177202-83-4

Basic information

• Product Name: 2-PYRIDIN-3-YLANILINE
• Synonyms: 2-PYRIDIN-3-YLANILINE;2-(Pyridin-3-yl)aniline 95%;2-pyridin-3-ylphenylaMine;3-(2-Aminophenyl)pyridine;2-(Pyridin-3-yl)aniline95%;2-PyridiN-3-Ylanili
• CAS NO: 177202-83-4
• Molecular Formula: C₁₁H₁₀N₂
• Molecular Weight: 170.21
• Mol File: 177202-83-4.mol

Chemical Properties

• Melting Point: 214-216 °C (decomp)(Solv: water (7732-18-5); ethanol (64-17-5))
• Boiling Point: 329.8 °C at 760 mmHg
• Flash Point: 179.5 °C
• Appearance: /
• Density: 1.133 g/cm³
• Vapor Pressure: 0.000174mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.55±0.12(Predicted)
• CAS DataBase Reference: 2-PYRIDIN-3-YLANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PYRIDIN-3-YLANILINE(177202-83-4)
• EPA Substance Registry System: 2-PYRIDIN-3-YLANILINE(177202-83-4)

Safety Data

• Hazardous Substances Data: 177202-83-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Pyridin-3-ylaniline is used as a building block for various organic synthesis reactions, particularly in the development of new drugs. Its antioxidant and anti-inflammatory properties make it a valuable component in the formulation of medications aimed at treating a variety of diseases.
Used in Coordination Chemistry:
2-Pyridin-3-ylaniline is utilized as a ligand in coordination chemistry, where it can form complexes with metal ions. This application is significant for the study of metal-organic frameworks and the development of new materials with specific properties.
Used in Synthesis of Heterocyclic Compounds:
In the field of organic chemistry, 2-Pyridin-3-ylaniline is employed in the synthesis of heterocyclic compounds, which are important in the creation of pharmaceuticals, agrochemicals, and other specialty chemicals due to their diverse and complex molecular structures.

InChI:InChI=1/C11H10N2/c12-11-6-2-1-5-10(11)9-4-3-7-13-8-9/h1-8H,12H2

Upstream product

• 4253-80-9 3-(2-nitro-phenyl)-pyridine 
• 626-55-1 3-Bromopyridine 
• 191171-55-8 2-anilineboronic acid pinacol ester 
• 110-86-1 pyridine 
• 615-43-0 2-iodophenylamine 
• 615-36-1 2-bromoaniline 
• 160688-99-3 [tris(3-pyridyl)boroxin] 
• 185408-20-2 o-(tributylstannyl)aniline 
• 3422-01-3 tert-butyl phenylcarbamate 
• 148493-54-3 tributyl (o-tert-butyloxycarbonylaminophenyl) stannane 
• 577-19-5 2-nitrophenyl bromide 
• 1692-25-7 3-pyridylboronic acid 
• 59020-10-9 3-(tributylstannyl)pyridine 
• 220565-63-9 pyridin-3-ylzinc(II) bromide 

Downstream Products

• 855196-53-1 2-(pyridin-3-yl)benzonitrile 
• 856849-78-0 3-(2-azidophenyl)pyridine 
• 21777-15-1 (E)-3-(1H-indol-3-yl)acrylaldehyde 
• 695185-54-7 3-methyl-8-pyridin-3-yl-quinoline 
• 695185-50-3 2-piperidin-3-yl-phenylamine 
• 52817-50-2 benzo[f][1,7]naphthyridin-5(6H)-one 
• 1008-88-4 3-phenylpyridine 
• 23827-07-8 5-phenylbenzo[h]isoquinoline 
• 23827-05-6 5-phenylbenzo[f]quinoline 

Relevant articles and documents

Synthesis and deprotonation of 2-(pyridyl)phenols and 2-(pyridyl)anilines

2-(2- and 3-Pyridyl)anilines (1, 2), 2,2-dimethyl-N-[2-(2- and 3-pyridyl)phenyl]propanamides (3, 4), and 2-, 3- and 4-(2-methoxyphenyl)pyridines (7-9) are readily synthesized using cross-coupling reactions. Whereas the amines 1, 2 undergo side reactions, the corresponding amides 3, 4 are deprotonated with lithium 2,2,6,6-tetramethylpiperidide (LTMP): the compound 3 at C6′ under in situ quenching, and the compound 4 at C4′. When the ether 7 is subjected to the same reagent, lithiation occurs at C6′.

Pd-Catalyzed Remote Meta-C-H Functionalization of Phenylacetic Acids Using a Pyridine Template

An effective pyridine based U-shaped template has been developed to enable a diverse range of meta-C-H functionalizations of phenylacetic acid scaffolds. This new template has extended the reaction scope to cross-coupling with ArBF3K as well as iodination using 1,3-diiodo-5,5-dimethylhydantoin as the iodination reagent.

Rhodium(I)-Catalyzed Aryl C-H Carboxylation of 2-Arylanilines with CO2

An unprecedented Rh(I)-catalyzed, amino-group-assisted C-H carboxylation of 2-arylanilines with CO2 under redox-neutral conditions has been developed. This reaction was promoted by a phosphine ligand with t-BuOK as the base and did not require the use of additional strong organometallic reagent. It enabled an efficient direct conversion of a broad range of 2-(hetero)arylanilines including electron-deficient heteroarenes to various phenanthridinones. Possible intermediates of the reaction were also evaluated in the preliminary mechanistic studies.

Visible-light-induced regioselective synthesis of polyheteroaromatic compounds

A method for visible-light-induced synthesis of polyheteroaromatics from 2-heteroaryl-substituted anilines and heteroarylalkynes was developed. The process, which uses fac-Ir(ppy)3 as the photocatalyst and tBuONO as the diazotization reagent, is highly regioselective.

Efficient 11C-carbonylation of isolated aryl palladium complexes for PET: Application to challenging radiopharmaceutical synthesis

We describe the successful implementation of palladium-aryl oxidative addition complexes as stoichiometric reagents in carbonylation reactions with 11CO to produce structurally challenging, pharmaceutically relevant compounds. This method enables the first 11C-carbonyl labeling of an approved PET tracer, [11C]raclopride, for the dopamine D2/D3 receptor by carbonylation with excellent radiochemical purity and yield. Two other molecules, [11C]olaparib and [11C]JNJ 31020028, were efficiently labeled in this manner. The technique distinguishes itself from existing methods by the markedly improved purity profiles of the tracer molecules produced and provides access to complex structures in synthetically useful yields, hereby offering a viable alternative to other 11C-labeling strategies.

N-Sulfonyl-aminobiaryls as Antitubulin Agents and Inhibitors of Signal Transducers and Activators of Transcription 3 (STAT3) Signaling

A series of N-sulfonyl-aminobiaryl derivatives have been examined as novel antitubulin agents. Compound 21 [N-(4′-cyano-3′-fluoro-biphenyl-2-yl)-4-methoxy-benzenesulfonamide] exhibits remarkable antiproliferative activity against four cancer cell lines (pancreatic AsPC-1, lung A549, liver Hep3B, and prostate PC-3) with a mean GI50 value of 57.5 nM. Additional assays reveal that 21 inhibits not only tubulin polymerization but also the phosphorylation of STAT3 inhibition with an IC50 value of 0.2 μM. Four additional compounds (8, 10, 19, and 35) are also able to inhibit this phosphorylation. This study describes novel N-sulfonyl-aminobiaryl (biaryl-benzenesulfonamides) as potent anticancer agents targeting both STAT3 and tubulin. (Chemical Equation Presented).

Synthesis and evaluation of imidazole-4,5-and pyrazine-2,3-dicarboxamides targeting dengue and yellow fever virus

The results of a high-throughput screening assay using the dengue virus-2 replicon showed that the imidazole 4,5-dicarboxamide (I45DC) derivative (15a) has a high dengue virus inhibitory activity. Based on 15a as a lead compound, a novel class of both disubstituted I45DCs and the resembling pyrazine 2,3-dicarboxamides (P23DCs) were synthesized. Here, we report on their in vitro inhibitory activity against dengue virus (DENV) and yellow fever virus (YFV). Some of these first generation compounds have shown activity against both viruses in the micromolar range. Within this series, compound 15b was observed to display the highest antiviral potency against YFV with an EC50 Combining double low line 1.85 μM. In addition, compounds 20a and 20b both potently inhibited replication of DENV (EC50 Combining double low line 0.93 μM) in Vero cells.

Facile synthesis of 3-arylpyridine derivatives by palladacycle-catalyzed Stille cross-coupling reaction

The Stille cross-coupling reaction of a variety of aryl halides (X=Cl, Br, I) with 3-alkylstannylpyridines highly catalyzed by cyclopalladated ferrocenylimine has been developed. This reaction allows formation of arylpyridine derivatives in moderate to excellent yields. Functional groups on aryl halides, such as amino, hydroxyl, keto, and aldehyde are tolerated and the reactions with arylbenzoxale substrates also proceed well.

O-(Trialkylstannyl)anilines and their utility in Migita-Kosugi-Stille cross-coupling: Direct introduction of the 2-aminophenyl substituent

We have developed shelf- and air-stable ortho-stannylated aniline reagents that can directly be coupled with alkenyl and aryl halides via Migita-Kosugi-Stille cross-coupling. We report (i) the efficient preparation of o-(tributylstannyl)aniline (2a) and o-(trimethylstannyl)aniline (2b), (ii) the comparison of the reactivities of 2a and 2b with those of related organostannanes in cross-coupling reaction with an alkenyl halide, and (iii) the cross-coupling of 2a and 2b with a series of arylhalides and triflate.

RhII2-catalyzed synthesis of α-, β-, or δ-carbolines from aryl azides

Approaching all isomers: A range of α-, β- and δ-carbolinium ions are readily available from ortho-substituted aryl azides using a rhodium(II) carboxylate catalyst (see scheme). The carbolinium ions are readily reduced to afford tryptolines or deprotonated to access pyridoindoles. This [RhII2]-catalyzed C-H bond amination was used in the synthesis of (±)-horsfiline and neocryptolepine. esp=α,α,α',α'- tetramethyl-1,3-benzenedipropionate. Copyright