2,4,6-tribromanisole

Structural formula
General
Surname	2,4,6-tribromanisole
other names	2,4,6-tribromo-1-methoxybenzene
Molecular formula	C 7 H 5 Br 3 O
Brief description	colorless solid
External identifiers / databases
EC number	627-908-5
ECHA InfoCard	100.156.226
PubChem	11839
ChemSpider	21170966
Wikidata	Q4596770
properties
Molar mass	344.83 g mol −1
Physical state	firmly
density	2.49 g cm −3
Melting point	84-88 ° C
boiling point	297-299 ° C
solubility	practically insoluble in water (1.85 mg l −1 at 25 ° C); slightly soluble in ethanol ; very soluble in acetone and benzene ; soluble in carbon tetrachloride ;
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: 413
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2,4,6-tribromanisole is an aromatic compound . The structure consists of a benzene ring with an attached methoxy group (–OCH ₃ ) and three bromine atoms (–Br) as substituents .

Occurrence

2,4,6-tribromanisole was identified in 2004 by Pascal Chatonnet as a musty odor component of some wines . The connection has also been detected in fish and marine sediments.

Extraction and presentation

2,4,6-Tribromanisole can be obtained by O -methylation of its direct precursor 2,4,6-tribromophenol . Since it also occurs as a metabolite of the compound used as a fungicide , it is held responsible for odor defects in food.

properties

2,4,6-Tribromanisole is a colorless solid with a musty odor that is practically insoluble in water. It can be perceived even in very low concentrations.

use

2,4,6-Tribromanisole is used in the manufacture of dyes, flame retardants and brominated aromatic compounds.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 2,4,6-tribromanisole in the Hazardous Substances Data Bank , accessed on July 16, 2017.
↑ ^a ^b ^c ^d ^e data sheet 2,4,6-tribromoanisole, 99% from Sigma-Aldrich , accessed on July 16, 2017 ( PDF ).
↑ Practical Winery & Vineyard Journal: Wine Microbiology: 2,4,6-TBA | Practical Winery & Vineyard Journal , accessed July 16, 2017.
↑ Pascal Chatonnet, Sandra Bonnet, Stéphane Boutou, Marie-Dominique Labadie: Identification and Responsibility of 2,4,6-Tribromoanisole in Musty, Corked Odors in Wine. In: Journal of Agricultural and Food Chemistry , 52, 2004, pp. 1255-1262, doi : 10.1021 / jf030632f .
↑ George Ware: Reviews of Environmental Contamination and Toxicology 188 . Springer Science & Business Media, 2007, ISBN 978-0-387-32964-2 , pp. 34 ( limited preview in Google Book search).
^ Andrew G. Reynolds: Managing Wine Quality Oenology and Wine Quality . Elsevier, 2010, ISBN 978-1-84569-998-7 , pp. 415 ( limited preview in Google Book search).
^ Frank B. Whitfield, Jodie L. Hill, Kevin J. Shaw: 2,4,6-Tribromoanisole: a Potential Cause of Mustiness in Packaged Food. In: Journal of Agricultural and Food Chemistry , 45, 1997, pp. 889-993, doi : 10.1021 / jf960587u .
↑ Leif H. Skibsted, Jens Risbo, Mogens L. Andersen: Chemical Deterioration and Physical Instability of Food and Beverages . Elsevier, 2010, ISBN 978-1-84569-926-0 , pp. 352 ( limited preview in Google Book search).

Web links

Commons : 2,4,6-Tribromanisole - Collection of pictures, videos and audio files

Entry to 2,4,6-tribromanisole . In: P. J. Linstrom, W. G. Mallard (Eds.): NIST Chemistry WebBook, NIST Standard Reference Database Number 69 . National Institute of Standards and Technology , Gaithersburg MD
Wine lexicon: cork taste

[HSDB-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 2,4,6-tribromanisole in the Hazardous Substances Data Bank , accessed on July 16, 2017.

[Sigma-2] ↑ ^a ^b ^c ^d ^e data sheet 2,4,6-tribromoanisole, 99% from Sigma-Aldrich , accessed on July 16, 2017 ( PDF ).

[Practical_Winery_&_Vineyard_Journal-3] Practical Winery & Vineyard Journal: Wine Microbiology: 2,4,6-TBA | Practical Winery & Vineyard Journal , accessed July 16, 2017.

[DOI10.1021/jf030632f-4] Pascal Chatonnet, Sandra Bonnet, Stéphane Boutou, Marie-Dominique Labadie: Identification and Responsibility of 2,4,6-Tribromoanisole in Musty, Corked Odors in Wine. In: Journal of Agricultural and Food Chemistry , 52, 2004, pp. 1255-1262, doi : 10.1021 / jf030632f .

[George_Ware-5] George Ware: Reviews of Environmental Contamination and Toxicology 188 . Springer Science & Business Media, 2007, ISBN 978-0-387-32964-2 , pp. 34 ( limited preview in Google Book search).

[Andrew_G._Reynolds-6] Andrew G. Reynolds: Managing Wine Quality Oenology and Wine Quality . Elsevier, 2010, ISBN 978-1-84569-998-7 , pp. 415 ( limited preview in Google Book search).

[DOI10.1021/jf960587u-7] Frank B. Whitfield, Jodie L. Hill, Kevin J. Shaw: 2,4,6-Tribromoanisole: a Potential Cause of Mustiness in Packaged Food. In: Journal of Agricultural and Food Chemistry , 45, 1997, pp. 889-993, doi : 10.1021 / jf960587u .

[Leif_H._Skibsted,_Jens_Risbo,_Mogens_L._Andersen-8] Leif H. Skibsted, Jens Risbo, Mogens L. Andersen: Chemical Deterioration and Physical Instability of Food and Beverages . Elsevier, 2010, ISBN 978-1-84569-926-0 , pp. 352 ( limited preview in Google Book search).