13414-55-6

Usage

Uses

Used in Pesticide Industry:
2,3-Dihydro-2,2-dimethyl-7-nitrobenzofuran is used as a systemic insecticide, acaricide, and nematocide for controlling pests in various agricultural applications. Its presence in Carbofuran contributes to the overall effectiveness of the pesticide in managing insect, mite, and nematode populations.
Used in Pesticide Detection:
2,3-Dihydro-2,2-dimethyl-7-nitrobenzofuran is also utilized in the detection and analysis of pesticides, particularly Carbofuran. Its identification in samples can help in monitoring the presence and concentration of Carbofuran and related compounds in the environment, ensuring safety and compliance with regulatory standards.

InChI:InChI=1/C10H11NO3/c1-10(2)6-7-4-3-5-8(11(12)13)9(7)14-10/h3-5H,6H2,1-2H3

Upstream product

• 13414-54-5 2-[(2-methyl-2-propenyl)oxy]-1-nitrobenzene 

Downstream Products

• 68298-46-4 2,3-dihydro-2,2-dimethyl-7-aminobenzofuran 
• 64061-59-2 2-isobutenyl-6-nitrophenol 

Relevant academic research and scientific papers

Potent inhibitors of Acyl-CoA:cholesterol acyltransferase. 2. Structure- activity relationships of novel N-(2,2-dimethyl-2,3-dihydrobenzofuran-7- yl)amides

Novel N-(2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)amide derivatives 1 were synthesized and tested for their ability to inhibit rabbit small intestinal ACAT (acyl-CoA:cholesterol acyltransferase) and lower serum total cholesterol in cholesterol-fed rats. Among the synthesized compounds, N-(2,2,4,6- tetramethyl-2,3-dihydrobenzofuran-7-yl)amide derivatives showed potent ACAT inhibitory activity. The synthesis and structure-activity relationships of these compounds are described. A methyl group at position 6 of the 2,3- dihydrobenzofuran moiety was important for potent ACAT inhibitory activity. In the series of N-(2,2,4,6-tetramethyl-2,3-dihydrobenzofuran-7-yl)amides, lipophilicity of the acyl moiety was necessary for the potent ACAT inhibitory activity. The highly lipophilic acid amides N-(2,2,4,6-tetramethyl-2,3- dihydrobenzofuran-7-yl)-2,2-dimethyldodecanamide (10) and 6-(4- chlorophenoxy)-N-(2,2,4,6-tetramethyl-2,3-dihydrobenzofuran-7-yl)-2,2- dimethyloctanamide (50) showed potent activity. Introduction of a dimethylamino group at position 5 of the 2,3-dihydrobenzofuran moiety resulted in highly potent activity. The most potent compound, N-[5- (dimethylamino)-2,2,4,6-tetramethyl-2,3-dihydrobenzofuran-7-yl]-2,2- dimethyldodecanamide (13, TEI-6620), showed highly potent ACAT inhibitory activity (rabbit small intestine IC50 = 0.020 μM, rabbit liver IC50 = 0.009 μM), foam cell formation inhibitory activity (rat peritoneal macrophage IC50 = 0.030 μM), extremely potent serum cholesterol-lowering activity in cholesterol-fed rats (71% at a dose of 0.3 mg/kg/day po), and good bioavailability in fed dogs (C(max) = 2.68 μg/mL at 1 h, 10 mg/kg po).