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193232

Sigma-Aldrich

1,4-Benzodioxan-6-amine

≥98%

Synonym(s):

6-Amino-1,4-benzodioxan

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About This Item

Empirical Formula (Hill Notation):
C8H9NO2
CAS Number:
22013-33-8
Molecular Weight:
151.16
EC Number:
244-718-4
MDL number:
MFCD00006824
UNSPSC Code:
12352100
PubChem Substance ID:
24851588
NACRES:
NA.22

Assay

≥98%

refractive index

n20/D 1.599 (lit.)

mp

29-31 °C (lit.)

density

1.231 g/mL (lit.)

SMILES string

Nc1ccc2OCCOc2c1

InChI

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

InChI key

BZKOZYWGZKRTIB-UHFFFAOYSA-N

Application

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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2, 3-Dihydrodioxin [2, 3-b] acridin-11 (6H)-one.
Karolak-Wojciechowska J, et al.
Acta Crystallographica Section C, Crystal Structure Communications, 54(11), 1689-1690 (1998)
Ajay Kumar et al.
Journal of heterocyclic chemistry, 47(6), 1275-1282 (2011-01-05)
Novel arylamino alcohols were synthesized and these alcohols were used to prepare 12 novel N-(2-hydroxy-ethyl)-2,3-didehydroazapodophyllotoxins, in one step, by simple reflux in ethanol. Isolated yields in the range of 50-70% were obtained.
Elizabeth A Grossman et al.
Cell chemical biology, 24(11), 1368-1376 (2017-09-19)
Many natural products that show therapeutic activities are often difficult to synthesize or isolate and have unknown targets, hindering their development as drugs. Identifying druggable hotspots targeted by covalently acting anti-cancer natural products can enable pharmacological interrogation of these sites

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