611-34-7

Basic information

• Product Name: 5-Aminoquinoline
• Synonyms: QUINOLIN-5-AMINE;QUINOLIN-5-YLAMINE;TIMTEC-BB SBB010065;5-amino-quinolin;5-Quinolylamine;Quinoline, 5-amino-;IFLAB-BB F2124-0039;ASISCHEM Z74663
• CAS NO: 611-34-7
• Molecular Formula: C₉H₈N₂
• Molecular Weight: 144.17
• EINECS: 210-266-1
• Product Categories: Amines and Anilines;Heterocycles;Quinolines, Quinazolines and derivatives;Quinoline&Isoquinoline;Quinolines;Quinoline Derivertives;Aromatics Compounds;Aminoquinolines;Aromatics;Amines;Pharmaceutical intermdiate
• Mol File: 611-34-7.mol
• Article Data: 53

Chemical Properties

• Melting Point: 106-109 °C(lit.)
• Boiling Point: 310 °C(lit.)
• Flash Point: 310°C
• Appearance: White to slightly yellow/Crystalline Powder or Granules
• Density: 1.1148 (estimate)
• Vapor Pressure: 0.000617mmHg at 25°C
• Refractive Index: 1.7080 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO, Methanol
• PKA: pK1: 5.46(+1) (20°C,μ=0.01)
• Sensitive: Air Sensitive
• BRN: 114479
• CAS DataBase Reference: 5-Aminoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Aminoquinoline(611-34-7)
• EPA Substance Registry System: 5-Aminoquinoline(611-34-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: VA9625000
• F: 2-10
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 611-34-7(Hazardous Substances Data)

Usage

Chemical Properties

Reddish-Brown Solid

Uses

Intermediate in the preparation of P2X7 antagonists

Application

5-Aminoquinoline can be used as organic synthesis and as intermediates of medicine and pesticide.

Preparation

Under the catalysis of Pd/C, 95% ethanol was used as solvent to reduce 5-nitroquinoline with hydrazine hydrate to synthesize 5-aminoquinoline with a yield of 91.11%.

InChI:InChI=1/C9H8N2/c10-8-4-1-5-9-7(8)3-2-6-11-9/h1-6H,10H2

Upstream product

• 873969-81-4 3-chloro-[5]quinolylamine 
• 607-34-1 5-nitroquinoline 
• 860195-55-7 3-bromo-5-nitro-quinoline-1-oxide 
• 578-67-6 quinolin-5-ol 
• 7462-74-0 2-bromo-2-methylpropanamide 
• 91-22-5 quinoline 
• 116529-79-4 3-chloro-5-nitro-quinoline 
• 872-50-4 1-methyl-pyrrolidin-2-one 
• 1202748-38-6 methyl 4-[(5-quinolinylimino)methyl]benzoate 
• 4964-71-0 5-bromoquinoline 
• 111-26-2 hexan-1-amine 
• 20377-01-9 5-quinolyl azide 
• 7613-19-6 5-nitro-quinoline-1-oxide 
• 613-51-4 7-nitroquinoline 

Downstream Products

• 72041-92-0 N-tert-Butyl-N'-quinolin-5-yl-N''-thiazol-2-yl-guanidine 
• 91221-14-6 3-(Quinolin-5-ylaminomethyl)-5-p-tolyl-3H-[1,3,4]thiadiazole-2-thione 
• 91221-15-7 5-(4-Chloro-phenyl)-3-(quinolin-5-ylaminomethyl)-3H-[1,3,4]thiadiazole-2-thione 
• 10470-83-4 5,8-quinolinedione 
• 20377-01-9 5-quinolyl azide 
• 4964-71-0 5-bromoquinoline 
• 394-69-4 5-fluoroquinoline 
• 369652-60-8 2-(5-quinolineamino)-3-nitrobenzoic acid 
• 111880-40-1 N-(5-quinolyl)anthranilic acid 
• 635-27-8 5-chloroquinoline 
• 714969-91-2 [2-phenyl-1-(quinolin-5-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 
• 736930-12-4 N-(2-bromo-4,5-dimethoxybenzyl)-5-quinolinamine 
• 861208-64-2 1-benzoyl-3-quinolin-5-yl-thiourea 
• 1001183-84-1 5-isothiocyanatoquinoline 

Relevant articles and documents

Method for preparing amine through catalytic reduction of nitro compound by cyclic (alkyl) (amino) carbene chromium complex

The cyclic (alkyl) (amino) carbene chromium complex is prepared from corresponding ligand salt, alkali and CrCl3 and used for catalyzing pinacol borane to reduce nitro compounds in an ether solvent under mild conditions to generate corresponding amine. The method for preparing amine has the advantages of cheap and accessible raw materials, mild reaction conditions, wide substrate application range, high selectivity and the like, and is simple to operate.

Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications

Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 × 106). Mechanistic studies, based on theoretical calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several commercially available pharmaceuticals by means of this strategy highlights its potential application in medicinal chemistry.

Method for reducing aromatic nitro into arylamine

The invention relates to a method for reducing aromatic nitro to arylamine. The method comprises the following steps: (1) taking an aromatic nitro compound as a raw material, water as a hydrogen source, a palladium compound, cheap and easy to obtain, as a catalyst and tetrahydroxydiboron as an additive to reduce nitro to obtain a product; (2) taking the aromatic nitro compound as the raw material, a copper salt, cheap and easy to obtain, as the catalyst, the tetrahydroxydiboron as the additive to reduce the nitro to obtain a product; and (3) taking the aromatic nitro compound as the raw material, water as the hydrogen source, and the tetrahydroxydiboron as the additive, without needing a metal catalyst, to reduce the nitro to obtain a product. A preparation method for the arylamine, which is provided by the invention, is mild in reaction condition, low in costs, environment-friendly, high in yield, and suitable for industrial production.