2,4-DICHLORO-3-AMINO-6-BROMOPYRIDINE

2,4-DICHLORO-3-AMINO-6-BROMOPYRIDINE Property

Boiling point:

301.2±37.0 °C(Predicted)

Density 

1.934±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

-2.02±0.10(Predicted)

Safety

HazardClass 

IRRITANT

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2,4-DICHLORO-3-AMINO-6-BROMOPYRIDINE Chemical Properties,Usage,Production

Synthesis

(d) Synthesis of 3-amino-6-bromo-2,4-dichloropyridine. 3-Amino-2,4-dichloropyridine (500 mg, 3.1 mmol) was dissolved in N,N-dimethylformamide (DMF, 16 mL) and cooled to 0 °C in an ice-water bath. Subsequently, a solution of N-bromosuccinimide (660 mg, 3.7 mmol) in DMF (7 mL) was slowly added dropwise. After 15 min of reaction, the reaction mixture was poured into water and extracted with ethyl acetate (EtOAc, 2×). The organic phases were combined, washed sequentially with water and saturated saline, dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to give a red residue. The residue was dissolved in a mixed solvent of ethyl acetate/hexane with a volume ratio of 1:1, filtered through a silica gel short column, and concentrated again under reduced pressure to give 0.68 g of the title compound in colorless crystalline form (90% yield). 1H NMR (DMSO-d6, 500 MHz): δ 6.10 (s, 2H), 7.69 (s, 1H). Mass spectrum (MS) m/z: 243 ([M+H]+, 81Br), 241 ([M+H]+, 79Br).

References

[1] Journal of Medicinal Chemistry, 2000, vol. 43, # 22, p. 4288 - 4312
[2] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 3, p. 1511 - 1530
[3] MedChemComm, 2016, vol. 7, # 5, p. 1022 - 1032
[4] Patent: US6187777, 2001, B1