28857-37-6

Usage

Uses

Used in Pharmaceutical Industry:
(5-Aminobenzo[d][1,3]dioxol-6-yl)methanol is used as an intermediate in the synthesis of various drugs for therapeutic purposes, including antiviral, anti-inflammatory, and anticancer medications. Its unique molecular structure and functional groups contribute to its potential in developing novel pharmaceutical compounds.
Used in Agrochemical Industry:
In the agrochemical industry, (5-Aminobenzo[d][1,3]dioxol-6-yl)methanol serves as a key component in the development of new agrochemical products, such as pesticides and herbicides, due to its chemical properties and reactivity.
Used in Dye Industry:
(5-Aminobenzo[d][1,3]dioxol-6-yl)methanol is used as a building block in the synthesis of dyes, taking advantage of its chemical structure to create a wide range of colorants for various applications.
Used in Organic Synthesis:
As a versatile compound, (5-Aminobenzo[d][1,3]dioxol-6-yl)methanol is employed as a starting material in organic synthesis for the preparation of diverse chemical substances, showcasing its potential in various chemical applications.

Upstream product

• 712-97-0 6-nitro-1,3-benzodioxole-5-carbaldehyde 
• 20332-16-5 4,5-methylenedioxyanthranilic acid 
• 15341-08-9 (6-nitrobenzo[d][1,3]dioxol-5-yl)methanol 

Downstream Products

• 1027580-09-1 C₁₈H₁₇NSO₈H₂ 
• 942614-47-3 2-(4-(N-(6-(1H-benzimidazol-2-yl)benzo[1,3]-dioxol-5-yl)sulfamoyl)phenoxy)acetic acid ethyl ester 
• 942614-42-8 2-(4-(N-(6-formylbenzo[1,3]-dioxol-5-yl)sulfamoyl)phenoxy)acetic acid ethyl ester 

Relevant academic research and scientific papers

Metal- and Protection-Free [4 + 2] Cycloadditions of Alkynes with Azadienes: Assembly of Functionalized Quinolines

A base promoted, protection-free, and regioselective synthesis of highly functionalized quinolines via [4 + 2] cycloaddition of azadienes (generated in situ from o-aminobenzyl alcohol) with internal alkynes has been discovered. The reaction tolerates a wide variety of functional groups which has been successfully extended with diynes, (2-aminopyridin-3-yl)methanol, and 1,4-bis(phenylethynyl)benzene to afford (Z)-phenyl-2-styrylquinolines, phenylnaphthyridine, and alkyne-substituted quinolines, respectively. The proposed mechanism and significant role of the solvent were well supported by isolating the azadiene intermediate and deuterium-labeling studies.

Regioselective Synthesis of C-3-Functionalized Quinolines via Hetero-Diels-Alder Cycloaddition of Azadienes with Terminal Alkynes

A highly efficient metal and protection-free approach for the regioselective synthesis of C-3-functionalized quinolines from azadienes (in situ generated from 2-aminobenzyl alcohol) and terminal alkynes through [4 + 2] cycloaddition has been developed. An unprecedented reaction of 2-aminobenzyl alcohol with 1,3- and 1,4-diethynylbenzene provided the C-3 tolylquinolines via [4 + 2] HDA and oxidative decarboxylation. The -NH2 group directed mechanistic approach was well supported by the control experiments and deuterium-labeling studies and by isolating the azadiene intermediate. The reactivity and selectivity of unprotected azadiene in metal-free base-assisted hetero-Diels-Alder reaction is exploited to quickly assemble an important class of C-3-functionalized quinolines, which are difficult to access.

One-pot catalytic enantioselective synthesis of functionalized tetrahydroquinolines by aza-michael/michael cascade reactions of N-protected 2-aminophenyl α,β-unsaturated esters with Nitroolefins

A highly enantioselective synthesis of functionalized tetrahydroquinolines with useful biological properties has been developed by means of asymmetric organocatalytic aza-Michael/Michael cascade reactions of nitroolefins with N-protected 2-aminophenyl α,β-unsaturated esters in the presence of a chiral thiourea catalyst. The reaction gave the corresponding highly functionalized tetrahydroquinolines in good yields, excellent diastereoselectivities (>30:1 dr), and high enantioselectivities (≤99% ee).

Excited-state intramolecular proton transfer in 2-(2′- arylsulfonamidophenyl)benzimidazole derivatives: The effect of donor and acceptor substituents

(Chemical Equation Presented) A series of water-soluble 2-(2′-arylsulfonamidophenyl)benzimidazole derivatives containing electron-donating and accepting groups attached to various positions of the fluorophore π-system has been synthesized and characterize