| Identification | Back Directory | [Name]
4-Bromo-2-pyridinemethanol | [CAS]
131747-45-0 | [Synonyms]
4-BROMO-2-PYRIDINEMETHANOL
4-Bromopyridine-2-methanol
(4-BroMo-2-pyridyl)Methanol
4-Bromopyridine-2-methano...
2-Pyridinemethanol, 4-bromo-
(4-Bromopyridin-2-yl)methanol
4-BroMo-2-pyridineMethanol HCl
4-Bromo-2-(hydroxymethyl)pyridine
1-(4'-bromopyridin-2'-yl)methanol
4-Bromo-2-pyridinemethanol ISO 9001：2015 REACH | [Molecular Formula]
C6H6BrNO | [MDL Number]
MFCD09800557 | [MOL File]
131747-45-0.mol | [Molecular Weight]
188.02 |
| Chemical Properties | Back Directory | [Melting point ]
52.0 to 56.0 °C | [Boiling point ]
105°C/0.5mmHg(lit.) | [density ]
1.668±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder to lump | [pka]
13.09±0.10(Predicted) | [color ]
White to Light yellow to Light orange |
| Hazard Information | Back Directory | [Uses]
4-Bromo-2-pyridinemethanol is used as a reagent to synthesize bisphosphonate derivatives, compounds that inhibit farnesyl pyrophosphate synthase (an important enzyme in isoprenoid biosynthesis). | [Synthesis]
Step 1: Methyl 4-bromopyridine-2-carboxylate (990 mg, 4.58 mmol) and ethanol (250 mL) were added to a 250 mL reaction flask. Sodium borohydride (380 mg, 10 mmol) was added slowly in batches under stirring conditions. The reaction mixture was stirred at room temperature and under nitrogen protection for 18 hours. After completion of the reaction, 5 mL of acetone was added to the system and stirring was continued for 15 minutes. The reaction solution was filtered, and the filtrate was concentrated and extracted by adding ethyl acetate and water to separate the organic and aqueous phases. The organic phase was dried and concentrated to give 2-hydroxymethyl-4-bromopyridine (yellow liquid, 760 mg, 88% yield), and the crude product was used directly in the next reaction. (MS data: [M + 1] 187.9) | [References]
[1] Patent: WO2012/78915, 2012, A1. Location in patent: Page/Page column 95-96
[2] Patent: EP3150592, 2017, A1. Location in patent: Paragraph 0201; 0202; 0203
[3] Journal of Medicinal Chemistry, 1997, vol. 40, # 18, p. 2866 - 2875 |
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