1,4-Benzodioxan-6-amine Chemical Properties

Melting point:

29-31 °C (lit.)

Boiling point:

116-118°C 3mm

Density 

1.231 g/mL (lit.)

refractive index 

n20/D 1.599(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

form 

Viscous Liquid After Melting

pka

4.83±0.20(Predicted)

Specific Gravity

1.231

color 

Brown to black

Water Solubility 

insoluble

Sensitive 

Light Sensitive

BRN 

6447

InChI

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

InChIKey

BZKOZYWGZKRTIB-UHFFFAOYSA-N

SMILES

O1C2=CC=C(N)C=C2OCC1

CAS DataBase Reference

22013-33-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38-38

Safety Statements 

26-37/39-36/37-36

RIDADR 

2810

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

6.1

PackingGroup 

III

HS Code 

29329995

MSDS

• Language:English Provider:1,4-Benzodioxan-6-amine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
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1,4-Benzodioxan-6-amine Usage And Synthesis

Chemical Properties

brown to black viscous liquid after melting

Uses

1,4-Benzodioxan-6-amine was used in the synthesis of N-(2-hydroxy-ethyl)-2,3-didehydroazapodophyllotoxins having anti-tumor activity and dioxanoacridinones.

Uses

3,4-Ethylenedioxyaniline is a probe fragment screened to identify its ability to induce a conformation in HIV-1 transactivation response element (TAR) RNA in efforts to develop TAR-binding antiviral d rugs.

Synthesis

(3) In a 2L autoclave, 102.0 g (0.54 mol) of 6-nitro-2,3-dihydrobenzo[b][1,4]dioxane (Intermediate 2) and 3.7 g of palladium/carbon catalyst were added, 700 g of tetrahydrofuran (THF), and the reaction was carried out at a temperature of 40~45°C and a pressure of 5~7 atm of hydrogen for 10 h. Upon completion of the reaction, the palladium/carbon catalyst was filtered and recovered. After the reaction, the filtrate was distilled under reduced pressure to remove THF to give 62.2 g of reddish brown oily liquid (Intermediate 3) in 76.3% yield.

References

[1] Catalysis Science and Technology, 2016, vol. 6, # 1, p. 152 - 160
[2] Chemical Communications, 2012, vol. 48, # 64, p. 7982 - 7984
[3] Dalton Transactions, 2016, vol. 45, # 17, p. 7421 - 7426
[4] Patent: CN105859678, 2016, A. Location in patent: Paragraph 0078; 0079
[5] Russian Chemical Bulletin, 2009, vol. 58, # 6, p. 1233 - 1240

1,4-Benzodioxan-6-amine(22013-33-8)Related Product Information

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• 2,3-DIHYDRO-1,4-BENZODIOXIN-6-YL ISOTHIOCYANATE