2243-57-4

Basic information

• Product Name: 2-Naphthylhydrazine
• Synonyms: BETA-NAPHTHYL HYDRAZINE;AKOS AUF0417;2-NAPHTHALENYL HYDRAZINE HYDROCHLORIDE;2-NAPHTHYLHYDRAINE HYDROCHLORIDE;2-NAPHTHYL HYDRAZINE;2-HYDRAZINONAPHTHALENE;2-HYDRAZINONAPHTHALENE HYDROCHLORIDE;N'-NAPHTHALEN-2-YL-HYDRAZINE HCL
• CAS NO: 2243-57-4
• Molecular Formula: C₁₀H₁₀N₂
• Molecular Weight: 158.2
• Product Categories: Naphthalene derivatives
• Mol File: 2243-57-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 362.936 °C at 760 mmHg
• Flash Point: 203.929 °C
• Appearance: /
• Density: 1.215 g/cm³
• Vapor Pressure: 1.87E-05mmHg at 25°C
• Refractive Index: 1.742
• PKA: 5.66±0.70(Predicted)
• CAS DataBase Reference: 2-Naphthylhydrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Naphthylhydrazine(2243-57-4)
• EPA Substance Registry System: 2-Naphthylhydrazine(2243-57-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 2243-57-4(Hazardous Substances Data)

Usage

General Description

2-Naphthylhydrazine is an organic chemical compound with the formula C10H9N2. It is a derivative of hydrazine and consists of a naphthalene ring with a hydrazine functional group attached. 2-Naphthylhydrazine is commonly used in the synthesis of various pharmaceuticals, dyes, and rubber chemicals. 2-Naphthylhydrazine has also been studied for its potential as a mutagen and carcinogen, and is considered to be toxic. It is important to handle this compound with caution and follow proper safety protocols when working with it.

InChI:InChI=1/C10H10N2/c11-12-10-6-5-8-3-1-2-4-9(8)7-10/h1-7,12H,11H2

Upstream product

• 91-59-8 naphthalen-2-ylamine 
• 135-19-3 β-naphthol 
• 7803-57-8 hydrazine hydrate 
• 20893-80-5 naphthalene-2-diazonium chloride 
• 7385-85-5 naphthalen-2-yl tosylate 
• 580-13-2 2-bromonaphthalene 
• 91-58-7 2-chloronaphthalene 

Downstream Products

• 21410-17-3 2-(2,5-dimethyl-[3]thienyl)-1-phenyl-3H-benz[e]indole 
• 21064-52-8 7,8,9,11-tetrahydrobenzo[c]carbazole 
• 40880-56-6 N′-(naphthalen-2-yl)acetohydrazide 
• 385408-19-5 N-benzylidene-N'-(2-naphthyl)hydrazine 
• 93323-38-7 N’-(naphthalen-2-yl)benzohydrazide 
• 859960-95-5 2-[2]naphthyl-4-phenyl thiosemicarbazide 
• 54682-89-2 N-(2,4-dinitro-phenyl)-N'-[2]naphthyl-hydrazine 
• 41532-84-7 2,3,3-trimethylbenzo[e]indole 
• 194-59-2 7H-dibenzo[c,g]carbazole 

Relevant articles and documents

Cross-Coupling between Hydrazine and Aryl Halides with Hydroxide Base at Low Loadings of Palladium by Rate-Determining Deprotonation of Bound Hydrazine

Reported here is the Pd-catalyzed C–N coupling of hydrazine with (hetero)aryl chlorides and bromides to form aryl hydrazines with catalyst loadings as low as 100 ppm of Pd and KOH as base. Mechanistic studies revealed two catalyst resting states: an arylpalladium(II) hydroxide and arylpalladium(II) chloride. These compounds are present in two interconnected catalytic cycles and react with hydrazine and base or hydrazine alone to give the product. The selectivity of the hydroxide complex with hydrazine to form aryl over diaryl hydrazine was lower than that of the chloride complex, as well as the catalytic reaction. In contrast, the selectivity of the chloride complex closely matched that of the catalytic reaction, indicating that the aryl hydrazine is derived from this complex. Kinetic studies showed that the coupling process occurs by rate-limiting deprotonation of a hydrazine-bound arylpalladium(II) chloride complex to give an arylpalladium(II) hydrazido complex.

Diversification of edaravone via palladium-catalyzed hydrazine cross-coupling: Applications against protein misfolding and oligomerization of beta-amyloid

N-Aryl derivatives of edaravone were identified as potentially effective small molecule inhibitors of tau and beta-amyloid aggregation in the context of developing disease-modifying therapeutics for Alzheimer's disease (AD). Palladium-catalyzed hydrazine monoarylation protocols were then employed as an expedient means of preparing a focused library of 21 edaravone derivatives featuring varied N-aryl substitution, thereby enabling structure-activity relationship (SAR) studies. On the basis of data obtained from two functional biochemical assays examining the effect of edaravone derivatives on both fibril and oligomer formation, it was determined that derivatives featuring an N-biaryl motif were four-fold more potent than edaravone.

Palladium-catalyzed cross-coupling of aryl chlorides and tosylates with hydrazine

Hydrazine is not a problem anymore: The title transformation is the first reaction to yield aryl hydrazines through the cross-coupling of aryl chlorides and tosylates with hydrazine. An appropriately designed palladium catalyst allows this reaction to proceed rapidly under mild conditions, and with excellent chemoselectivity (see scheme; Ad=adamantyl, Ts=4-toluenesulfonyl).