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Sigma-Aldrich

8-Methylquinoline

97%

Synonym(s):

o-Toluquinoline

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About This Item

Empirical Formula (Hill Notation):
C10H9N
CAS Number:
611-32-5
Molecular Weight:
143.19
Beilstein:
111340
EC Number:
210-264-0
MDL number:
MFCD00006810
UNSPSC Code:
12352100
PubChem Substance ID:
24855833
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.614 (lit.)

bp

143 °C/34 mmHg (lit.)

mp

−80 °C (lit.)

density

1.052 g/mL at 25 °C (lit.)

SMILES string

Cc1cccc2cccnc12

InChI

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

InChI key

JRLTTZUODKEYDH-UHFFFAOYSA-N

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General description

Tumorigenic potential of 8-methylquinoline has been evaluated in newborn CD-1 mice and Sprague-Dawley rats.

Application

8-Methylquinoline has been used in preparation of osmium chloridophosphine complexes, as quinoline carbene tautomers.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

221.0 °F - closed cup

Flash Point(C)

105 °C - closed cup

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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R Yang et al.
Luminescence : the journal of biological and chemical luminescence, 16(2), 129-133 (2001-04-20)
8-Methylquinoline is unique among the monomethylquinolines in the red-shift it shows in the absorption band derived from the short axis polarized ((1)L(a) <-- (1)A) electronic transition, relative to that in quinoline itself. The effect is even more pronounced in the
Kami L Hull et al.
Journal of the American Chemical Society, 128(22), 7134-7135 (2006-06-01)
This communication describes the development of a new Pd-catalyzed method for the fluorination of carbon-hydrogen bonds. A key step of these transformations involves palladium-mediated carbon-fluorine coupling-a much sought after, but previously unprecedented, transformation. These reactions were successfully achieved under oxidative
Kate B McMurtrey et al.
Organic letters, 14(16), 4094-4097 (2012-08-01)
The palladium-catalyzed C-H fluorination of 8-methylquinoline derivatives with nucleophilic fluoride is reported. This transformation involves the use of AgF as the fluoride source in combination with a hypervalent iodine oxidant. Both the scope and mechanism of the reaction are discussed.
Synthetic routes to N-heterocyclic carbene complexes: pyridine-carbene tautomerizations.
Doris Kunz
Angewandte Chemie (International ed. in English), 46(19), 3405-3408 (2007-04-05)
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%
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