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108928

Sigma-Aldrich

6-Methylquinoline

98%

Synonym(s):

p-Toluquinoline, NSC 4152

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About This Item

Empirical Formula (Hill Notation):
C10H9N
CAS Number:
91-62-3
Molecular Weight:
143.19
Beilstein:
110336
EC Number:
202-084-6
MDL number:
MFCD00006804
UNSPSC Code:
12352100
eCl@ss:
39180204
PubChem Substance ID:
24846839
NACRES:
NA.22

vapor density

>1 (vs air)

Assay

98%

refractive index

n20/D 1.614 (lit.)

bp

256-260 °C (lit.)

density

1.067 g/mL at 20 °C (lit.)

SMILES string

Cc1ccc2ncccc2c1

InChI

1S/C10H9N/c1-8-4-5-10-9(7-8)3-2-6-11-10/h2-7H,1H3

InChI key

LUYISICIYVKBTA-UHFFFAOYSA-N

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Application

6-Methylquinoline can be used as primary carbon source in culture of Pseudomonas putida QP1. 6-Methylquinoline was used in the synthesis of fluorescent halide-sensitive quinolinium dyes and fluorescent probes for determination of chloride in biological systems.

Biochem/physiol Actions

6-Methylquinoline undergoes biodegradation by quinoline-degrading culture of Pseudomonas putida.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315

Hazard Classifications

Acute Tox. 4 Oral - Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Chloride sensitive probes for biological applications.
Geddes CD, et al.
Dyes and Pigments, 48(3), 227-231 (2001)
S Rothenburger et al.
Applied and environmental microbiology, 59(7), 2139-2144 (1993-07-01)
Selective culturing of pseudomonads that could degrade quinoline led to enrichment cultures and pure cultures with expanded substrate utilization and transformation capabilities for substituted quinolines in immobilized and batch cultures. Immobilized cells of the pseudomonad cultures rapidly transformed quinolines to
C E Scharping et al.
Carcinogenesis, 14(5), 1041-1047 (1993-05-01)
The hepatic microsomal metabolism of the carcinogenic 8-methylquinoline (8MQ) and its noncarcinogenic isomer, 6-methylquinoline (6MQ), were compared for preparations from control rats and rats pretreated with phenobarbital or 3-methylcholanthrene. For each compound the alcohol was the major metabolite, constituting 50-75%
Umar Farooq Rizvi et al.
Acta crystallographica. Section C, Crystal structure communications, 64(Pt 10), o547-o549 (2008-10-08)
Molecules of (E)-3-(2-chloro-6-methylquinolin-3-yl)-1-(5-iodo-2-thienyl)prop-2-en-1-one, C(17)H(11)ClINOS, (I), and (E)-3-(2-chloro-6-methylquinolin-3-yl)-1-(5-methyl-2-furyl)prop-2-en-1-one, C(18)H(14)ClNO(2), (II), adopt conformations slightly twisted from coplanarity. Both structures are devoid of classical hydrogen bonds. However, nonclassical C-H...O/N interactions [with C...O = 3.146 (5) A and C...N = 3.487 (3) A] link
C D Geddes et al.
Analytical biochemistry, 293(1), 60-66 (2001-05-25)
Three fluorescent halide-sensitive quinolinium dyes have been produced by the reaction of the 6-methylquinoline heterocyclic nitrogen base with methyl bromide, methyl iodide, and 3-bromo-1-propanol. The quaternary salts, unlike the precursor molecule, are readily water soluble and the fluorescence intensity of

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