4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline Chemical Properties

Melting point:

139-140 °C(Solv: isopropanol (67-63-0))

Boiling point:

427.5±48.0 °C(Predicted)

Density 

1.29±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Solid

pka

3.15±0.30(Predicted)

color 

White to Off-White

InChI

InChI=1S/C14H14ClN3/c1-9(2)7-18-8-16-12-13(18)10-5-3-4-6-11(10)17-14(12)15/h3-6,8-9H,7H2,1-2H3

InChIKey

RRCWSLBKLVBFQD-UHFFFAOYSA-N

SMILES

N1C2C(=CC=CC=2)C2N(CC(C)C)C=NC=2C=1Cl

CAS DataBase Reference

99010-64-7(CAS DataBase Reference)

Safety Information

HS Code 

2934990002

4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline Usage And Synthesis

Description

4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline is a chemical product that has been used as a photosynthetic activator in weed science and pest control. It has been shown to significantly increase the growth rate of wheat, soybean, and oilseed crops. It is also effective at controlling weeds by inhibiting their ability to produce chlorophyll, thereby preventing them from photosynthesizing. 4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline has also been shown to be an effective herbicide for agricultural use.

Uses

Desamino Chloroimiquimod (Imiquimod USP Related Compound C) is a pharmacologically active compound related to Imiquimod (I475000), an immune response modifier. It stimulates the production of Interferon-a.

Synthesis

4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline is prepared by the reaction of 2-chloro-N⁴-(2-methylpropyl)quinoline-3,4-diamine and orthoformic acid triethyl ester. The specific synthesis steps are as follows:
A suspension of 2-chloro-N4 -(2-methylpropyl)-3,4-quinolinediamine (35 g) and triethylorthoformate (52.3 g, 2.5 eq) was heated at 145° C. for 10 h, during which time ethanol was removed by distillation. The resulting mixture was cooled to room temperature and the solid was removed by filtration. The solid was dissolved in hydrochloric acid (100 mL, 4N). The resulting solution was added to a solution of sodium hydroxide. The precipitate was filtered and washed with water to afford the product 4-chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline in 92% yield.

References

[1] Patent: WO2006/70379, 2006, A1. Location in patent: Page/Page column 9-10
[2] Patent: WO2006/70408, 2006, A2. Location in patent: Page/Page column 7; 12-13

4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline(99010-64-7)Related Product Information

• 4-amino-alpha,alpha-dimethyl-1H-imidazo(4,5-c)quinolin-1-ethanol
• [99010-09-0], C13H17N3,215.30
• Imiquimod Related Compound B (25 mg) (1-Isobutyl-1H-imidazo[4,5-c]quinoline 5-oxide)
• Imiquimod Related Compound D (25 mg) (1-Propyl-1H-imidazo[4,5-c]quinolin-4-amine)
• Imiquimod
• Chloromethyl isopropyl carbonate
• Epichlorohydrin
• 1-Methylimidazole
• 3-Methyl-2-butanone
• Imiquimod Impurity 2
• Imiquimod Impurity 6
• Imiquimod Impurity 5
• 1-(2-METHYLPROPYL)-1H-IMIDAZO[4,5-C]QUINOLINE
• Difluorochloromethane
• Chloroacetic acid
• RESIQUIMOD
• 4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline
• 4-CHLORO-1-(2-METHYLPROPYL)-1H-IMIDAZO[4,5-C]QUINOLINE 98%MIN