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206571

Sigma-Aldrich

6-Methoxy-8-nitroquinoline

99%

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About This Item

Empirical Formula (Hill Notation):
C10H8N2O3
CAS Number:
85-81-4
Molecular Weight:
204.18
EC Number:
201-633-7
MDL number:
MFCD00006802
UNSPSC Code:
12352100
PubChem Substance ID:
24852410
NACRES:
NA.22

Assay

99%

form

powder

mp

158-160 °C (lit.)

SMILES string

COc1cc([N+]([O-])=O)c2ncccc2c1

InChI

1S/C10H8N2O3/c1-15-8-5-7-3-2-4-11-10(7)9(6-8)12(13)14/h2-6H,1H3

InChI key

MIMUSZHMZBJBPO-UHFFFAOYSA-N

Application

6-Methoxy-8-nitroquinoline was used in the synthesis of:
  • 6-methoxy-8-aminoquinoline, metabolite of primaquine
  • 6-methoxy-8-hydroxylaminoquinoline
  • 2-substituted/2,5-disubstituted-6-methoxy-8-nitroquinolines

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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)

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Suryanarayana Vangapandu et al.
Bioorganic & medicinal chemistry, 12(10), 2501-2508 (2004-04-28)
We report in vitro antimycobacterial properties of ring-substituted quinolines (series 1-4) constituting 56 analogues against drug-sensitive and drug-resistant M. tuberculosis H37Rv strains. The most effective compounds 2h (R1 = R2 = c-C6H11, R3 = NO2, series 1) and 13g (R1
L J Bolchoz et al.
The Journal of pharmacology and experimental therapeutics, 297(2), 509-515 (2001-04-17)
Primaquine is an important antimalarial agent because of its activity against exoerythrocytic forms of Plasmodium spp. However, methemoglobinemia and hemolytic anemia are dose-limiting side effects of primaquine therapy that limit its efficacy. These hemotoxicities are thought to be mediated by

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