25551-59-1

Basic information

• Product Name: 4-(2-Nitroanilino)-pyridine
• Synonyms: 4-(2-Nitroanilino)-pyridine;(2-Nitrophenyl)pyridin-4-yl-amine;4-[(2-Nitrophenyl)amino]pyridine;N-(2-Nitrophenyl)pyridin-4-amine, 4-(2-Nitroanilino)pyridine;(2-Nitrophenyl)pyridine-4-yl-amine;Zinc03953266;4-PyridinaMine,N-(2-nitrophenyl)-;N-(2-Nitrophenyl)pyridin-4-aMine
• CAS NO: 25551-59-1
• Molecular Formula: C₁₁H₉N₃O₂
• Molecular Weight: 215.20806
• Mol File: 25551-59-1.mol

Chemical Properties

• Melting Point: 81-82 °C
• Boiling Point: 379.9 °C at 760 mmHg
• Flash Point: 183.5 °C
• Appearance: /
• Density: 1.34 g/cm³
• Vapor Pressure: 5.68E-06mmHg at 25°C
• Refractive Index: 1.674
• Storage Temp.: 2-8°C
• PKA: 6.95±0.26(Predicted)
• CAS DataBase Reference: 4-(2-Nitroanilino)-pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-Nitroanilino)-pyridine(25551-59-1)
• EPA Substance Registry System: 4-(2-Nitroanilino)-pyridine(25551-59-1)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 25551-59-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
4-(2-Nitroanilino)-pyridine is used as a chemical intermediate for the synthesis of 4-(2-Aminoanilino)pyridine (A583160) dihydrochloride, which is a compound with potential pharmaceutical applications. The conversion is achieved through hydrogenation in the presence of a Ni-Cr catalyst, which increases the yield of the desired product.
Used in the Production of Droperidol Impurity 4:
In the pharmaceutical industry, 4-(2-Nitroanilino)-pyridine is also utilized in the production of Droperidol Impurity 4. Droperidol is a medication used to treat anxiety, agitation, and hallucinations, and the synthesis of its impurities is essential for quality control and safety assessments in the manufacturing process.

InChI:InChI=1/C11H9N3O2/c15-14(16)11-4-2-1-3-10(11)13-9-5-7-12-8-6-9/h1-8H,(H,12,13)

Upstream product

• 14527-90-3 2-nitroaniline hydrochloride 
• 22752-98-3 N-Pyrid-4-yl-pyridiniumchlorid-hydrochlorid 

Downstream Products

• 65053-26-1 N-γ-pyridyl-o-phenylenediamine 

Relevant articles and documents

Synthetic Applications of N-N Linked Heterocycles. Part 15. A Facile Synthesis of 4-Pyridyl(aryl)amines via the Reaction between 4-Chloro-1-pyridiniopyridinium Salts and Aryl Amines

4-Chloro-1-pyridiniopyridinium salts (7) and (8) react with primary and secondary arylamines to give high yields of isolable 4-aryliminium salts (9) and (10).These are readily fragmented into 4-pyridyl(aryl)amines (11) and (12) in excellent yields on treatment with sodium cyanide or sodium salts of sulphonic acids.The method fails with the more basic aliphatic amines, since these apparently attack the 2-position of the chloropyridinium ring giving products resulting from ring-opening.Mechanisms of the reactions are discussed.