3-BROMO-5-CHLORO-2-HYDROXYPYRIDINE
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3-BROMO-5-CHLORO-2-HYDROXYPYRIDINE
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CAS No:
137628-16-1
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Formula:
C5H3BrClNO
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Chemical Name:
3-BROMO-5-CHLORO-2-HYDROXYPYRIDINE
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Synonyms:
3-BROMO-5-CHLORO-2-HYDROXYPYRIDINE;3-BROMO-5-CHLORO-2-HYDROXYPRIDINE;2-HYDROXY-3-BROMO-5-CHLOROPYRIDINE;3-BROMO-5-CHLOROPYRIDIN-2-OL;3-bromo-5-chloropyridin-2(1H)-one;3-Bromo-5-chloro-2(1H)-pyridinone;3-Bromo-5-chloro-2-pyridone;3-Bromo-5-chloropyridin-2-one
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CAS No:
Characteristics
29.1
1.5
1.91±0.1 g/cm3(Predicted)
277.6±40.0 °C(Predicted)
131.8±25.9 °C
1.629
0.001mmHg at 25°C
Safety Information
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
3-BROMO-5-CHLORO-2-HYDROXYPYRIDINE Use and Manufacturing
A mixture of 5-CHLORO-2-HYDROXYPYRIDINE (20.1 g, 155.4 MMOL) and bromine (11.9 ml) in acetic acid (250 m) was stirred at r. t. for 2 hours. Then, the solvent was evaporated in vacuo and ethyl acetate (600 ML) and saturated sodium bicarbonate (300 ML) were added. The organic layer was washed with saturated sodium bicarbonate (2X200 ML), brine and was dried (NA2SO4) and concentrated to give a solid that was crystallized from hexane/ diethyl ether. The solid 3-bromo-5-chloro-2-hydroxypyridine (21.3 g, 66percent) so obtained was used in the subsequent reaction.To a stirred solution of 5-chloropyridin-2-ol (4 g, 31 mmol) in acetic acid (35 mL) at room temperature was added bromine (2.55 mL, 49.6 mmol) dropwise. After stirring the reaction mixture for overnight at room temperature, water was added and the mixture was extracted twice with ethyl acetate (2 x 150 mL). The organic layer was washed with water, dried over anhydrous sodium sulfate and was concentrated under reduced pressure to afford crude product. The crude product was purified by column chromatography by using silica (100-200 mesh) using 22percent EtOAc-hexane as eluent to afford the 3-bromo-5-chloropyridin-2-ol (4.4 g) as yellow solid.
Computed Properties
Molecular Weight:208.44
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:206.90865
Monoisotopic Mass:206.90865
Topological Polar Surface Area:29.1
Heavy Atom Count:9
Complexity:209
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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3-BROMO-5-CHLORO-2-HYDROXYPYRIDINE
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