944263-65-4

Basic information

• Product Name: Demiditraz
• Synonyms: demiditraz;2-[(1S)-1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole;deMiditraz listed;PF 3814927;(S)-2-(1-(2,3-diMethylphenyl)ethyl)-1H-iMidazole;demiditraz:2-((1s)-1-(2,3-dimethylphenyl)ethyl)-1h-IMIDAZOLE
• CAS NO: 944263-65-4
• Molecular Formula: C13H16N2
• Molecular Weight: 200.28
• Mol File: 944263-65-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 407.3 °C at 760 mmHg
• Flash Point: 212.2 °C
• Appearance: /
• Density: 1.053
• CAS DataBase Reference: Demiditraz(CAS DataBase Reference)
• NIST Chemistry Reference: Demiditraz(944263-65-4)
• EPA Substance Registry System: Demiditraz(944263-65-4)

Safety Data

• Hazardous Substances Data: 944263-65-4(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
Demitidraz is used as an insecticide and pesticide for its broad-spectrum control of various pests that can damage crops and reduce agricultural productivity. Its effectiveness in controlling pests makes it a valuable tool in protecting crops from infestations.
Used in Pest Control:
Demitidraz is used as an acaricide for its ability to kill mites and ticks, which can be harmful to both crops and livestock. Its use in pest control helps to maintain the health of agricultural ecosystems and prevent the spread of diseases carried by these pests.

Synthetic route

demiditraz racemate (944263-08-5) → 2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (944263-65-4)

Conditions	Yield
In ethanol Purification / work up;

2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (944263-65-4) + methyl iodide (74-88-4) → 2-[(1S)-1-(2,3-Dimethylphenyl)ethyl]-1-methyl-1H-imidazole

Conditions	Yield
With caesium carbonate In acetone at 20℃; for 4h;

phosgene (75-44-5) + 2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (944263-65-4) → C14H15ClN2O

Conditions	Yield
With pyridine In dichloromethane; toluene at 0℃; for 0.333333h;

2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (944263-65-4) + trichloromethyl chloroformate (503-38-8) → C15H15Cl3N2O2

Conditions	Yield
With pyridine In acetonitrile at 0 - 20℃; for 0.166667 - 0.5h; Product distribution / selectivity;

2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (944263-65-4) + benzyl chloroformate (501-53-1) → Benzyl 2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole-1-carboxylate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 3h;

2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (944263-65-4) + 1,1,1-trifluoro-3-iodopropane (460-37-7) → 2-[(1S)-1-(2,3-Dimethylphenyl)ethyl]-1-(3,3,3-trifluoropropyl)-1H-imidazole

Conditions	Yield
With caesium carbonate In acetonitrile at 100℃; for 0.75h; Microwave irradiation;

2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (944263-65-4) + isobutyl chloroformate (543-27-1) → Isobutyl 2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole-1-carboxylate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 18h;

2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (944263-65-4) + 3-benzyloxybenzyl bromide (1700-31-8) → 1-[3-(Benzyloxy)benzyl]-2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole

Conditions	Yield
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 20℃; for 48h;

2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (944263-65-4) + Chloromethyl pivalate (18997-19-8) → {2-[(1S)-1-(2,3-Dimethylphenyl)ethyl]-1H-imidazol-1-yl}methyl pivalate

Conditions	Yield
With caesium carbonate In acetone at 20℃; for 18h;

1-(4-(bromomethyl)phenyl)-1H-1,2,4-triazole + 2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (944263-65-4) → 1-[4-({2-[(1S)-1-(2,3-Dimethylphenyl)ethyl]-1H-imidazol-1-yl}methyl)phenyl]-1H-1,2,4-triazole

Conditions	Yield
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 20℃; for 18h;

Upstream product

• 944263-08-5 demiditraz racemate 

Relevant articles and documents

SUBSTITUTED IMIDAZOLE COMBINATIONS

This invention relates to a composition comprising a combination of a) an alpha substituted 2-benzyl substituted imidazole and b) a 1-N-arylpyrazole, and optionally c) an insect growth regulator, and their use as a parasiticide in mammals.

SUBSTITUTED IMIDAZOLES

This invention relates to a range of alpha substituted 2-benzyl substituted imidazole compounds and pharmaceutically acceptable salts and solvates thereof, to compositions comprising such compounds, processes for their synthesis and their use as parasiticides.