2,4-dibromophenol
Structural formula | ||||||||||||||||
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General | ||||||||||||||||
Surname | 2,4-dibromophenol | |||||||||||||||
other names |
2,4-dibromo-1-hydroxybenzene |
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Molecular formula | C 6 H 4 Br 2 O | |||||||||||||||
Brief description |
white to light brown solid with a phenolic odor |
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External identifiers / databases | ||||||||||||||||
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properties | ||||||||||||||||
Molar mass | 251.9 g mol −1 | |||||||||||||||
Physical state |
firmly |
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Melting point |
40 ° C |
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boiling point |
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Vapor pressure |
386 mPa (25 ° C) |
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pK s value |
7.79 (25 ° C) |
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solubility |
2.2 g l −1 |
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safety instructions | ||||||||||||||||
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Toxicological data |
> 2000 mg kg −1 ( LD 50 , rabbit , transdermal ) |
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
2,4-Dibromophenol is a chemical compound that belongs to both the phenols and the halogen aromatic compounds .
presentation
2,4-Dibromophenol can be produced by bromination of 3-trimethylsilylphenol with stoichiometric amounts of elemental bromine and subsequent hydrolysis . When using excess bromine, 2,3,4,6-tetrabromophenol is formed .
properties
The flash point of 2,4-dibromophenol is 113 ° C.
Derivatives
The methyl ether can be produced by methylation with dimethyl sulfate and is also known under the common name 2,4-dibromanisole . Its melting point is 61.5 ° C and its boiling point is 272 ° C.
The ethyl ether with the common name 2,4-dibromophenetol (CAS number: 38751-57-4) melts at 53.5 ° C.
Esterification with acetic anhydride yields the acetate, which melts at 36 ° C (CAS number: 36914-79-1).
Further bromination of 2,4-dibromophenol with bromine in potassium bromide solution yields 2,4,6-tribromophenol , which in turn reacts further with bromine to form 2,4,4,6-tetrabromo-2,5-cyclohexadienone . This reaction can be reversed by hydrogen iodide .
Individual evidence
- ↑ a b c data sheet 2,4-dibromophenol from AlfaAesar, accessed on August 2, 2010 ( PDF )(JavaScript required) .
- ↑ a b c d e f Dictionary of organic compounds, p. 1971 ( limited preview in Google book search).
- ↑ a b c d data sheet 2,4-dibromophenol from Sigma-Aldrich , accessed on April 26, 2011 ( PDF ).
- ↑ a b Paul Howe et al .: "2,4,6-tribromophenol and other simple brominated Phenols" ( limited preview in the Google book search).
- ↑ Tadashi Hashimoto: "Synthesis of Organosilicon Compounds VII. On the Reaction of 3-Trimethylsilylphenol with Electrophilic Reagents", in: Yakugaku Zasshi , 1960 , 80 , pp. 1399-1404; PDF .
- ↑ John A. Price: "The Structure of Tribromophenol bromide", in: J. Am. Chem. Soc. , 1955 , 77 (20), pp. 5436-5437; doi : 10.1021 / ja01625a081 .
- ↑ Hans P. Latscha, Helmut A. Klein, Gerald W. Linti: "Analytical Chemistry: Chemistry-Basiswissen III", p. 287 ( limited preview in the Google book search).