Methyl 6-amino-3-bromopicolinate Chemical Properties

Boiling point:

333.4±37.0 °C(Predicted)

Density 

1.662±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

1.12±0.10(Predicted)

form 

solid

color 

Off white

InChI

InChI=1S/C7H7BrN2O2/c1-12-7(11)6-4(8)2-3-5(9)10-6/h2-3H,1H3,(H2,9,10)

InChIKey

YJUKTIBOUBUOJH-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)=NC(N)=CC=C1Br

Safety Information

Hazard Codes 

Xi

HS Code 

2933399990

Methyl 6-amino-3-bromopicolinate Usage And Synthesis

Synthesis

General procedure for the synthesis of methyl 6-amino-3-bromopyridine-2-carboxylate and methyl 5-bromo-6-aminopyridine-2-carboxylate from methyl 6-aminopyridine-2-carboxylate: (d) Synthesis of methyl 6-amino-5-bromopyridine-2-carboxylate: to a solution of methyl 6-aminopyridine-2-carboxylate (10 g, 66.0 mmol) in chloroform (450 mL) was slowly added a solution of bromine (3.4 mL, 66.0 mmol) in chloroform (100 mL) at room temperature, and the reaction mixture was stirred for 40 hours. After completion of the reaction, the reaction mixture was diluted with chloroform and washed sequentially with saturated sodium thiosulfate solution and water. The organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using ethyl acetate/hexane as eluent to afford methyl 6-amino-3-bromopyridine-2-carboxylate as a yellow solid (3.3 g, 22% yield). Mass spectrum (ESI) m/e: 231.0 [M+H]+. 1H NMR (CDCl3, 400MHz): δ (ppm) = 7.76 (d, J = 7.88Hz, 1H), 7.34 (d, J = 7.92Hz, 1H), 5.23 (s, 2H), 3.94 (s, 3H). d) Isolation of methyl 6-amino-3-bromopyridine-2-carboxylate: In step d) above, the isomer methyl 6-amino-3-bromopyridine-2-carboxylate (3.0 g, 19% yield) was also isolated as a by-product. Mass spectrum (ESI) m/e: 231.2 [M+H]+. 1H NMR (CDCl3, 400MHz): δ (ppm) = 7.60 (d, J = 8.72Hz, 1H), 6.47 (d, J = 7.88Hz, 1H), 4.71 (s, 2H), 3.94 (s, 3H).

References

[1] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633
[2] Organic Process Research and Development, 2010, vol. 14, # 1, p. 263 - 271
[3] Tetrahedron Letters, 2010, vol. 51, # 38, p. 5035 - 5037
[4] Patent: US2011/190269, 2011, A1. Location in patent: Page/Page column 61-62
[5] Patent: WO2011/92272, 2011, A1. Location in patent: Page/Page column 129; 130

Methyl 6-amino-3-bromopicolinate(178876-83-0)Related Product Information

• 6-AMINOPICOLINIC ACID METHYL ESTER
• (3-bromopyridin-2-yl)methanol
• 4-Chlorophenethylamine
• 3-BROMOPYRIDINE-2-CARBOXYLIC ACID
• Methyl 6-amino-3-bromopicolinate