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Sigma-Aldrich

8-Aminoquinoline

98%

Synonym(s):

8-Quinolinamine

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About This Item

Empirical Formula (Hill Notation):
C9H8N2
CAS Number:
578-66-5
Molecular Weight:
144.17
Beilstein:
114474
EC Number:
209-427-9
MDL number:
MFCD00006809
UNSPSC Code:
12352100
PubChem Substance ID:
24855768
NACRES:
NA.22

Quality Level

100

Assay

98%

form

solid

reaction suitability

reaction type: C-H Activation
reagent type: catalyst

bp

174 °C/26 mmHg (lit.)

mp

60-65 °C (lit.)

SMILES string

Nc1cccc2cccnc12

InChI

1S/C9H8N2/c10-8-5-1-3-7-4-2-6-11-9(7)8/h1-6H,10H2

InChI key

WREVVZMUNPAPOV-UHFFFAOYSA-N

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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.

Application

8-Aminoquinoline has been used in:
  • preparation of base-stabilized terminal borylene complex of osmium
  • spectrophotometric determination of bivalent palladium

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

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Kyalo Stephen Kanyiva et al.
Organic letters, 16(7), 1968-1971 (2014-03-22)
A palladium-catalyzed regioselective activation of C(sp(2))-H and C(sp(3))-H bonds of benzamides and carboxamides, followed by coupling with disilanes to afford organosilanes in moderate to high yields, with the aid of 8-aminoquinoline as a directing group, is reported. Catalytic C(sp(2))-H germanylation
Some transition metal complexes of 8-aminoquinoline.
Fanning JC and Taylor LT.
J. Inorg. Nucl. Chem., 27(10), 2217-2223 (1965)
Luis Carvalho et al.
Antimicrobial agents and chemotherapy, 55(9), 4204-4210 (2011-06-15)
The 8-aminoquinoline analogue sitamaquine (SQ) is an oral antileishmanial drug currently undergoing phase 2b clinical trials for the treatment of visceral leishmaniasis. In the present study, we investigated the mechanism of action of this drug in Leishmania donovani promastigotes. SQ
Hla Y Myint et al.
The American journal of tropical medicine and hygiene, 85(6), 1010-1014 (2011-12-07)
Because 8-aminoquinolines affect critical survival stages of Plasmodium parasites, treatment and control of malaria could be markedly improved by more widespread use of these drugs; however, hemolytic toxicity, which is widely prevalent in G6PD-deficient patients, severely constrains this use. Primaquine
José M Pérez-Victoria et al.
Antimicrobial agents and chemotherapy, 55(8), 3838-3844 (2011-06-08)
Although oral miltefosine represented an important therapeutic advance in the treatment of leishmaniasis, the appearance of resistance remains a serious threat. LMDR1/LABCB4, a P-glycoprotein-like transporter included in the Leishmania ABC (ATP-binding cassette) family, was the first molecule shown to be
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