3-BROMOPYRIDINE-2-CARBOXYLIC ACID
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3-BROMOPYRIDINE-2-CARBOXYLIC ACID
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CAS No:
30683-23-9
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Formula:
C6H4BrNO2
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Chemical Name:
3-BROMOPYRIDINE-2-CARBOXYLIC ACID
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Synonyms:
3-BROMOPICOLINIC ACID;3-BROMOPYRIDIN-2-YLCARBOXYLIC ACID;3-BROMOPYRIDINE-2-CARBOXYLIC ACID;3-BROMO-2-PYRIDINECARBOXYLIC ACID;IFLAB-BB F1926-0036;3-bromo-2-pyridine carboxlic acid;3-Bromo-2-picolinic acid;3-Bromo-pyridine-2-carboxylic Aci
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CAS No:
Characteristics
50.2
1.4
Solid
1.813
141-1440C
315.7°C at 760 mmHg
144.8±23.7 °C
1.617
Room temperature.
Safety Information
IRRITANT
22
Xi,Xn
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
3-BROMOPYRIDINE-2-CARBOXYLIC ACID Use and Manufacturing
3-Bromopicolinic acid (1.93 g, 8.65 mmol) was heated to reflux in thionyl chloride (30.9 g, 259 mmol) for one hour. The solvent was removed in vacuo and the residue azeotroped with toluene. The residue was dissolved in methanol and heated to reflux for 3 hours. The solvent was removed in vacuo and the residue taken up into ethyl acetate. The organic extract was washed with saturated sodium bicarbonate solution, dried over MgSO4 and evaporated. The residue was purified by flash column chromatography on silica, eluting with 35% ethyl acetate/isohexane, to yield methyl 3-bromopyridine-2-carboxylate as an oil (1.33g, EPO General procedure: To a solution under argon of the appropriate acid (1 equiv.) in anhydrous benzene (3 mL/1 mmol of acid) was added oxalyl chloride (1.5 equiv.), followed by N, N-dimethylformamide (2 drops). When gas evolution had ceased (30 min.), the reaction mixture was concentrated under vacuum to afford the crude acyl chloride, which was used without further purification. Triethylamine (3 equiv.) was added to a solution under argon of the appropriate amine (1 equiv.) in anhydrous CH2Cl2 (2 mL / 1 mmol of acid). The acyl chloride (1 equiv.) in anhydrous CH2Cl2 (2 mL / 1 mmol of acid) was added dropwise to this mixture. After 60 min, the reaction mixture was concentrated and the crude product was directly purified by chromatography on silica gel to yield the expected amide.
Computed Properties
Molecular Weight:202.01
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:200.94254
Monoisotopic Mass:200.94254
Topological Polar Surface Area:50.2
Heavy Atom Count:10
Complexity:140
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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3-BROMOPYRIDINE-2-CARBOXYLIC ACID
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