2,4-dibromophenol

Structural formula
General
Surname	2,4-dibromophenol
other names	2,4-dibromo-1-hydroxybenzene
Molecular formula	C 6 H 4 Br 2 O
Brief description	white to light brown solid with a phenolic odor
External identifiers / databases
EC number	210-436-5
ECHA InfoCard	100.009.488
PubChem	12005
Wikidata	Q209199
properties
Molar mass	251.9 g mol −1
Physical state	firmly
Melting point	40 ° C
boiling point	239 ° C; 154 ° C (15 h Pa );
Vapor pressure	386 mPa (25 ° C)
pK s value	7.79 (25 ° C)
solubility	2.2 g l −1
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 300-315-319-335
	P: 261-264-301 + 310-305 + 351 + 338
Toxicological data	> 2000 mg kg −1 ( LD 50 , rabbit , transdermal )
	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).

[Alfa-1] ta sheet 2,4-dibromophenol from AlfaAesar, accessed on August 2, 2010 ( PDF )(JavaScript required) .

[DOC-2] ↑ ^a ^b ^c ^d ^e ^f Dictionary of organic compounds, p. 1971 ( limited preview in Google book search).

[Sigma-3] ta sheet 2,4-dibromophenol from Sigma-Aldrich , accessed on April 26, 2011 ( PDF ).

[Howe-4] Paul Howe et al .: "2,4,6-tribromophenol and other simple brominated Phenols" ( limited preview in the Google book search).

[Hashimoto-5] 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 .

[Price-6] John A. Price: "The Structure of Tribromophenol bromide", in: J. Am. Chem. Soc. , 1955 , 77 (20), pp. 5436-5437; doi : 10.1021 / ja01625a081 .

[Latscha-7] Hans P. Latscha, Helmut A. Klein, Gerald W. Linti: "Analytical Chemistry: Chemistry-Basiswissen III", p. 287 ( limited preview in the Google book search).