69151-39-9

Basic information

• Product Name: benzo[d][1,3]dioxole-4-carboxamide
• Synonyms: benzo[d][1,3]dioxole-4-carboxamide;1,3-Benzodioxole-4-carboxamide
• CAS NO: 69151-39-9
• Molecular Formula: C₈H₇NO₃
• Molecular Weight: 165.14608
• Mol File: 69151-39-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 269.3°C at 760 mmHg
• Flash Point: 141.5°C
• Appearance: /
• Density: 1.384g/cm³
• Vapor Pressure: 0.00731mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: 2-8°C
• CAS DataBase Reference: benzo[d][1,3]dioxole-4-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: benzo[d][1,3]dioxole-4-carboxamide(69151-39-9)
• EPA Substance Registry System: benzo[d][1,3]dioxole-4-carboxamide(69151-39-9)

Safety Data

• Hazardous Substances Data: 69151-39-9(Hazardous Substances Data)

Usage

General Description

Benzo[d][1,3]dioxole-4-carboxamide, also known as carbofuran, is a chemical compound commonly used as a broad-spectrum insecticide. It belongs to the class of carbamate pesticides and is known for its high toxicity to a wide range of insects and other pests. Carbofuran works by inhibiting the activity of the enzyme cholinesterase, which is essential for the normal functioning of the nervous system in insects. This ultimately leads to paralysis and death of the pests. However, carbofuran is also known for its high toxicity to non-target organisms, including birds, mammals, and aquatic life. Due to these environmental and health concerns, its use has been restricted in many countries.

InChI:InChI=1/C8H7NO3/c9-8(10)5-2-1-3-6-7(5)12-4-11-6/h1-3H,4H2,(H2,9,10)

Upstream product

• 5768-39-8 benzo[1,3]dioxole-4-carboxylic acid 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 33842-16-9 benzo[1,3]dioxole-4-carboxylic acid methyl ester 
• 2411-83-8 methyl-2,3-dihydroxybenzoate 
• 1521-38-6 2,3-dimethoxybenzoic acid 
• 303-38-8 2,3-Dihydroxybenzoic acid 
• 24677-78-9 2,3-dihydroxybenzaldehyde 
• 7797-83-3 2H-benzo[d]1,3-dioxolane-4-carbaldehyde 
• 66411-55-0 2,3-(Methylenedioxy)benzoyl chloride 

Downstream Products

• 161886-19-7 benzo[1,3]dioxole-4-carbonitrile 
• 1668-84-4 benzo[d][1,3]dioxol-4-amine 
• 7797-83-3 2H-benzo[d]1,3-dioxolane-4-carbaldehyde 
• 38489-70-2 2,3-(methylenedioxy)cinnamic acid 
• 482-32-6 kokusagine 

Relevant articles and documents

Synthesis of 2,3-dihydrobenzo[b][1,4]dioxine-5-carboxamide and 3-oxo-3,4-dihydrobenzo[b][1,4]oxazine-8-carboxamide derivatives as PARP1 inhibitors

Poly(ADP-ribose) polymerase 1 (PARP1), a widely explored anticancer drug target, plays an important role in single-strand DNA break repair processes. High-throughput virtual screening (HTVS) of a Maybridge small molecule library using the PARP1-benzimidazole-4-carboxamide co-crystal structure and pharmacophore model led to the identification of eleven compounds. These compounds were evaluated using recombinant PARP1 enzyme assay that resulted in the acquisition of three PARP1 inhibitors: 3 (IC50 = 12 μM), 4 (IC50 = 5.8 μM), and 10 (IC50 = 0.88 μM). Compound 4 (2,3-dihydro-1,4-benzodioxine-5-carboxamide) was selected as a lead and was subjected to further chemical modifications, involving analogue synthesis and scaffold hopping. These efforts led to the identification of (Z)-2-(4-hydroxybenzylidene)-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxamide (49, IC50 = 0.082 μM) as the most potent inhibitor of PARP1 from the series.