28857-37-6

Basic information

• Product Name: (5-AMINOBENZO[D][1,3]DIOXOL-6-YL)METHANOL
• Synonyms: (5-AMINOBENZO[D][1,3]DIOXOL-6-YL)METHANOL;(6-aminobenzo[d][1,3]dioxol-5-yl)methanol
• CAS NO: 28857-37-6
• Molecular Formula: C₈H₉NO₃
• Molecular Weight: 167.16
• Mol File: 28857-37-6.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (5-AMINOBENZO[D][1,3]DIOXOL-6-YL)METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (5-AMINOBENZO[D][1,3]DIOXOL-6-YL)METHANOL(28857-37-6)
• EPA Substance Registry System: (5-AMINOBENZO[D][1,3]DIOXOL-6-YL)METHANOL(28857-37-6)

Safety Data

• Hazardous Substances Data: 28857-37-6(Hazardous Substances Data)

Usage

General Description

(5-Aminobenzo[d][1,3]dioxol-6-yl)methanol is a chemical compound with a molecular formula C8H9NO3 that consists of a benzene ring fused to a dioxole ring with an attached amino group and a hydroxyl group. It is commonly used in the synthesis of pharmaceuticals, agrochemicals, and dyes. The compound has potential applications in the development of drugs for various therapeutic purposes, including antiviral, anti-inflammatory, and anticancer medications. Additionally, it may be employed as a building block in organic synthesis for the preparation of diverse chemical substances. Due to its unique molecular structure and functional groups, (5-aminobenzo[d][1,3]dioxol-6-yl)methanol offers versatility and potential for various chemical and pharmaceutical 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 articles and documents

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.

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).