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H43806

Sigma-Aldrich

4-Hydroxy-2-methylquinoline

98.5%

Synonym(s):

2-Methyl-4-quinolinol

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About This Item

Empirical Formula (Hill Notation):
C10H9NO
CAS Number:
Molecular Weight:
159.18
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

98.5%

SMILES string

Cc1cc(O)c2ccccc2n1

InChI

1S/C10H9NO/c1-7-6-10(12)8-4-2-3-5-9(8)11-7/h2-6H,1H3,(H,11,12)

InChI key

NWINIEGDLHHNLH-UHFFFAOYSA-N

Application

4-Hydroxy-2-methylquinoline can be used as an intermediate in the synthesis of a wide range of medicinally important compounds such as:
  • Synthesis of 2-(quinolin-4-yloxy)acetamides as potent antitubercular agents.
  • Synthesis of 2-arylethenylquinoline derivatives for the treatment of Alzheimer′s disease.
  • Synthesis of 1,10-diethoxy-1H-pyrano[4,3-b]quinolones as antibacterial agents.
  • Synthesis of phenylimidazole-pyrazolo[1,5-c]quinazolines as potent phophodiesterase 10A (PDE10A) inhibitors.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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)

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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2-(Quinolin-4-yloxy) acetamides are active against drug-susceptible and drug-resistant Mycobacterium tuberculosis strains.
Pissinate K, et al.
ACS Medicinal Chemistry Letters, 7(3), 235-239 (2016)
Design, synthesis, and biological evaluation of 2-arylethenylquinoline derivatives as multifunctional agents for the treatment of Alzheimer's disease.
Wang X Q, et al.
European Journal of Medicinal Chemistry, 89, 349-361 (2015)
Quinaldine derivatives: Preparation and biological activity.
Jampilek J, et al.
Medicinal Chemistry, 1(6), 591-599 (2005)
Synthesis and SAR study of new phenylimidazole-pyrazolo [1, 5-c] quinazolines as potent phosphodiesterase 10A inhibitors.
Asproni B, et al.
Bioorganic & Medicinal Chemistry, 19(1), 642-649 (2011)
Synthesis of new 1, 10-diethoxy-1H-pyrano [4, 3-b] quinolines and their antibacterial studies.
Dhanabal T, et al.
Indian J. Chem. B, 45B(02) (2006)

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