5-Amino-8-quinolinol dihydrochloride Chemical Properties

Melting point:

279 °C (dec.)(lit.)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

color 

Orange to Amber to Dark red

Water Solubility 

almost transparency

InChI

1S/C9H8N2O.2ClH/c10-7-3-4-8(12)9-6(7)2-1-5-11-9;;/h1-5,12H,10H2;2*1H

InChIKey

VTQDJAUGGZFPOI-UHFFFAOYSA-N

SMILES

Cl[H].Cl[H].Nc1ccc(O)c2ncccc12

CAS DataBase Reference

21302-43-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

HS Code 

29334990

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:SigmaAldrich

5-Amino-8-quinolinol dihydrochloride Usage And Synthesis

Chemical Properties

Crystalline powder

Uses

5-Amino-8-hydroxyquinoline dihydrochloride was used in synthesis of:

• 5-acetamido-8-hydroxyquinoline hydrochloride
• 5-(p-tolylsulfonylimino)quinolin-8-one
• 5,8-quinolinesemiquinone via ferric chloride oxidation

Synthesis

Step 1: Preparation of 5-nitroso-8-hydroxyquinoline hydrochloride

A solution of NaNO2 (30 g) in water (100 ml) was added to a mixture of 8-hydroxyquinoline (58 g, 0.4 mol) in distilled water, concentrated hydrochloric acid (75 ml) and ice (200 g) at 0-4??C. The reaction mixture was kept at 0??C overnight. Within 1 hr ?? C. The reaction mixture was kept at 0?? C. overnight and then filtered by washing with cold water to give 5-nitroso-8-hydroxyquinoline hydrochloride (95%).

Step 2: Preparation of 5-amino-8-hydroxyquinoline dihydrochloride

5-Nitroso-8-hydroxyquinoline chloride (40 g) was added to a mixture of water (160 ml) and 5N-NaOH (260 ml) and heated to 40??C. Na2S2O4 (95 g) was added to the reaction mixture and the temperature was raised to 75-80??C. The reaction mixture was cooled to 50??C and 12N-HCl (250 ml) was added. The reaction mixture was then cooled to 0 ??C and filtered to give 5-amino-8-hydroxyquinoline dihydrochloride (34 g, 69%).

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