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538523

Sigma-Aldrich

6-Bromo-1,4-benzodioxane

97%

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Empirical Formula (Hill Notation):
C8H7BrO2
CAS Number:
Molecular Weight:
215.04
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

refractive index

n20/D 1.588 (lit.)

bp

259-260 °C (lit.)

density

1.598 g/mL at 25 °C (lit.)

SMILES string

Brc1ccc2OCCOc2c1

InChI

1S/C8H7BrO2/c9-6-1-2-7-8(5-6)11-4-3-10-7/h1-2,5H,3-4H2

InChI key

LFCURAJBHDNUNG-UHFFFAOYSA-N

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This Item
563013343870640441
vibrant-m

538523

6-Bromo-1,4-benzodioxane

vibrant-m

640441

4-Bromo-1,2-diaminobenzene

assay

97%

assay

97%

assay

99%

assay

97%

density

1.598 g/mL at 25 °C (lit.)

density

-

density

1.62 g/mL at 25 °C (lit.)

density

-

bp

259-260 °C (lit.)

bp

-

bp

-

bp

-

refractive index

n20/D 1.588 (lit.)

refractive index

-

refractive index

n20/D 1.462 (lit.)

refractive index

-

General description

6-Bromo-1,4-benzodioxane is an aryl halide. It can be synthesized from 1,4-benzodioxane, via bromination with bromine in acetic acid. It undergoes alkoxycarbonylation reaction with sodium tert-butoxide in the presence of CO to yield 2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid t-butyl ester.

Application

6-Bromo-1,4-benzodioxane may be used as a starting reagent in the synthesis of chiral diphosphines (SYNPHOS and DIFLUORPHOS).

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)


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Chiral biphenyl diphosphines for asymmetric catalysis: Stereoelectronic design and industrial perspectives.
Jeulin, Severine, et al.
Proceedings of the National Academy of Sciences of the USA, 101(16), 5799-5804 (2004)
An Efficient Method for the Preparation of Tertiary Esters by Palladium-Catalyzed Alkoxycarbonylation of Aryl Bromides.
Xin, Zhuo, et al.
Organic Letters, 14(1), 284-287 (2011)

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