8-Aminoquinoline Chemical Properties

Melting point:

60-65 °C (lit.)

Boiling point:

174 °C/26 mmHg (lit.)

Density 

1.1148 (estimate)

refractive index 

1.7080 (estimate)

Flash point:

174°C/26mm

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

pK1: 3.99(+1) (20°C,μ=0.01)

form 

Crystalline Powder

color 

Green to beige-brown

Water Solubility 

slightly soluble

Sensitive 

Air Sensitive

BRN 

114474

CAS DataBase Reference

578-66-5(CAS DataBase Reference)

NIST Chemistry Reference

8-Quinolinamine(578-66-5)

EPA Substance Registry System

8-Quinolinamine (578-66-5)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

68-36/37/38-20/21/22-36/38

Safety Statements 

36/37/39-26-22-36

RIDADR 

UN2811

WGK Germany 

3

RTECS 

VA9627000

Hazard Note 

Harmful/Irritant/Air Sensitive

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29334990

Toxicity

mmo-sat 50 mg/plate MUREAV 39,285,77

MSDS

• Language:English Provider:8-Quinolinamine
• Language:English Provider:ACROS
• Language:English Provider:ALFA

8-Aminoquinoline Usage And Synthesis

Chemical Properties

green to beige-brown crystalline powder

Uses

8-Aminoquinoline is used as pesticide and pharmaceutical intermediate. It has been used in the preparation of base-stabilized terminal borylene complex of osmium. It is also used in the spectrophotometric determination of bivalent palladium.

Preparation

Synthesis of 8-aminoquinoline: Under an ice bath, sulfuric acid (2.0 mL) was added onto quinoline (5 mmol, 1.0 equiv) then 65% nitric acid (3.0 equiv) were added dropwise and stirred for 4h at rt. The mixture was poured into the ice water and neutralized with NaOH; and then extracted with dichloromethane. After dried over Na2SO4 and evaporated in vacuo, used next step without purification.
Mixture of nitroquinolines and 5% Pd/C was solved in ethanol and suspension was saturated with hydrogen gas under atmospheric pressure at 40°C until the starting material was consumed. 2 h later, the mixture was filtered and evaporated. The crude product was purified by silica gel column chromatography, eluting with EtOAc in hexanes to yield the desired 8-aminoquinoline is isolated as a brown solid in a yield of 32%.
Obtained as a brown solid (231 mg, 32%); 1H NMR (500 MHz, CDCl3) δ 8.71 – 8.60 (m, 1H), 7.93 (d, J = 8.2 Hz, 1H), 7.29 – 7.16 (m, 2H), 7.02 (d, J = 8.1 Hz, 1H), 6.80 (d, J = 7.4 Hz, 1H), 4.89 (s, 2H).

General Description

8-Aminoquinoline fluoresce moderately to weakly in low dielectric media but not in strongly hydrogen-bonding or acidic aqueous media. The reaction of 8-aminoquinoline with chromium (III), manganese (II), iron (II) and (III), cobalt (II), nickel (II), copper (II), zinc (II), cadmium (II) and platinum (II) salts has been studied.

Safety Profile

Human mutation data reported.When heated to decomposition it emits toxic fumes ofNOx.

Purification Methods

8-Aminoquinoline crystallises from EtOH, ligroin, octane or H2O, and complexes with metals. [Beilstein 22 III/IV 4708, 22/10 V 316.]

8-Aminoquinoline(578-66-5)Related Product Information

• QUINOLINE SULPHATE
• 8-Hydroxyquinoline
• Ethoxyquin
• Isoquinoline
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• 6-Hydroxy-2(1H)-3,4-dihydroquinolinone
• Quinclorac
• 5-Aminoquinoline
• 4-(Trifluoromethyl)quinolin-2-amine
• 6-AMINOQUINOLINE-4-CARBOXYLIC ACID
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• 2-AMINO-4-METHYL-QUINOLINE-3-CARBONITRILE
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• 5-BROMO-QUINOLIN-8-YLAMINE HYDROCHLORIDE