| Identification | More | [Name]
2-Bromopyridine-4-methanol | [CAS]
118289-16-0 | [Synonyms]
2-BROMO-4-(HYDROXYMETHYL)PYRIDINE
2-BROMO-4-PYRIDINE METHANOL
(2-BROMO-PYRIDIN-4-YL)-METHANOL
2-BROMOPYRIDINE-4-METHANOL
RARECHEM AL BD 1524
2-Bromopyridine-4-methanol ,96% | [EINECS(EC#)]
663-333-6 | [Molecular Formula]
C6H6BrNO | [MDL Number]
MFCD04039313 | [Molecular Weight]
188.02 | [MOL File]
118289-16-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
58-61°C | [Boiling point ]
316.6±27.0 °C(Predicted) | [density ]
1.668±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
solid | [pka]
13.06±0.10(Predicted) | [color ]
White | [Detection Methods]
HPLC,NMR | [BRN ]
4244047 | [InChI]
InChI=1S/C6H6BrNO/c7-6-3-5(4-9)1-2-8-6/h1-3,9H,4H2 | [InChIKey]
IQNUGAFIKDRYRP-UHFFFAOYSA-N | [SMILES]
C1(Br)=NC=CC(CO)=C1 | [CAS DataBase Reference]
118289-16-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS05,GHS07 | [Signal word ]
Danger | [Hazard statements ]
H302-H315-H318-H335 | [Precautionary statements ]
P280-P301+P312+P330-P302+P352-P305+P351+P338+P310 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
1 | [HazardClass ]
IRRITANT | [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Dam. 1
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
White to brown powder | [Uses]
2-Bromo-4-hydroxymethylpyridine is used to synthesize aza- and diazabiphenyl analogs of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824). It is also used to N3/8-disubstituted 3,8-diazabicyclo[3.2.1]octane analogues of 3,8-bis[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl-piperazine with antiproliferative properties. | [Health Hazard]
Contact with 2-Bromopyridine-4-methanol causes skin irritation and serious eye irritation.
| [Synthesis]
General procedure for the synthesis of 2-bromo-4-pyridinemethanol from 2-bromo-4-pyridinecarboxylic acid: To a solution of tetrahydrofuran (30 mL) containing 2-bromo-4-pyridinecarboxylic acid (2 g, 9.9 mmol, 1.0 eq.) was added drop-wise the boron trifluoride ether compound (4.18 g, 29.7 mmol, 3.0 eq.) at 0 °C. The reaction mixture was stirred at room temperature for 3 hours. Upon completion of the reaction, the reaction mixture was transferred to ice water and the product was extracted with ethyl acetate. The organic layers were combined, washed with brine solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 2-bromo-4-pyridine methanol (1.4 g, 75.21% yield). Mass spectrum (electrospray): m/z 189.65 [M]+. | [References]
[1] Patent: WO2018/71794, 2018, A1. Location in patent: Paragraph 00983; 00984
[2] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[3] Journal of Medicinal Chemistry, 1997, vol. 40, # 18, p. 2866 - 2875
[4] Patent: US2005/54654, 2005, A1. Location in patent: Page/Page column 36
[5] Patent: EP2098517, 2009, A1. Location in patent: Page/Page column 32 |
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