6460-91-9(Hazardous Substances Data)

Usage

Structure

A biphenyl derivative with a methoxy group and a nitro group

Appearance

Pale yellow solid

Melting point

121-122°C

Uses

a. Organic synthesis
b. Building block for various organic compounds
c. Reagent in chemical reactions
d. Precursor in the synthesis of pharmaceuticals, dyes, and fine chemicals

Potential applications

a. Medicine
b. Biochemistry

Biological activities

May have properties that contribute to its potential use in medicine and biochemistry
These properties and specific content are based on the information provided about 1,1'-Biphenyl, 2-methoxy-4'-nitro-.

Upstream product

• 5720-06-9 2-Methoxyphenylboronic acid 
• 586-78-7 para-nitrophenyl bromide 
• 636-98-6 p-nitrobenzene iodide 
• 100-66-3 methoxybenzene 
• 100-00-5 4-chlorobenzonitrile 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 100-01-6 4-nitro-aniline 
• 16186-97-3 α-(4-nitrophenylazo)triphenylmethane 

Downstream Products

• 263901-48-0 2'-Methoxy-biphenyl-4-ylamine 
• 666726-32-5 6-(2-methoxybiphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline 
• 666726-33-6 4-bromomethyl-6-(2-methoxybiphenyl)-2,2,-dimethyl-1,2-dihydroquinoline 
• 39117-68-5 2,4,6-trimethyl-4'-nitro-1,1'-biphenyl 

Relevant articles and documents

Competent synthesis of biaryl analogs via asymmetric Suzuki–Miyaura cross-coupling for the development of anti-inflammatory and analgesic agents

Based on the core structure of diflunisal drug, herein, we report a resembling series of biaryl analogs (3a–j) containing halogens, nitro, and methoxy substituents. They were designed and synthesized via a Suzuki–Miyaura cross-coupling reaction using Pd (OH)2 as a catalyst at a temperature of 65?°C with an intent to obtain improved and safer anti-inflammatory and analgesic agents. Suzuki–Miyaura transformation is the most significant among the cross-coupling reactions since its practical advantages include the commercially available low toxic reagents, mild reaction conditions, and functional group compatibility. On the other hand, a few conditions can be used to cross-couple aryl boronic acids or esters with aryl halides, especially 2-benzyl halides. Because of this, a novel Suzuki–Miyaura protocol is investigated that facilitates the selective conversion of halo aromatics, with an emphasis on the reaction to convert substituted bromobenzene to conjugated biphenyls. Finally, the obtained biaryl analogs (3a–j) were tested for in vitro and in vivo anti-inflammatory and analgesic applications. The results showed that compound 3b performed better than the standard drug with IC50 values comparable to that of the standard drug for COX-1 and COX-2 inhibition. Finally, molecular docking tests for the effective compound were carried out.

Sublimable bis(β-iminoenolate)palladium(II) complexes and their application as catalysts in Suzuki-Miyaura reactions

The Pd(II) complexes strongly chelated by two β-iminoenolate ligands were easily synthesized in only two steps, and purified based on their sublimable and highly stable property. The Pd(II) complexes anchored on a silica surface showed good catalytic activity in Suzuki-Miyaura reactions (up to 99% yield with 0.05 mol% catalyst). They tolerated a wide range of temperature (rt～110 °C) and various solvents, and could be reused multiple times after simple recovering process.

Suzuki-Miyaura cross-coupling reaction of aryl chlorides with aryl boronic acids catalyzed by a palladium dichloride adduct of N-diphenylphosphanyl-2-aminopyridine

One palladium dichloride adduct of a phosphine-pyridine ligand N-diphenylphosphanyl-2-aminopyridine (L1) [(L1)PdCl2] (1) has been prepared and structurally characterized. Compound 1 can be used as an effective catalyst for the Suzuki-Miyaura cross-coupling reactions of unreactive aryl chlorides with aryl boronic acids, and worked much better than its mono- or bidentate phosphine ligands. The reactions with a wide scope of substrates proceeded to give desired products in good to excellent yields.