Bromodihydroxybenzenes

The bromodihydroxybenzenes form a group of aromatic compounds which are derived from phenol or dihydroxybenzenes as well as from bromobenzene . The structure consists of a benzene ring with two attached hydroxyl groups  (-OH) and a bromine atom  (-Br) as substituents . Their different arrangement results in six constitutional isomers with the empirical formula C ₆ H ₅ BrO ₂ .

Uniform naming is difficult because the dihydroxybenzenes do not form a common common name. They can therefore be understood as derivatives of catechol (2 isomers), resorcinol (3 isomers) and hydroquinone (1 isomer). Conversely, they can be viewed as dihydroxy derivatives of bromobenzene. Since the phenolic component predominates here, bromodihydroxybenzenes , i.e. derivatives of dihydroxybenzenes, are more obvious here.

Bromodihydroxybenzenes
Surname	3-bromopyrocatechol , 1,2-dihydroxy- 3-bromobenzene	4-bromopyrocatechol , 1,2-dihydroxy- 4-bromobenzene	2-bromoresorcinol , 1,3-dihydroxy- 2-bromobenzene	4-bromoresorcinol , 1,3-dihydroxy- 4-bromobenzene	5-bromoresorcinol , 1,3-dihydroxy- 5-bromobenzene	Bromohydroquinone , 1,4-dihydroxy- 2-bromobenzene
Structural formula
CAS number	14381-51-2	17345-77-6	6751-15-9	6626-15-9	106120-04-1	583-69-7
PubChem	26659	28487	604810	81105	557383	68502
Molecular formula	C 6 H 5 BrO 2
Molar mass	189.01 g mol −1
Physical state	firmly
Melting point	39-42 ° C	87 ° C	102-103 ° C	99-102 ° C		112-116 ° C
boiling point	118–120 ° C (12 hPa )			150 ° C (16 hPa)
pK s value	9.40	pK s 1  = 8.7 pK s 2  = 12.4				pK s 1  = 8.67 pK s 2  = 10.68
GHS labeling	Caution	no classification available	no classification available	Caution	no classification available	Caution
H and P phrases	315-319-335	see above	see above	302-312-315-319-332-335	see above	315-319-335
	no EUH phrases	see above	see above	no EUH phrases	see above	no EUH phrases
	261-302 + 352 305 + 351 + 338-321-405-501	see above	see above	261-280-305 + 351 + 338	see above	261-305 + 351 + 338

Individual evidence

1. ↑ ^{a b} Data sheet 3-Bromocatechol from AlfaAesar, accessed on August 15, 2010 ( PDF )(JavaScript required) .
2. ↑ ^{a b c d e f g} Dictionary of organic compounds , p. 932 ( limited preview in Google book search).
3. ↑ ^{a b} Data sheet 4-Bromoresorcinol, 98% from Acros, accessed on February 22, 2010.
4. ^ Entry on Bromhydroquinone at ChemicalBook , accessed on September 19, 2011.
5. ^ Howard S. Mason: "The allergenic Principles of Poison Ivy. VI. Note on the Synthesis of 3-Substituted Catechols ”, in: J. Am. Chem. Soc. , 1947 , 69  (9), pp. 2241-2242; doi : 10.1021 / ja01201a514 .
6. ↑ Data sheet 4-bromoresorcinol from Sigma-Aldrich , accessed on March 18, 2011 ( PDF ).
7. ↑ Datasheet Bromohydroquinone from Sigma-Aldrich , accessed on March 14, 2011 ( PDF ).

Web links

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