2,6-dibromophenol

Structural formula
General
Surname	2,6-dibromophenol
Molecular formula	C 6 H 4 Br 2 O
Brief description	whitish crystalline powder with a phenolic odor
External identifiers / databases
EC number	210-161-0
ECHA InfoCard	100.009.238
PubChem	11847
Wikidata	Q209273
properties
Molar mass	251.9 g mol −1
Physical state	firmly
Melting point	56-57 ° C
boiling point	162 ° C (28 h Pa ); 255-256 ° C;
pK s value	6.67 (25 ° C)
solubility	slightly soluble in water
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-312-332
	P: 280
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2,6-Dibromophenol is a chemical compound that belongs to both the phenols and the halogen aromatic compounds .

Occurrence in nature

2,6-Dibromophenol was found in the sea worms Balanoglossus biminiensis .

Derivatives

The methyl ether can be prepared by methylation with dimethyl sulfate and is also known under the common name 2,6-dibromanisole . Its melting point is 13 ° C, its boiling point at 34 mmHg at 143-145 ° C.

The ethyl ether ( 2,6-dibromophenetol ) melts at 40.5 ° C.

Esterification with acetic anhydride yields the acetate, which melts at 46 ° C (CAS number: 28165-72-2).

Further bromination of 2,6-dibromophenol with bromine in potassium bromide solution gives 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 .

The nitration of 2,6-dibromophenol with nitric acid yields 2,6-dibromo-4-nitrophenol (CAS number: 99-28-5, melting point 144–145 ° C).

Individual evidence

↑ ^a ^b ^c data sheet 2,6-dibromophenol from AlfaAesar, accessed on August 2, 2010 ( PDF )(JavaScript required) .
↑ ^a ^b ^c ^d ^e ^f ^g Dictionary of organic compounds, p. 1971 ( limited preview in the Google book search).
↑ ^a ^b data sheet 2,6-dibromophenol from Sigma-Aldrich , accessed on March 19, 2011 ( 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).
^ FG Pope, AS Wood: "CXCIII.-The bromination of phenol. 2: 4- and 2: 6-dibromophenol" in J. Chem. Soc., Trans. 1912 , 101 , pp. 1823-1829. doi : 10.1039 / CT9120101823
^ WW Hartman, JB Dickey: 2,6-Dibromo-4-nitrophenol In: Organic Syntheses . 15, 1935, p. 6, doi : 10.15227 / orgsyn.015.0006 ; Coll. Vol. 2, 1943, p. 173 ( PDF ).

[Alfa-1] ta sheet 2,6-dibromophenol from AlfaAesar, accessed on August 2, 2010 ( PDF )(JavaScript required) .

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

[Sigma-3] ta sheet 2,6-dibromophenol from Sigma-Aldrich , accessed on March 19, 2011 ( PDF ).

[Price-4] John A. Price: "The Structure of Tribromophenol bromide", in: J. Am. Chem. Soc. , 1955 , 77 (20), pp. 5436-5437; doi : 10.1021 / ja01625a081 .

[Latscha-5] Hans P. Latscha, Helmut A. Klein, Gerald W. Linti: "Analytical Chemistry: Chemistry-Basiswissen III", p. 287 ( limited preview in the Google book search).

[Pope-6] FG Pope, AS Wood: "CXCIII.-The bromination of phenol. 2: 4- and 2: 6-dibromophenol" in J. Chem. Soc., Trans. 1912 , 101 , pp. 1823-1829. doi : 10.1039 / CT9120101823

[Hartman-7] WW Hartman, JB Dickey: 2,6-Dibromo-4-nitrophenol In: Organic Syntheses . 15, 1935, p. 6, doi : 10.15227 / orgsyn.015.0006 ; Coll. Vol. 2, 1943, p. 173 ( PDF ).