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

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

Downstream Products

• 385408-19-5 N-benzylidene-N'-(2-naphthyl)hydrazine 
• 859960-95-5 2-[2]naphthyl-4-phenyl thiosemicarbazide 
• 40880-56-6 N′-(naphthalen-2-yl)acetohydrazide 
• 41532-84-7 2,3,3-trimethylbenzo[e]indole 
• 194-59-2 7H-dibenzo[c,g]carbazole 
• 4488-22-6 1,1'-binaphthalene-2,2'-diamine 
• 91-20-3 naphthalene 
• 57582-31-7 2-methyl-1H-benz[e]indole 
• 117044-44-7 8-methyl-7H-benzo[c]carbazole 
• 1416983-49-7 C₁₇H₁₆N₂O₂S 
• 76877-00-4 1-(2-naphthylamino)-5-carboxy-4,6-dimethyl-2(1H)-pyridone 
• 52831-67-1 Dihydro-6,13-fluor-4(I)benzothiopyrano<4,3-b>benzoindol 

Relevant articles and documents

Visible-light-mediated phosphonylation reaction: formation of phosphonates from alkyl/arylhydrazines and trialkylphosphites using zinc phthalocyanine

In this work, we developed a ligand- and base-free visible-light-mediated protocol for the photoredox syntheses of arylphosphonates and, for the first time, alkyl phosphonates. Zinc phthalocyanine-photocatalyzed Csp2-P and Csp3-P bond formations were efficiently achieved by reacting aryl/alkylhydrazines with trialkylphosphites in the presence of air serving as an abundant oxidant. The reaction conditions tolerated a wide variety of functional groups.

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).