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261769

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

261769-25G:
261769-VAR:
261769-5G:
261769-BULK:

Certificates of Analysis (COA)

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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
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)
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.
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
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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