4-Amino-2,6-dibromopyridine Chemical Properties

Melting point:

205-207 °C(Solv: hexane (110-54-3); benzene (71-43-2))

Boiling point:

373.7±37.0 °C(Predicted)

Density 

2.147±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

0.80±0.50(Predicted)

color 

Off-white

InChI

InChI=1S/C5H4Br2N2/c6-4-1-3(8)2-5(7)9-4/h1-2H,(H2,8,9)

InChIKey

NTFZVUOMTODHRO-UHFFFAOYSA-N

SMILES

C1(Br)=NC(Br)=CC(N)=C1

CAS DataBase Reference

39771-34-1

Safety Information

HS Code 

2933399990

4-Amino-2,6-dibromopyridine Usage And Synthesis

Uses

2,6-Dibromo-4-aminopyridine can be used as a pharmaceutical synthesis intermediate.

Synthesis

c) Synthesis of 2,6-dibromopyridin-4-amine: iron powder (1.26 g, 22.56 mmol) was slowly added to a stirring solution of 2,6-dibromo-4-nitropyridine 1-oxide (Preparation 22b, 1.68 g, 5.64 mmol) in acetic acid (16 mL) at 0 °C. The reaction mixture was stirred continuously for 1 hour at room temperature. Upon completion of the reaction, water and ethyl acetate were added to the mixture for extraction. The organic layer was separated and washed sequentially with water, saturated aqueous potassium carbonate solution and brine, followed by drying with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 2,6-dibromo-4-aminopyridine as a white solid (1.35 g, 96% yield).LRMS (m/z): 251/253/255 (M + 1)+.1H NMR (400 MHz, chloroform-d) δ ppm 4.33 (br.s., 2H), 6.68 (s, 2H).

References

[1] Patent: WO2012/41476, 2012, A1. Location in patent: Page/Page column 58-59
[2] Patent: EP2441755, 2012, A1. Location in patent: Paragraph 0174
[3] Patent: US2012/88750, 2012, A1. Location in patent: Page/Page column 22
[4] Tetrahedron Letters, 2011, vol. 52, # 44, p. 5728 - 5732
[5] Chemistry - A European Journal, 2013, vol. 19, # 41, p. 13745 - 13760

4-Amino-2,6-dibromopyridine(39771-34-1)Related Product Information

• 2,6-Dibromo-4-nitropyridine N-oxide
• 4-Amino-2,6-dibromo-3-nitropyridine
• 4-Amino-2-bromopyridine
• 2,6-Dibromopyridine
• 2,6-DIBROMO-4-NITRO-PYRIDINE
• 4-Amino-2,6-dibromopyridine