35975-00-9

Basic information

• Product Name: 5-Amino-6-nitroquinoline
• Synonyms: 5-Quinolinamine, 6-nitro-;OTAVA-BB BB7110952630;TIMTEC-BB SBB000273;6-NITRO-5-QUINOLINAMINE;6-NITRO-5-QUINOLINEAMINE;6-NITROQUINOLIN-5-AMINE;AKOS BBS-00001337;AKOS AUF02029
• CAS NO: 35975-00-9
• Molecular Formula: C₉H₇N₃O₂
• Molecular Weight: 189.17
• EINECS: 252-822-6
• Product Categories: API intermediates;Building Blocks;Heterocyclic Building Blocks;Quinolines
• Mol File: 35975-00-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 272-273 °C (dec.)(lit.)
• Boiling Point: 324.42°C (rough estimate)
• Flash Point: 201.4°C
• Appearance: /
• Density: 1.3249 (rough estimate)
• Vapor Pressure: 6.5E-07mmHg at 25°C
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 3.81±0.15(Predicted)
• Stability: Hygroscopic
• BRN: 166360
• CAS DataBase Reference: 5-Amino-6-nitroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-6-nitroquinoline(35975-00-9)
• EPA Substance Registry System: 5-Amino-6-nitroquinoline(35975-00-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• PackingGroup: III
• Hazardous Substances Data: 35975-00-9(Hazardous Substances Data)

Usage

Chemical Properties

ochre-yellow fluffy powder

Uses

5-Amino-6-nitroquinoline was used in preparation of imidazoquinoline derivatives.

General Description

Electrochemical reduction of 5-amino-6-nitroquinoline has been studied at carbon paste electrode by differential pulse voltammetry, direct current voltammetry, adsorptive stripping voltammetry and HPLC with electrochemical detection.

InChI:InChI=1/C9H7N3O2/c10-9-6-2-1-5-11-7(6)3-4-8(9)12(13)14/h1-5H,10H2

Upstream product

• 613-50-3 6-nitroquinoline 
• 100-01-6 4-nitro-aniline 
• 74-89-5 methylamine 

Downstream Products

• 233-55-6 imidazo<4,5-f>quinoline 
• 93201-85-5 2-methyl-1(3)H-imidazo[4,5-f]quinoline 
• 42143-23-7 5,6-diaminoquinoline 
• 233-55-6 imidazo<4,5-f>quinoline 
• 79834-28-9 6,7-Dihydro-N⁶-methyl-7-phenyl-1,2,5-selenadiazolo<3,4-f>quinoline 
• 82050-10-0 2-amino-3-trideuteromethylimidazo[4,5-f]quinoline 
• 102408-25-3 2-amino-1-methylimidazo[4,5-f]-quinoline 
• 76180-96-6 2-Amino-3-methylimidazo[4,5-f]quinoline 

Relevant articles and documents

Vicarious nucleophilic amination of nitroquinolines by 1,1,1- trimethylhydrazinium iodide

(Chemical Equation Presented) The amination of 3-, 5-, 6-, 7- and 8-nitroquinoline via the vicarious nucleophilic substitution of hydrogen (VNS) with 1,1,1-trimethylhydrazinium iodide (TMHI) in the presence of t-BuOK in DMSO was studied. The amination occurs regioselectively giving ortho or ortho and para isomers relative to the nitro group with a high yield (95-86%). 2-Nitroquinoline does not undergo vicarious amination but displacement of the labile nitro group by an amino group occurs and then transformation to an imine compound and hydrolysis gives 2(1H)-quinolinone.

Nitroarylamines via the Vicarious Nucleophilic Substitution of Hydrogen: Amination, Alkylamination, and Arylamination of Nitroarenes with Sulfenamides

A new reaction of sulfenamides with electrophilic arenes under basic conditions is described. The σ adducts formed from nitroarenes and the anions of sulfenamides undergo elimination of thiol to produce the corresponding o- and/or p-nitroanilines. This reaction is analogous to the known alkylation and hydroxylation of nitroarenes via the vicarious nucleophilic substitution of hydrogen (VNS). The reaction gives access to a wide range of substituted nitroanilines, nitronaphthylamines, and aminoheterocycles. By means of the reaction with N-alkyl- and N-arylsulfenamides, it is possible to obtain N-alkylnitroanilines and nitrodiarylamines. By varying the structure of sulfenamide and the reaction conditions, particularly the nature and concentration of the base, it is possible to control the orientation of animation.

SYNTHESIS AND BIOLOGICAL ACTIVITY OF 2-MERCAPTO-1H-IMIDAZOQUINOLINE DERIVATIVES

5,6-Diaminoquinoline (1c) which was prepared from 6-nitroquinoline (1a) by successive amination and reduction, upon condensation with carbondisulphide in alkaline medium yielded 2-mercapto-1H-imidazoquinoline (IIa).This on treatment with alkyl, aralkyl and acid halides gave the corresponding thioethers (II b-i) and thioesters (II j,k) respectively.Their structures were established by elemental analysis and spectral data (I.R., P.M.R., 13C N.M.R. and mass).The biological activity of some of the compounds was evaluated.