| Identification | Back Directory | [Name]
2-BROMORESORCINOL | [CAS]
6751-75-3 | [Synonyms]
2-Bromoresorcinol 95%
2-BroMo-1,3-benzenediol
1,3-Benzenediol, 2-bromo-
2-BroMo-1,3-dihydroxybenzene | [Molecular Formula]
C6H5BrO2 | [MDL Number]
MFCD07779241 | [MOL File]
6751-75-3.mol | [Molecular Weight]
189.01 |
| Chemical Properties | Back Directory | [Melting point ]
96-103℃ | [Boiling point ]
235.3±20.0℃ (760 Torr) | [density ]
1.844±0.06 g/cm3 (20 ºC 760 Torr) | [Fp ]
96.1±21.8℃ | [storage temp. ]
2-8°C | [solubility ]
soluble in Methanol | [form ]
powder to crystaline | [pka]
7.91±0.10(Predicted) | [color ]
White to Yellow to Orange | [InChI]
InChI=1S/C6H5BrO2/c7-6-4(8)2-1-3-5(6)9/h1-3,8-9H | [InChIKey]
UOLPZAPIFFZLMF-UHFFFAOYSA-N | [SMILES]
C1(O)=CC=CC(O)=C1Br |
| Hazard Information | Back Directory | [Uses]
2-Bromoresorcinol is a key intermediate in the treatment of hepatitis C, specifically clopipvir hydrochloride, a pan-genotypic NS5A replication complex inhibitor that can be used in combination with sofosbuvir for the treatment of chronic hepatitis C in adults. Therefore, the development of 2-bromocatechol has a promising market prospect. | [Synthesis]
To 500 ml four-necked bottle successively added 170 g of toluene and 9.4 g of tert-butylamine, cooled down to -30 ℃, 10.4 g of bromine slowly added dropwise, drop after drop, and then cooled down to -60 ℃, dropwise addition of dichloromethane solution of | [Properties and Applications]
The cyclocondensation of 2-bromoresorcinol with some aldehydes proceeds in acetonitrile-CF3SO3H to give cyclic tetramers with high stereoselectivity. 2-bromoresorcinol, C6H5BrO2, are essentially planar and possess normal geometrical parameters. The crystal packing is influenced by O-H...O and O-H...O/Br hydrogen bonds and pi-pi stacking interactions, resulting in a distinctive high-symmetry structure containing R(4)(4)(8) rings and helical C(2) chains[1-2].
| [References]
[1] Peter Kirsop, William T A Harrison, John M D Storey. “1-Bromo-2,6-dihydroxybenzene containing R(4)(4)(8) rings and C(2) helices.” Acta crystallographica. Section C, Crystal structure communications 60 Pt 5 (2004): o353-5.
[2] Osamu Morikawa. “Trifluoromethanesulfonic acid-catalyzed synthesis of resorcinarenes: Cyclocondensation of 2-bromoresorcinol with aldehydes.” Synthesis-Stuttgart 40 1 (2002): 761–765.
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