| Identification | More | [Name]
8-Aminoquinoline | [CAS]
578-66-5 | [Synonyms]
8-AMINOQUINOLINE
8-QUINOLINAMINE
8-QUINOLYLAMINE
AKOS 91147
AKOS AUF01700
ASISCHEM Z74664
QUINOLIN-8-AMINE
TIMTEC-BB SBB004126
8-amino-quinolin
nc066
Quinoline, 8-amino-
wr6920
8-Aminoquinoline,98%
8-Amino
8-Quinolinylamine | [EINECS(EC#)]
209-427-9 | [Molecular Formula]
C9H8N2 | [MDL Number]
MFCD00006809 | [Molecular Weight]
144.17 | [MOL File]
578-66-5.mol |
| Chemical Properties | Back Directory | [Appearance]
green to beige-brown crystalline powder | [Melting point ]
60-65 °C (lit.) | [Boiling point ]
174 °C/26 mmHg (lit.) | [density ]
1.1148 (estimate) | [refractive index ]
1.7080 (estimate) | [Fp ]
174°C/26mm | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
Crystalline Powder | [pka]
pK1: 3.99(+1) (20°C,μ=0.01) | [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) | [Storage Precautions]
Store under nitrogen | [EPA Substance Registry System]
8-Quinolinamine (578-66-5) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R68:Possible risk of irreversible effects.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/38:Irritating to eyes and skin . | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S22:Do not breathe dust .
S36:Wear suitable protective clothing . | [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 |
| Hazard Information | Back Directory | [Chemical Properties]
green to beige-brown crystalline powder | [Uses]
8-Aminoquinoline has been used in:
preparation of base-stabilized terminal borylene complex of osmium
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. | [reaction suitability]
reaction type: C-H Activation
reagent type: catalyst | [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.] |
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