22013-33-8

Basic information

• Product Name: 1,4-Benzodioxan-6-amine
• Synonyms: LABOTEST-BB LT00012696;6-AMINO-1,4-BENZODIOXAN;6-AMINO-1,4-BENZODIOXANE;AKOS AUF02030;AKOS BBS-00000780;3,4-ETHYLENDIOXYANILINE;3,4-ETHYLENEDIOXYANILINE;2,3-DIHYDRO-1,4-BENZODIOXIN-6-AMINE
• CAS NO: 22013-33-8
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16
• EINECS: 244-718-4
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds
• Mol File: 22013-33-8.mol
• Article Data: 14

Chemical Properties

• Melting Point: 29-31 °C(lit.)
• Boiling Point: 116-118°C 3mm
• Flash Point: >230 °F
• Appearance: Brown to black/Viscous Liquid After Melting
• Density: 1.231 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0017mmHg at 25°C
• Refractive Index: n20/D 1.599(lit.)
• Storage Temp.: Store below +30°C.
• PKA: 4.83±0.20(Predicted)
• Water Solubility: insoluble
• Sensitive: Light Sensitive
• BRN: 6447
• CAS DataBase Reference: 1,4-Benzodioxan-6-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Benzodioxan-6-amine(22013-33-8)
• EPA Substance Registry System: 1,4-Benzodioxan-6-amine(22013-33-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-38
• Safety Statements: 26-37/39-36/37-36
• RIDADR: 2810
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 22013-33-8(Hazardous Substances Data)

Usage

Description

1,4-Benzodioxan-6-amine is an organic compound characterized by its brown to black viscous liquid appearance after melting. It is known for its potential applications in various fields, particularly in the pharmaceutical and chemical industries, due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
1,4-Benzodioxan-6-amine is used as a key intermediate in the synthesis of various pharmaceutical compounds with anti-tumor activity. It plays a crucial role in the development of novel anti-cancer drugs, such as N-(2-hydroxy-ethyl)-2,3-didehydroazapodophyllotoxins and dioxanoacridinones, which target and inhibit the growth of cancer cells.
Used in Chemical Research:
1,4-Benzodioxan-6-amine is also utilized as a probe fragment in chemical research, specifically in identifying its ability to induce a conformation in HIV-1 transactivation response element (TAR) RNA. This application is significant in the development of TAR-binding antiviral drugs, which can potentially combat HIV and AIDS.

InChI:InChI=1/C8H9NO2/c9-6-1-2-7-8(5-6)11-4-3-10-7/h1-2,5H,3-4,9H2

Upstream product

• 16498-20-7 6-nitro-2,3-dihydrobenzo[b][1,4]dioxine 
• 493-09-4 benzo-1,4-dioxane 
• 120-80-9 benzene-1,2-diol 
• 52287-51-1 6-bromo-1,4-benzodioxane 
• 62140-78-7 7-nitro-2,3-dihydro-1,4-benzodioxin-6-amine 
• 91861-92-6 N-<3-(2-Hydroxyethoxy)phenyl>hydroxylamine 

Downstream Products

• 173095-01-7 2-(2,3-dihydro-1,4-benzodioxin-6-yl)aminonicotinic acid 
• 438590-29-5 dimethyl 2,3-dihydro[1,4]dioxino[2,3-g]quinoline-7,9-dicarboxylate 
• 90609-94-2 N-(2,3-dihydro-1,4-benzodioxin-6-yl)methylamine 
• 62140-78-7 7-nitro-2,3-dihydro-1,4-benzodioxin-6-amine 
• 154490-83-2 N-(2,3-dihydro-1,4-benzodioxin-6-ylamino)benzoic acid 
• 859825-28-8 7-benzyl-5,6,7,8-tetrahydro-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)pyrido[3,4-d]pyrimidin-4-amine 
• 135574-98-0 N-(2,3-dihydro-1,4-benzodioxin-6-yl)benzylamine 
• 950824-97-2 (2,3-dihydro-benzo[1,4]dioxin-6-yl)-carbamic acid benzyl ester 
• 433963-02-1 8-Methyl-7-phenyl-2,3-dihydro-[1,4]dioxino[2,3-g]quinoline-9-carboxylic acid 
• 1061518-30-6 C₁₆H₁₅FN₂O₂ 
• 1456819-61-6 (7,8-dihydro[1,4]dioxino[2,3-g]quinazolin-4-yl)-(3'-methansulfonamidopheyl)amine hydrochloride 
• 1401243-69-3 (7,8-dihydro[1,4]dioxino[2,3-g]quinazolin-4-yl)-(biphenyl-3'-yl)amine hydrochloride 

Relevant articles and documents

Palladated composite of Cu-BDC MOF and perlite as an efficient catalyst for hydrogenation of nitroarenes

A novel composite of metal-organic framework and perlite is prepared through hydrothermal treatment of terephthalic acid and Cu(NO3)2·3H2O in the presence of perlite. The resulting composite was then utilized as a support for the immobilization of Pd nanoparticles. The obtained compound was characterized via XRD, TGA, ICP, FTIR, TEM, FE-SEM/EDS and elemental mapping analysis and applied as a catalyst for the hydrogenation of nitroarenes under mild reaction condition. The results approved that the catalyst could efficiently promote hydrogenation of various nitroarenes with different electronic densities and steric properties. Moreover, the catalyst showed high selectivity towards hydrogenation of nitro groups. Hot filtration test affirmed heterogeneous nature of catalysis. Furthermore, the present catalytic composite was highly recyclable with low Pd leaching. A comparative study also approved superior activity of the composite compared to palladated perlite and metal-organic framework.

Continuous flow hydrogenation of nitroarenes, azides and alkenes using maghemite-Pd nanocomposites

Maghemite-supported ultra-fine Pd (1-3 nm) nanoparticles, prepared by a simple co-precipitation method, find application in the catalytic continuous flow hydrogenation of nitroarenes, azides, and alkenes wherein they play an important role in the reduction of various functional groups on the surface of maghemite with catalyst loading (~6 wt% Pd). The salient features of the protocol include expeditious formation of reduced products in high yields under near ambient conditions with recycling of the catalyst (up to 12 cycles) without any decrease in selectivity and yield.

Direct metal-free synthesis of diarylamines from 2-nitropropane via the twofold C-H functionalization of arenes

Synthesis of symmetric diarylamines via a twofold intermolecular electrophilic C-H functionalization of electron-rich arenes by umpolung-activated nitroalkane in polyphosphoric acid is demonstrated.