4-hydrazinylpyridine hydrochloride

Base Information

• Chemical Name: 4-hydrazinylpyridine hydrochloride
• CAS No.: 27256-91-3
• Molecular Formula: C5H7N3
• Molecular Weight: 109.131
• Hs Code.: 2933399990
• Mol file: 27256-91-3.mol

Synonyms:Pyridine,4-hydrazino- (6CI,7CI,8CI,9CI);4-Hydrazinopyridine;4-Pyridinylhydrazine;4-Pyridylhydrazine;

Chemical Property of 4-hydrazinylpyridine hydrochloride

Chemical Property:

• Vapor Pressure: 0.00265mmHg at 25°C
• Melting Point: 30 °C
• Refractive Index: 1.657
• Boiling Point: 286.4 °C at 760 mmHg
• PKA: 8.24±0.26(Predicted)
• Flash Point: 127 °C
• PSA: 50.94000
• Density: 1.222 g/cm³
• LogP: 1.14050

Purity/Quality:

99%, ^*data from raw suppliers

4-Hydrazinylpyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 4-Hydrazinylpyridine hydrochloride (also known as 4-hydrazinopyridine or 4-pyridylhydrazine) is a key intermediate formed during the reductive condensation of trichloromethylarenes with hydrazines in pyridine. It arises from the oxidation of pyridine to N-(4-pyridyl)pyridinium salts, which subsequently react with hydrazine. 4-hydrazinylpyridine hydrochloride further participates in reactions to yield derivatives such as 4-pyridylhydrazones, highlighting its role in generating unusual products. The study underscores its unexpected formation and significance in the reaction mechanism, demonstrating pyridine's active involvement beyond its traditional solvent or base functions.

Technology Process of 4-hydrazinylpyridine hydrochloride

There total 10 articles about 4-hydrazinylpyridine hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

4-hydrazinopyridine hydrochloride (20815-52-5) → 4-pyridylhydrazine (27256-91-3)

Guidance literature:

With ion-exchange resin Ambersep 900-OH (Fluka); In methanol;

Reference yield: 89.0%

4-bromopyridine hydrobromide salt (74129-11-6) → 4-pyridylhydrazine (27256-91-3)

Guidance literature:

With hydrazine hydrate; for 2h; Reflux;

DOI:10.1002/ardp.201800247

Reference yield: 88.0%

4-chlorpyridine hydrochloride (7379-35-3) → 4-pyridylhydrazine (27256-91-3)

Guidance literature:

With hydrazine hydrate;

upstream raw materials:

4-Chloropyridine

4-(nitroamino)pyridine

hydrogenchloride

4-chlorpyridine hydrochloride

Downstream raw materials:

N-(3-phenyl-propylidene)-N'-pyridin-4-yl-hydrazine

N-[3-(4-methoxy-phenyl)-propylidene]-N'-pyridin-4-yl-hydrazine

N-[3-(3-methoxy-phenyl)-propylidene]-N'-pyridin-4-yl-hydrazine

N-{3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-propylidene}-N'-pyridin-4-yl-hydrazine

Refernces

Initial steps in the reductive condensation of trichloromethylarenes with hydroxylamine and hydrazines in pyridine

10.1007/BF00699000

The research investigates the initial steps of the reductive condensation of trichloromethylarenes with hydroxylamine or hydrazines in pyridine. The purpose is to understand the role of pyridine in these reactions and the initial steps of the reductive condensation process. The key chemicals used include trichloromethylarenes, hydroxylamine hydrochloride, hydrazine salts, and pyridine. The study found that pyridine may act as the actual reducing agent, undergoing oxidation to form N-(4-pyridyl)pyridinium salts, which then react with hydrazine to produce 4-pyridylhydrazine. This compound further reacts to form unusual products like 4-pyridylhydrazones of substituted benzaldehydes. The research concludes that pyridine plays a more complex role than previously thought, contributing significantly to the high yields of certain products even at equimolar ratios of reactants. In the research, hydroxylamine hydrochloride plays a crucial role as a reagent in the reductive condensation process. 4-pyridylhydrazine is identified as an unexpected and significant product formed during the reductive condensation process involving pyridine.

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