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bromophenol blue
3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 3,5-dibromo-4-hydroxyphenyl groups. It is used as a laboratory indicator, changing from yellow below pH 3 to purple at pH 4.6, and as a size marker for monitoring the progress of agarose gel and polyacrylamide gel electrophoresis. It has also been used as an industrial dye.

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05. Industrial Uses

			indicator [CHEBI:47867] (23)

					visual indicator [CHEBI:50408] (4)

						colour indicator [CHEBI:50410] (4)

							acid-base indicator [CHEBI:50407] (3)

bromophenol blue [CHEBI:59424] (1)

							two-colour indicator [CHEBI:50412] (3)

bromophenol blue [CHEBI:59424] (1)

			dye [CHEBI:37958] (446)

bromophenol blue [CHEBI:59424] (1)

08. Chemical Category

			main group molecular entity [CHEBI:33579] (25650)

					s-block molecular entity [CHEBI:33674] (7287)

							hydrogen molecular entity [CHEBI:33608] (6932)

								hydroxides [CHEBI:24651] (5641)

									organic hydroxy compound [CHEBI:33822] (3050)

phenols [CHEBI:33853] (868)

bromophenol blue [CHEBI:59424] (1)

					p-block molecular entity [CHEBI:33675] (25343)

						halogen molecular entity [CHEBI:24471] (1475)

								bromine molecular entity [CHEBI:22928] (199)

organobromine compound [CHEBI:37141] (138)

bromophenol blue [CHEBI:59424] (1)

								halide [CHEBI:37578] (1402)

									organohalogen compound [CHEBI:36684] (976)

organobromine compound [CHEBI:37141] (138)

bromophenol blue [CHEBI:59424] (1)

						chalcogen molecular entity [CHEBI:33304] (15225)

								oxygen molecular entity [CHEBI:25806] (14414)

hydroxides [CHEBI:24651] (5641)

organic hydroxy compound [CHEBI:33822] (3050)

phenols [CHEBI:33853] (868)

bromophenol blue [CHEBI:59424] (1)

organooxygen compound [CHEBI:36963] (11352)

oxacycle [CHEBI:38104] (2002)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

								sulfur molecular entity [CHEBI:26835] (1541)

organosulfur compound [CHEBI:33261] (1005)

organosulfur heterocyclic compound [CHEBI:38106] (367)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

sulfur oxoacid derivative [CHEBI:33424] (628)

sulfonic acid derivative [CHEBI:33552] (393)

arenesulfonate ester [CHEBI:38094] (12)

bromophenol blue [CHEBI:59424] (1)

								organochalcogen compound [CHEBI:36962] (11874)

									organosulfur compound [CHEBI:33261] (1005)

organosulfur heterocyclic compound [CHEBI:38106] (367)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

									organooxygen compound [CHEBI:36963] (11352)

oxacycle [CHEBI:38104] (2002)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

						carbon group molecular entity [CHEBI:33582] (23847)

							organic molecular entity [CHEBI:50860] (23769)

								heteroorganic entity [CHEBI:33285] (15197)

organic heterocyclic compound [CHEBI:24532] (5243)

oxacycle [CHEBI:38104] (2002)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

organosulfur heterocyclic compound [CHEBI:38106] (367)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

organic heteropolycyclic compound [CHEBI:38166] (2613)

organic heterobicyclic compound [CHEBI:27171] (1315)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

organohalogen compound [CHEBI:36684] (976)

organobromine compound [CHEBI:37141] (138)

bromophenol blue [CHEBI:59424] (1)

organochalcogen compound [CHEBI:36962] (11874)

organosulfur compound [CHEBI:33261] (1005)

organosulfur heterocyclic compound [CHEBI:38106] (367)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

organooxygen compound [CHEBI:36963] (11352)

oxacycle [CHEBI:38104] (2002)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

								organic hydroxy compound [CHEBI:33822] (3050)

phenols [CHEBI:33853] (868)

bromophenol blue [CHEBI:59424] (1)

								ester [CHEBI:35701] (3370)

sultone [CHEBI:38088] (2)

bromophenol blue [CHEBI:59424] (1)

								organic molecule [CHEBI:72695] (11399)

									organic cyclic compound [CHEBI:33832] (7633)

organic heterocyclic compound [CHEBI:24532] (5243)

oxacycle [CHEBI:38104] (2002)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

organosulfur heterocyclic compound [CHEBI:38106] (367)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

organic heteropolycyclic compound [CHEBI:38166] (2613)

organic heterobicyclic compound [CHEBI:27171] (1315)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

organic aromatic compound [CHEBI:33659] (3593)

phenols [CHEBI:33853] (868)

bromophenol blue [CHEBI:59424] (1)

			polyatomic entity [CHEBI:36357] (18777)

				molecule [CHEBI:25367] (11520)

						cyclic compound [CHEBI:33595] (7817)

								polycyclic compound [CHEBI:33635] (4078)

heteropolycyclic compound [CHEBI:33671] (2613)

organic heteropolycyclic compound [CHEBI:38166] (2613)

organic heterobicyclic compound [CHEBI:27171] (1315)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

								bicyclic compound [CHEBI:33636] (1511)

heterobicyclic compound [CHEBI:33672] (1315)

organic heterobicyclic compound [CHEBI:27171] (1315)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

								aromatic compound [CHEBI:33655] (3799)

organic aromatic compound [CHEBI:33659] (3593)

phenols [CHEBI:33853] (868)

bromophenol blue [CHEBI:59424] (1)

								organic cyclic compound [CHEBI:33832] (7633)

organic heterocyclic compound [CHEBI:24532] (5243)

oxacycle [CHEBI:38104] (2002)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

organosulfur heterocyclic compound [CHEBI:38106] (367)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

organic heteropolycyclic compound [CHEBI:38166] (2613)

organic heterobicyclic compound [CHEBI:27171] (1315)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

organic aromatic compound [CHEBI:33659] (3593)

phenols [CHEBI:33853] (868)

bromophenol blue [CHEBI:59424] (1)

								heterocyclic compound [CHEBI:5686] (5275)

									organic heterocyclic compound [CHEBI:24532] (5243)

oxacycle [CHEBI:38104] (2002)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

organosulfur heterocyclic compound [CHEBI:38106] (367)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

organic heteropolycyclic compound [CHEBI:38166] (2613)

organic heterobicyclic compound [CHEBI:27171] (1315)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

									heteropolycyclic compound [CHEBI:33671] (2613)

organic heteropolycyclic compound [CHEBI:38166] (2613)

organic heterobicyclic compound [CHEBI:27171] (1315)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

									heterobicyclic compound [CHEBI:33672] (1315)

organic heterobicyclic compound [CHEBI:27171] (1315)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

						organic molecule [CHEBI:72695] (11399)

							organic cyclic compound [CHEBI:33832] (7633)

								organic heterocyclic compound [CHEBI:24532] (5243)

oxacycle [CHEBI:38104] (2002)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

organosulfur heterocyclic compound [CHEBI:38106] (367)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

organic heteropolycyclic compound [CHEBI:38166] (2613)

organic heterobicyclic compound [CHEBI:27171] (1315)

benzoxathiole [CHEBI:38086] (3)

2,1-benzoxathiole [CHEBI:38087] (2)

bromophenol blue [CHEBI:59424] (1)

								organic aromatic compound [CHEBI:33659] (3593)

									phenols [CHEBI:33853] (868)

bromophenol blue [CHEBI:59424] (1)

				heteroatomic molecular entity [CHEBI:37577] (13672)

					hydroxides [CHEBI:24651] (5641)

							organic hydroxy compound [CHEBI:33822] (3050)

								phenols [CHEBI:33853] (868)

bromophenol blue [CHEBI:59424] (1)

					oxoacid derivative [CHEBI:33241] (3254)

							sulfur oxoacid derivative [CHEBI:33424] (628)

								sulfonic acid derivative [CHEBI:33552] (393)

									arenesulfonate ester [CHEBI:38094] (12)

bromophenol blue [CHEBI:59424] (1)

					halide [CHEBI:37578] (1402)

						organohalogen compound [CHEBI:36684] (976)

							organobromine compound [CHEBI:37141] (138)

bromophenol blue [CHEBI:59424] (1)

ChEBI Compound Accession Identifier:

[CHEBI:59424]

ChEBI Compound Description:

3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 3,5-dibromo-4-hydroxyphenyl groups. It is used as a laboratory indicator, changing from yellow below pH 3 to purple at pH 4.6, and as a size marker for monitoring the progress of agarose gel and polyacrylamide gel electrophoresis. It has also been used as an industrial dye.

ChEBI Compound Identification Number:

59424

ChEBI InChI Value:

InChI=1S/C19H10Br4O5S/c20-12-5-9(6-13(21)17(12)24)19(10-7-14(22)18(25)15(23)8-10)11-3-1-2-4-16(11)29(26,27)28-19/h1-8,24-25H

ChEBI InChIKey Value:

UDSAIICHUKSCKT-UHFFFAOYSA-N

ChEBI Compound Name:

bromophenol blue

ChEBI SMILES Value:

Oc1c(Br)cc(cc1Br)C1(OS(=O)(=O)c2ccccc12)c1cc(Br)c(O)c(Br)c1

ChEBI Substance ID:

93581483

ChEBI URL:

ChemSpider ID:

NS

Ontomatica Chemical Accession Key (OnChAKey):

UDSAIICHUKSCKT_UHFFFAOYSA_N_000_000000

PubChem Compound ID:

8272