81764-16-1

Basic information

• Product Name: 4-Chloro-8-aminoquinoline
• Synonyms: 4-Chloro-8-aminoquinoline;4-Chloro-8-quinolylaMine;4-Chloroquinolin-8-aMine
• CAS NO: 81764-16-1
• Molecular Formula: C₉H₇ClN₂
• Molecular Weight: 179
• Mol File: 81764-16-1.mol

Chemical Properties

• Melting Point: 99-100 °C
• Boiling Point: 333.7±27.0 °C(Predicted)
• Appearance: /
• Density: 1.363±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 2.65±0.13(Predicted)
• CAS DataBase Reference: 4-Chloro-8-aminoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-8-aminoquinoline(81764-16-1)
• EPA Substance Registry System: 4-Chloro-8-aminoquinoline(81764-16-1)

Safety Data

• Hazardous Substances Data: 81764-16-1(Hazardous Substances Data)

Usage

Chemical Properties

Yellow solid

Upstream product

• 611-35-8 4-chloroquinoline 
• 23833-95-6 8-nitro-4(1H)-quinolinone 
• 25063-47-2 2,2-dimethyl-5-(((2-nitrophenyl)amino)methylene)-1,3-dioxane-4,6-dione 
• 88-74-4 2-nitro-aniline 
• 611-36-9 quinolin-4-ol 
• 22200-50-6 4-chloro-7-iodoquinoline 
• 22297-71-8 7-iodo-quinolin-4-ol 
• 75698-26-9 4-chloro-7-iodo-8-nitroquinoline 
• 23833-99-0 4-chloro-8-nitroquinoline 

Downstream Products

• 49713-55-5 4-chloro-8-iodoquinoline 
• 53867-96-2 4-ethoxyquinolin-8-amine 
• 1313019-87-2 N-(3-(8-aminoquinolin-4-yloxy)phenyl)-3,5-bis(trifluoromethyl)benzamide 
• 1313019-84-9 N-(4-(8-aminoquinolin-4-yloxy)-2-methylphenyl)-3,5-bis(trifluoromethyl)benzamide 
• 190140-43-3 4-chloro-8-(2-nitrobenzoylamino)quinoline 

Relevant articles and documents

Direct amination of nitroquinoline derivatives via nucleophilic displacement of aromatic hydrogen

The vicarious nucleophilic substitution of hydrogen (VNS) reaction in electron-deficient nitroquinolines was studied. Properties of all new products have been characterized by several techniques: MS, HRMS, FTIR, GC-MS, electronic absorption spectroscopy, and multinuclear NMR. The structures of 4-chloro-8-nitroquinoline, 8-(tert-butyl)-2-methyl-5-nitroquinoline, 9-(8nitroquinolin-7-yl)-9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one were determined by single-crystal X-ray diffraction measurements. The 9-(8-nitroquinolin-7-yl)9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one illustrate the nitro/nitroso conversion within VNS reaction. Additionally, 9-(8-isopropyl-2-((8-isopropyl-2-methyl5-nitroquinolin-6-yl)methyl)-5-nitrosoquinolin-6-yl)-9H-carbazole is presented as a double VNS product. It is postulated that the potassium counterion interacts with the oxygen on the nitro group, which could influence nucleophile attack in that way.

Effects of the Distance between Radical Sites on the Reactivities of Aromatic Biradicals

Coupling of the radical sites in isomeric benzynes is known to hinder their radical reactivity. In order to determine how far apart the radical sites must be for them not to interact, the gas-phase reactivity of several isomeric protonated (iso)quinoline-and acridine-based biradicals was examined. All the (iso)quinolinium-based biradicals were found to react slower than the related monoradicals with similar vertical electron affinities (i.e., similar polar effects). In sharp contrast, the acridinium-based biradicals, most with the radical sites farther apart than in the (iso)quinolinium-based systems, showed greater reactivities than the relevant monoradicals with similar vertical electron affinities. The greater distances between the two radical sites in these biradicals lead to very little or no spin-spin coupling, and no suppression of radical reactivity was observed. Therefore, the radical sites can still interact if they are located on adjacent benzene rings and only after being separated further than that does no coupling occur. The most reactive radical site of each biradical was experimentally determined to be the one predicted to be more reactive based on the monoradical reactivity data. Therefore, the calculated vertical electron affinities of relevant monoradicals can be used to predict which radical site is most reactive in the biradicals.

BICYCLIC COMPOUNDS AS mPGES-1 INHIBITORS

The present disclosure is directed to compounds of formula (I), and pharmaceutically acceptable salts thereof, as mPGES-1 inhibitors. These compounds are inhibitors of the microsomal prostaglandin E synthase-1 (mPGES-1) enzyme and are therefore useful in the treatment of pain and/or inflammation from a variety of diseases or conditions, such as asthma, osteoarthritis, rheumatoid arthritis, acute or chronic pain and neurodegenerative diseases.

Substituent-dependent fluorescent sensors for zinc ions based on carboxamidoquinoline

A series of carboxamidoquinoline-based fluorescent sensors (the AQZ family) were synthesized and characterized. The AQZ family members were highly soluble in water and showed good selectivity for Zn2+via enhanced fluorescence in aqueous buffer solution. Fluorescence signals could be tuned from dual-wavelength ratiometric changes to changes in the intensity of a single wavelength upon binding Zn2+ through the introduction of different substituents onto the quinoline ring. Concentrations of free Zn2+ of 10-5-10-6 M could be detected using the sensors. Changes of substituents and their positions on the quinoline ring influenced the sensitivity for Zn2+, but had little effect on Zn2+ affinities.

SYNTHESIS OF DERIVATIVES OF 7-IODO-4-AMINOQUINOLINES

7-Iodo- and 7,8-diiodo-4-(3-dimethylaminopropylamino)quinolines and 7-iodo-4-(3-dipropylaminopropylamino)- and 7-iodo-4-(3-diallylaminopropylamino)quinoline were obtained by the reaction of 7-iodo- and 7,8-diiodo-4-chloroquinolines with the the corresponding diamines.The catalytic hydrogenation of 7-iodo-4-(3-diallylaminopropylamino)quinoline at normal pressure leads to 7-iodo-4-(3-dipropylaminopropylamino)quinoline.