90-52-8

Basic information

• Product Name: 8-AMINO-6-METHOXYQUINOLINE
• Synonyms: 6-methoxy-8-aminoquinoline;6-methoxy-8-quinolinamin;6-methoxy-8-quinolinamine;6-methoxy-8-quinolylamine;8-amino-6-methoxy-quinolin;amichin;wr15081;IFLAB-BB F1901-0147
• CAS NO: 90-52-8
• Molecular Formula: C₁₀H₁₀N₂O
• Molecular Weight: 174.2
• EINECS: 202-001-3
• Product Categories: Quinoline;Quinoline&Isoquinoline;organic building block
• Mol File: 90-52-8.mol
• Article Data: 29

Chemical Properties

• Melting Point: 41 °C
• Boiling Point: 361.8 °C at 760 mmHg
• Flash Point: 172.6 °C
• Appearance: solid
• Density: 1.217 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.49±0.10(Predicted)
• Stability: Incompatible with strong oxidizing agents.
• CAS DataBase Reference: 8-AMINO-6-METHOXYQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-AMINO-6-METHOXYQUINOLINE(90-52-8)
• EPA Substance Registry System: 8-AMINO-6-METHOXYQUINOLINE(90-52-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 90-52-8(Hazardous Substances Data)

Usage

Chemical Properties

solid

Uses

8-Amino-6-methoxyquinoline has oxidizing properties as well as potential anti-tuberculosis application with its antimycobacterial messages as well.

Purification Methods

Distil it under N2 and at high vacuum, then recrystallise it several times from MeOH (0.4mL/g). It remains colourless for several months when purified in this way [Elderfield & Rubin J Am Chem Soc 75 2963 1953]. The hydrobromide [312693-53-1] M 255.1 has m 238o(dec). [Beilstein 22 III/IV 5934.]

InChI:InChI=1/C10H10N2O/c1-13-8-5-7-3-2-4-12-10(7)9(11)6-8/h2-6H,11H2,1H3

Upstream product

• 96-96-8 4-methoxy-2-nitroaniline 
• 85-81-4 6-methoxy-8-nitroquinoline 
• 90771-32-7 2-methoxy-8-nitroquinoline 
• 90-34-6 Primaquine 
• 63457-03-4 4-Chloro-6-methoxy-8-nitroquinoline 
• 23432-47-5 4-hydroxy-6-methoxy-8-nitroquinoline 
• 25165-69-9 5-(((4-methoxy-2-nitrophenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 51-66-1 4-methoxyacetanilide 
• 104-94-9 4-methoxy-aniline 
• 119-81-3 4-methoxy-2-nitroacetanilide 
• 4280-28-8 3,4-dinitroanisole 
• 59353-69-4 (6-methoxy-[8]quinolyl)-carbamic acid ethyl ester 
• 79325-89-6 4-methoxy-2-methyl-3-oxo(1H)-2,3-dihydropyrrolo<5,4-h>quinoline 
• 74-88-4 methyl iodide 

Downstream Products

• 90-34-6 Primaquine 
• 796851-15-5 8-chloro-6-methoxyquinoline 
• 282547-70-0 8-(4-benzyl-piperazin-1-yl)-6-methoxy-quinoline 
• 19401-75-3 N-(6-methoxyquinolin-8-yl)benzamide 
• 857949-65-6 N-(N-acetyl-sulfanilyl)-N',N'-diethyl-N-(6-methoxy-[8]quinolyl)-ethylenediamine 
• 408536-52-7 6-methoxy-quinoline-8-carboxylic acid 
• 7148-88-1 5-bromo-6-methoxy-8-aminoquinoline 
• 5396-19-0 5-chloro-6-methoxy-[8]quinolylamine 
• 159925-99-2 8-bromoquinolin-6-ol 
• 7404-14-0 NSC 403439-F 
• 94453-52-8 4-amino-5-carboxamido-3-(6-methoxy-8-quinolyl)-1-methylimidazolium toluene-p-sulphonate 
• 88609-36-3 7-amino-8-cyclohexylamine-6-methoxyquinoline 
• 102096-41-3 (S)-2-Amino-N-[(S)-1-(6-methoxy-quinolin-8-ylcarbamoyl)-ethyl]-3-phenyl-propionamide; hydrobromide 
• 102096-43-5 (S)-N¹-[(S)-2-(6-Methoxy-quinolin-8-ylamino)-1-methyl-ethyl]-3-phenyl-propane-1,2-diamine; hydrochloride 

Relevant articles and documents

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8-amino-6-methoxyquinoline—tetrazole hybrids: Impact of linkers on antiplasmodial activity

A new series of compounds was prepared from 6-methoxyquinolin-8-amine or its N-(2-aminoethyl) analogue via Ugi-azide reaction. Their linkers between the quinoline and the tert-butyltetrazole moieties differ in chain length, basicity and substitution. Compounds were tested for their antiplasmodial activity against Plasmodium falciparum NF54 as well as their cytotoxicity against L-6-cells. The activity and the cytotoxicity were strongly influenced by the linker and its substitution. The most active compounds showed good activity and promising selectivity.

Minimization of Back-Electron Transfer Enables the Elusive sp3 C?H Functionalization of Secondary Anilines

Anilines are some of the most used class of substrates for application in photoinduced electron transfer. N,N-Dialkyl-derivatives enable radical generation α to the N-atom by oxidation followed by deprotonation. This approach is however elusive to monosubstituted anilines owing to fast back-electron transfer (BET). Here we demonstrate that BET can be minimised by using photoredox catalysis in the presence of an exogenous alkylamine. This approach synergistically aids aniline SET oxidation and then accelerates the following deprotonation. In this way, the generation of α-anilinoalkyl radicals is now possible and these species can be used in a general sense to achieve divergent sp3 C?H functionalization.