| Identification | More | [Name]
5-Bromo-2-chloronicotinic acid | [CAS]
29241-65-4 | [Synonyms]
5-BROMO-2-CHLORO-3-PYRIDINECARBOXYLIC ACID
5-BROMO-2-CHLORONICOTINIC ACID
5-BROMO-2-CHLOROPYRIDINE-3-CARBOXYLIC ACID
5-Bromo-2-chloronicotinicacid5-Bromo-2-chloronicotinicacid
5-Bromo-2-Chloronicotinic
5-Bromo-2-chloronicotinic acid 97% | [Molecular Formula]
C6H3BrClNO2 | [MDL Number]
MFCD03844847 | [Molecular Weight]
236.45 | [MOL File]
29241-65-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
173-176°C | [Boiling point ]
345.1±42.0 °C(Predicted) | [density ]
1.917±0.06 g/cm3(Predicted) | [storage temp. ]
Keep Cold | [solubility ]
soluble in Methanol | [form ]
Solid | [pka]
1.61±0.25(Predicted) | [color ]
White to Almost white | [InChI]
InChI=1S/C6H3BrClNO2/c7-3-1-4(6(10)11)5(8)9-2-3/h1-2H,(H,10,11) | [InChIKey]
UKNYSJCAGUXDOQ-UHFFFAOYSA-N | [SMILES]
C1(Cl)=NC=C(Br)C=C1C(O)=O | [CAS DataBase Reference]
29241-65-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [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 .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [Hazard Note ]
Irritant/Keep Cold | [HazardClass ]
IRRITANT, KEEP COLD | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white powder | [Synthesis]
Step B. Synthesis of 5-bromo-2-chloronicotinic acid. A mixture of 5-bromo-2-hydroxynicotinic acid (32.9 g, 0.151 mol), dichlorosulfoxide (167 mL), and N,N-dimethylformamide (10.5 mL) was heated to reflux for 4 hours at 70°C. The reaction was carried out with the addition of water. Upon completion of the reaction, the mixture was concentrated, cooled to 0°C, and the reaction was quenched by the slow addition of water to give an off-white precipitate. The precipitate was stirred in water for 1 h and subsequently collected by filtration and dried under vacuum to give 5-bromo-2-chloronicotinic acid (35.5 g, 99% yield). The product can be used directly in the subsequent reaction without further purification or can be purified by recrystallization in hot water. Mass spectrum (electrospray ionization): calculated value C6H3BrClNO2, 234.90; measured value m/z, 236.2 [M + H]+. 1H NMR (acetone-d6): δ 8.66 (d, J = 2.5 Hz, 1H), 8.43 (d, J = 2.5 Hz, 1H). | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 9, p. 2566 - 2569
[2] Patent: US2006/287292, 2006, A1. Location in patent: Page/Page column 26
[3] European Journal of Organic Chemistry, 2010, # 28, p. 5397 - 5401
[4] Synthetic Communications, 1989, vol. 19, # 3and4, p. 553 - 560
[5] Patent: WO2010/136817, 2010, A1. Location in patent: Page/Page column 113 |
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