| Identification | Back Directory | [Name]
2-Pyrimidinemethanol, 5-bromo- (8CI,9CI) | [CAS]
22433-12-1 | [Synonyms]
5-Bromopyrimidine-2-methanol
(5-bromopyrimidin-2-yl)methal
2-Pyrimidinemethanol, 5-bromo-
(5-Bromo-2-pyrimidinyl)methanol
(5-BroMopyriMidin-2-yl)Methanol
(5-bromopyrimidine-2-yl)methanol
5-Bromo-2-(hydroxymethyl)pyrimidine
2-Pyrimidinemethanol, 5-bromo- (8CI,9CI) | [Molecular Formula]
C5H5BrN2O | [MDL Number]
MFCD16610245 | [MOL File]
22433-12-1.mol | [Molecular Weight]
189.01 |
| Chemical Properties | Back Directory | [Melting point ]
93-94 °C | [Boiling point ]
263.7±20.0 °C(Predicted) | [density ]
1.785±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [pka]
13.23±0.10(Predicted) | [Appearance]
Light yellow to yellow Solid | [InChI]
InChI=1S/C5H5BrN2O/c6-4-1-7-5(3-9)8-2-4/h1-2,9H,3H2 | [InChIKey]
ZRHVXSBXNUJBGF-UHFFFAOYSA-N | [SMILES]
C1(CO)=NC=C(Br)C=N1 |
| Hazard Information | Back Directory | [Uses]
(5-Bromopyrimidin-2-yl)methanol is used to prepare alcohol-?containing benzothiazoles as potent dual-?targeting bacterial DNA supercoiling inhibitors. | [Synthesis]
General procedure for the synthesis of (5-bromopyrimidin-2-yl)methanol from the compound (CAS:1025351-12-5): (Step 4) Methyl (5-bromopyrimidin-2-yl)benzoate (7.30 g, 25.0 mmol) was dissolved in methanol (15 ml), to which a 1N sodium methanol/methanol solution (50.0 ml, 0.500 mmol) was added. The resulting mixture was stirred at room temperature until the deprotection reaction was complete. After completion of the reaction, the solvent was removed by distillation. The obtained residue was purified by silica gel column chromatography (eluent ratio: dichloromethane:methanol = 30:1 to 15:1) to afford the title compound (5-bromopyrimidin-2-yl)methanol (3.58 g, 76% yield). The product was characterized by 1H NMR (CDCl3, 400 MHz): δ 8.80 (s, 2H), 4.82 (d, J=4.0 Hz, 2H), 3.39 (s, 1H). | [References]
[1] Patent: US2015/51395, 2015, A1. Location in patent: Paragraph 1531-1532
[2] Patent: US2016/244451, 2016, A1. Location in patent: Paragraph 0283; 0284; 0285
[3] Synlett, 2008, # 4, p. 543 - 546 |
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