ChemicalBook > Product Catalog >Pharmaceutical intermediates >Heterocyclic compound >Quinoline compounds >4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

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

4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline Structure
CAS No.
99010-64-7
Chemical Name:
4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline
Synonyms
cas 99010-64-7;Imiquimod USP RC C;Imiquimod Impurity-C;DesaMino ChloroiMiquiMod;1H-Imidazo[4,5-c]quinoline,;IMiquiMod Related CoMpound C;Imiquimod USP Related Compound C;4-Chloro-1-isobutyl-1H-imidazo[4,5-;1H-IMIDAZO[4,5-C]QUINOLINE, 4-CHLORO-1-(;4-CHLORO-1-ISOBUTYL-1H-IMIBENZO(4,5-C)QUINOLINE
CBNumber:
CB6449735
Molecular Formula:
C14H14ClN3
Molecular Weight:
259.73
MOL File:
99010-64-7.mol
Modify Date:
2024/1/9 10:21:27

4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline 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
CAS DataBase Reference 99010-64-7(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338
HS Code  2934990002

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

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

4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline Preparation Products And Raw materials

Raw materials

Preparation Products

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4-CHLORO-1-(2-METHYLPROPYL)-1H-IMIDAZO[4,5-C]QUINOLINE 4-CHLORO-1-ISOBUTYL-1H-IMIDAZOBEN[4,5-C]QUINOLINE 1-[2-METHYLPROPYL]-1H-2-CHLOROIMIDAZO-[4,5-C]QUINOLINE 1H-IMIDAZO[4,5-C]QUINOLINE, 4-CHLORO-1-(2-METHYLPROPYL) 4-Chloro-1-(2-methylpropyl)-1H-imidazo-(4,5c)quinolinone 2-CHLORO-1-(2-METHYLPROPYL)-1H-IMIDAZO[4,5-C]QUINOLINONE 1H-Imidazo[4,5-c]quinoline, 4-CHLORO-1-ISOBUTYL-1H-IMIBENZO(4,5-C)QUINOLINE 1H-Imidazo[4,5-c]quinoline, -chloro-1-(2-methylpropyl)- 1H-Imidazo[4,5-c]quinolinone,2-chloro-1-(2-methylpropyl) Imiquimod Related Compound C (25 mg) (4-Chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline) 1-H-IMIDAZO[4,5-C]QUINOLINONE,4-CHLORO-1-(2-METHYL PROPYL) IMiquiMod Related CoMpound C DesaMino ChloroiMiquiMod 4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline###4-Chloro-1-(2-methylpropyl)-1H-imidazole[4,5-c]quinoline 1H-IMIDAZO[4,5-C]QUINOLINE, 4-CHLORO-1-( 4-chloro-1-(2-methylpropyl)imidazo[4,5-c]quinoline Imiquimod USP Related Compound C 4-Chloro-1-isobutyl-1H-imidazo[4,5- Imiquimod USP RC C Imiquimod Impurity 3 (Imiquimod Related Compound C) Imiquimod Impurity-C Imiquimod Related Compound C (4-Chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline) (1338346) 4-CHLORO-1-ISOBUTYL-1H-IMIDAZO (4,5'D)QUINOLINE cas 99010-64-7 99010-64-7 C14H14ClN3 Quinolines, Quinazolines and derivatives Intermediates of Imiquimod API intermediates