ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Pyridine derivatives 2-Bromopyridine-4-methanol

2-Bromopyridine-4-methanol

Product Name2-Bromopyridine-4-methanol
CAS118289-16-0
MFC6H6BrNO
MW188.02
EINECS663-333-6
MOL File118289-16-0.mol

Chemical Properties

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
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 Information

Hazard Codes	Xi,Xn
Risk Statements	36/37/38-22
Safety Statements	26-36-37-22
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

MSDS

Provider	Language
ALFA	English

Usage And Synthesis

Chemical Properties

2-Bromopyridine-4-methanol is a white to brown powder, it is stable under normal conditions.

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

66572-56-3

118289-16-0

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

2-Bromopyridine-4-methanol

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

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