4-CHLORO-2-METHYLQUINOLINE Chemical Properties

Melting point:

39 °C

Boiling point:

269-270 °C (lit.)

Density 

0.881 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.622(lit.)

Flash point:

>230 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder to lump to clear liquid

pka

4.40±0.50(Predicted)

color 

White or Colorless to Yellow

Water Solubility 

Slightly soluble in water.

BRN 

3522

InChI

InChI=1S/C10H8ClN/c1-7-6-9(11)8-4-2-3-5-10(8)12-7/h2-6H,1H3

InChIKey

HQAIROMRVBVWSK-UHFFFAOYSA-N

SMILES

N1C2C(=CC=CC=2)C(Cl)=CC=1C

CAS DataBase Reference

4295-06-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

2933499090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-CHLORO-2-METHYLQUINOLINE Usage And Synthesis

Chemical Properties

Melting point 42-43℃, boiling point 269-270℃, 83℃ (93Pa), relative density 0.881, refractive index 1.6224. Slightly soluble in water.

Uses

4-Chloroquinaldine is used in the preparation of 4-phenyl-hydrazinoquinaldine

Synthesis

General procedure: 4-hydroxy-2-methylquinoline (5a-c) was added to POCl3 and the reaction mixture was heated to reflux for 12 hours. Upon completion of the reaction, the excess POCl3 was removed by distillation under reduced pressure. the residue was washed once and twice each with CHCl3 and toluene sequentially. The solid obtained was dissolved in CH2Cl2 and triethylamine was added dropwise until the pH of the aqueous wash solution was greater than 10. Finally, the reaction mixture was filtered to afford the target products 2-methyl-4-chloroquinoline (6a-c).

References

[1] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 1114 - 1125
[2] Patent: US2008/171765, 2008, A1. Location in patent: Page/Page column 19-20
[3] Australian Journal of Chemistry, 2003, vol. 56, # 1, p. 39 - 44
[4] Letters in Drug Design and Discovery, 2018, vol. 15, # 9, p. 937 - 944
[5] Patent: WO2018/178277, 2018, A1. Location in patent: Paragraph 00114

4-CHLORO-2-METHYLQUINOLINE(4295-06-1)Related Product Information

• 6-(BROMOMETHYL)-4-CHLORO-2-(TRIFLUOROMETHYL)-QUINOLINE
• 2-METHYL-4,6,8-TRICHLOROQUINOLINE
• 4-CHLORO-6-METHYL-2-(TRIFLUOROMETHYL)QUINOLINE
• 6-Methoxy-4-chloro-2-methylquinoline
• 4-CHLOROQUINALDINE HCL
• 4-CHLORO-2-METHYLQUINOLINE
• 2-METHYL-4,7,8-TRICHLOROQUINOLINE
• 6-BROMO-4-CHLORO-2-(TRIFLUOROMETHYL)QUINOLINE
• 2,8-BIS(TRIFLUOROMETHYL)-4-CHLOROQUINOLINE
• 4-CHLORO-2-(TRIFLUOROMETHYL)QUINOLINE
• 4-CHLORO-2-PHENYLQUINOLINE, 99
• 8-CHLORO-5-METHYLQUINOLINE
• 5-Chloroquinaldine
• 2-Chloro-4-methylquinoline, 2-Chlorolepidine
• 2-CHLORO-6-METHYLQUINOLINE CARBOXALDEHYDE
• ethyl 4-chloro-2-methylquinoline-6-carboxylate
• 6,7-DICHLOROQUINALDINE
• 7-CHLORO-3-METHYLQUINOLINE-8-CARBOXYLICACID