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HomeProduct name list4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

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

Synonym(s):4-Chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline;NSC 672965

  • CAS NO.:99010-64-7
  • Empirical Formula: C14H14ClN3
  • Molecular Weight: 259.73
  • MDL number: MFCD06658174
  • EINECS: 619-386-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-01-09 10:21:27
4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline Structural

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

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.

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

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

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

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

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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

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