ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Quinoline compounds 4-methylquinoline

4-methylquinoline

Product Name4-methylquinoline
CAS491-35-0
MFC10H9N
MW143.19
EINECS207-734-2
MOL File491-35-0.mol

Chemical Properties

Melting point	9-10 °C(lit.)
Boiling point	261-263 °C(lit.)
Density	1.083 g/mL at 25 °C(lit.)
refractive index	n20/D 1.620(lit.)
Flash point	>230 °F
storage temp.	Refrigerator
solubility	Slightly soluble in water, miscible with alcohol and oils.
pka	5.67(at 20℃)
form	Liquid
color	Pale Orange
Odor	at 100.00 %. burnt oily herbal floral sweet
Odor Type	burnt
biological source	synthetic
Water Solubility	Slightly soluble
Sensitive	Light Sensitive
Merck	14,5441
BRN	110926
Henry's Law Constant	1.3×10¹ mol/(m³Pa) at 25℃, HSDB (2015)
Cosmetics Ingredients Functions	PERFUMING
InChI	1S/C10H9N/c1-8-6-7-11-10-5-3-2-4-9(8)10/h2-7H,1H3
InChIKey	MUDSDYNRBDKLGK-UHFFFAOYSA-N
SMILES	Cc1ccnc2ccccc12
LogP	2.610
CAS DataBase Reference	491-35-0(CAS DataBase Reference)
NIST Chemistry Reference	Quinoline, 4-methyl-(491-35-0)
EPA Substance Registry System	Quinoline, 4-methyl- (491-35-0)

Safety Information

Hazard Codes	Xi,Xn
Risk Statements	36/37/38-68-40
Safety Statements	26-36-45-36/37/39-22
WGK Germany	3
RTECS	OH0316000
F	8-10
TSCA	TSCA listed
HS Code	29334900
Storage Class	10 - Combustible liquids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3
Hazardous Substances Data	491-35-0(Hazardous Substances Data)

MSDS

Provider	Language
Lepidine	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Description

Refer to 6-METHYLQUINOLINE.

Chemical Properties

clear slightly yellow to brown liquid

Physical properties

4-Methylquinoline is a colorless liquid with a weak quinoline-like odor. It is slightly soluble in water, miscible with many organic solvents, and volatile in steam.

Uses

4-Methylquinoline is used as a reagent in the synthesis of azetidine based ene-amides as potent bacterial enoyl ACP reductase inhibitors. Also used as a reagent in the synthesis of cyanine-styryl dyes with enhanced photostability for fluorescent DNA imaging.

Uses

4-methylquinoline is used mainly in flavor compositions for imitation Honey, Nut, Butter, Caramel, etc. and in certain fruit complexes. The concentration used is normally about 0.2 to 2 ppm in the finished product.

Definition

ChEBI: A methylquinoline carrying a methyl substituent at position 4.

Production Methods

4-Methylquinoline can be recovered from the highest-boiling fraction of the coal-tar quinoline bases via its o-cresol addition compound. It can be synthesized by condensation of aniline and methyl vinyl ketone.

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 5291, 1987 DOI: 10.1016/S0040-4039(00)96710-8

General Description

Synthesis of lepidine from 4-anilinobutan-2-one in ethanol in the presence of HCl or FeCl₃has been reported. Nitration of lepidine has been reported.

Purification Methods

Reflux lepidine with BaO, then fractionally distil it. Further purify it via its recrystallised dichromate salt (m 138o) (from H2O). [Cumper et al. J Chem Soc 1176 1962.] [Beilstein 20 III/IV 3477, 20/7 V 389.]

4-methylquinoline

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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