4-methylquinoline 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 

Chloroform (Slightly), Methanol (Slightly)

pka

5.67(at 20℃)

form 

Liquid

color 

Pale Orange

Odor

at 100.00 %. burnt oily herbal floral sweet

Odor Type

burnt

Water Solubility 

Slightly soluble

Sensitive 

Light Sensitive

Merck 

14,5441

BRN 

110926

InChIKey

MUDSDYNRBDKLGK-UHFFFAOYSA-N

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 

Yes

HS Code 

29334900

Hazardous Substances Data

491-35-0(Hazardous Substances Data)

MSDS

• Language:English Provider:Lepidine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-methylquinoline 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

Lepidine is used in the preparation of certain dyes.

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.

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.

Definition

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

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 FeCl₃ has 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(491-35-0)Related Product Information

• 8-Hydroxyquinoline
• quinolinium hydrogen sulphate
• Ethoxyquin
• 8-Methylquinoline
• Quinclorac
• Isoquinoline
• 2-HYDROXY-4-METHYLQUINOLINE
• 6-Hydroxy-2(1H)-3,4-dihydroquinolinone
• Quinhydrone
• CINCHOPHEN
• 1,1'-DIETHYL-4,4'-CARBOCYANINE IODIDE
• QUINOLINE-4-CARBOXYLIC ACID
• Lepidine, 2-chloro-
• Bathophenanthroline
• 2,4-DIMETHYLQUINOLINE
• BATHOPHENANTHROLINEDISULFONIC ACID DISODIUM SALT TRIHYDRATE
• 3,4,7,8-Tetramethyl-1,10-phenanthroline
• 4,7-Dimethyl-1,10-phenanthroline