Dimethyl 2-bromo-2,6-pyridinedicarboxylate Chemical Properties

Melting point:

176 °C

Boiling point:

369.6±37.0 °C(Predicted)

Density 

1.569±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-2.40±0.10(Predicted)

Appearance

White to light brown Solid

InChI

InChI=1S/C9H8BrNO4/c1-14-8(12)6-3-5(10)4-7(11-6)9(13)15-2/h3-4H,1-2H3

InChIKey

WYROXHCDUWIUMW-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)=NC(C(OC)=O)=CC(Br)=C1

Safety Information

Safety Statements 

24/25

HS Code 

29333990

Dimethyl 2-bromo-2,6-pyridinedicarboxylate Usage And Synthesis

Synthesis

The general procedure for the synthesis of pyridine 4-bromo-2,6-dicarboxylic acid methyl ester from 4-oxo-1,4-dihydro-2,6-pyridinedicarboxylic acid was as follows: compound 1 was prepared by a modified method from literature [29]. Tribenzoic acid monohydrate (2.20 g, 10.9 mmol) and phosphorus pentabromide (23.4 g, 54.3 mmol, 5 eq.) were heated to 90 °C under nitrogen protection and the reaction was maintained for 2 hours. Upon completion of the reaction, the dark red melt was cooled to room temperature and dissolved by addition of chloroform (25 mL). The reaction mixture was filtered and the filtrate was cooled in an ice bath (0 °C) and methanol (90 mL) was added slowly to promote crystallization. Crystallization was induced by scraping and the resulting crystalline solid was collected by vacuum filtration and dried under vacuum to afford compound 1 as a white crystalline solid (2.82 g, 86% yield).1H NMR (300 MHz, CDCl3) δ 8.45 (s, 2H), 4.02 (s, 6H).

References

[1] Journal of Inorganic Biochemistry, 2016, vol. 162, p. 253 - 262
[2] Organic Letters, 2011, vol. 13, # 3, p. 442 - 445
[3] Chemical Communications, 2012, vol. 48, # 80, p. 10025 - 10027
[4] Chemical Communications, 2014, vol. 50, # 68, p. 9665 - 9668
[5] Dalton Transactions, 2017, vol. 46, # 16, p. 5229 - 5239

Dimethyl 2-bromo-2,6-pyridinedicarboxylate(162102-79-6)Related Product Information

• 6-FORMYL-2-PYRIDINE CARBOXYLIC ACID METHYL ESTER
• METHYL-6-HYDROXYMETHYL-2-CARBOXYLATE PYRIDINE
• 4-Bromo-2,6-diformylpyridine
• 4-BROMOPYRIDINE-2-CARBALDEHYDE
• 2,6-Pyridinedicarboxylic acid monomethyl ester
• Dimethyl 2,6-Pyridinedicarboxylate
• 4-BROMOPYRIDINE-2,6-DICARBOXYLIC ACID
• 4-BROMO-6-METHYL-PYRIDINE-2-CARBALDEHYDE
• 4-BROMO-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER
• 4-Bromopyridine-2,6-dimethanol
• 4-Bromo-2-pyridinemethanol
• Dimethyl 2-bromo-2,6-pyridinedicarboxylate
• Diethyl 4-bromopyridine-2,6-dicarboxylate
• 4-Bromopyridine-2-carboxylic acid
• 4-Bromo-2,6-dimethylpyridine