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302384

Sigma-Aldrich

2,4,4,6-Tetrabromo-2,5-cyclohexadienone

90%

Synonym(s):

TBCO

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About This Item

Empirical Formula (Hill Notation):
C6H2Br4O
CAS Number:
Molecular Weight:
409.70
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

assay

90%

form

solid

storage temp.

2-8°C

SMILES string

BrC1=CC(Br)(Br)C=C(Br)C1=O

InChI

1S/C6H2Br4O/c7-3-1-6(9,10)2-4(8)5(3)11/h1-2H

InChI key

NJQJGRGGIUNVAB-UHFFFAOYSA-N

General description

2,4,4,6-Tetrabromo-2,5-cyclohexadienone forms solid charge-transfer molecular complexes with 4-(aminomethyl)piperidine and their spectroscopic characteristics were studied.

Application

2,4,4,6-Tetrabromo-2,5-cyclohexadienone was used as catalyst for efficient deoxygenation of sulfoxides to their corresponding sulfides with 1,3-dithiane. It was also used as reagent for conversion of alcohols to azides.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

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Adel Mostafa et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 118, 1012-1019 (2013-11-05)
The spectroscopic characteristics of the solid charge-transfer molecular complexes (CT) formed in the reaction of the electron donor 4-(aminomethyl) piperidine (4AMP) with the σ-acceptor iodine and the π-acceptors 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), 2,4,4,6-tetrabromo-2,5-cyclohexadienone (TBCHD) and 7,7,8,8-tetracyanoquinodimethane (TCNQ) have been studied in chloroform
Giulia Simonetti et al.
International journal of environmental research and public health, 17(11) (2020-05-31)
The occurrence of halogenated organic pollutants in indoor dust can be high due to the presence of textile, electronic devices, furniture, and building materials treated with these chemicals. In this explorative study, we focused on emerging organic pollutants, such as
An efficient method for converting alcohols to azides with 2, 4, 4, 6-tetrabromo-2, 5-cyclohexadienone/PPh3 /Zn (N3)2? 2Py.
Saito A, et al.
Tetrahedron Letters, 38(22), 3955-3958 (1997)
Jakob Gustavsson et al.
Journal of chromatography. A, 1524, 74-86 (2017-10-17)
The influence of natural organic matter (NOM) on the solid-phase extraction (SPE) efficiency was investigated for legacy and emerging flame retardants (FRs; n=26) in surface water. Three different groups of FRs were analyzed: polybrominated diphenyl ethers (PBDEs), halogenated flame retardants
Darren Van Essen et al.
Chemosphere, 266, 129195-129195 (2020-12-15)
Brominated flame retardants (BFRs) can enter aquatic environments where they can have adverse effects on organisms. The BFR, 1,2,5,6-Tetrabromocyclooctane (TBCO), has been introduced as a potential replacement for the major use BRF, Hexabromocyclododecane (HBCD). However, little is known about effects

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