5-Bromo-2-chloronicotinic acid Chemical Properties

Melting point:

173-176°C

Boiling point:

345.1±42.0 °C(Predicted)

Density 

1.917±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

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 Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

Hazard Note 

Irritant/Keep Cold

HazardClass 

IRRITANT, KEEP COLD

HS Code 

29339900

5-Bromo-2-chloronicotinic acid Usage And Synthesis

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

5-Bromo-2-chloronicotinic acid(29241-65-4)Related Product Information

• 2-Chloronicotinic acid
• BCDMH
• Ethyl 2-(Chlorosulfonyl)acetate
• Chlorobromoisocyanurate
• 3-Bromoanisole
• Folic acid
• Bromine
• Bromochloromethane
• 5-Bromo-2-chloropyridine
• 5-Bromonicotinic acid
• 2-Chloro-3-methyl-5-bromopyridine
• 2-Bromo-5-chloronicotinic acid
• 5-BROMO-6-CHLORONICOTINIC ACID,5-Bromo-6-chloronicotinic acid 97%,5-Bromo-6-chloronicotinic acid ,97%
• (5-BROMO-PYRIDIN-3-YL)-METHANOL
• 5-BROMO-2-CHLORONICOTINIC ACID METHYL ESTER
• 5-BROMO-6-CHLORONICOTINIC ACID METHYL ESTER
• 2-Chloropyridine
• (5-BROMO-2-CHLORO-PYRIDIN-3-YL)-METHANOL