Methyl 6-bromopicolinate Chemical Properties

Melting point:

92-96 °C(lit.)

Boiling point:

289.7±20.0 °C(Predicted)

Density 

1.579±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

pka

-1.03±0.10(Predicted)

form 

Crystalline Powder or Needles

color 

White to pale pink to pale brown to yellow

InChI

InChI=1S/C7H6BrNO2/c1-11-7(10)5-3-2-4-6(8)9-5/h2-4H,1H3

InChIKey

SGNCOKUHMXLGAH-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

26218-75-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41

Safety Statements 

26-39

WGK Germany 

3

Hazard Note 

Harmful/Irritant/Keep Cold

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

Methyl 6-bromopicolinate Usage And Synthesis

Chemical Properties

White to off-white solid

Uses

Methyl 6-bromopicolinate, also known as Methyl 6-bromopyridine-2-carboxylate, is a halogenated pyridine derivative that can be used in esterolysis reactions to form 6-Bromopicolinic acid.It can also be used in substitution reactions or cross-couplings to synthesise other pyridine compounds.

Synthesis

The general procedure for the synthesis of methyl 6-bromo-2-pyridinecarboxylate from methanol and 6-bromo-2-pyridinecarboxylic acid is as follows: 1. 6-bromo-2-pyridine carboxylic acid (6.000 g) was dissolved in methanol (180 mL) containing concentrated hydrochloric acid and heated to reflux. 2. Sulfuric acid (2 mL) was added and the reaction continued to reflux for 4 hours. 3. Upon completion of the reaction, the reaction mixture was cooled to about 0°C and concentrated. 4. Ammonia (4.8 mL) was added to the concentrated mixture. 5. The resulting solution was evaporated to give a white solid residue. 6. 6. The white solid was dissolved in a solvent mixture of dichloromethane (100 mL) and brine (100 mL), and the organic layer was separated with sufficient shaking. 7. The organic layer was dried with magnesium sulfate and the solvent was evaporated to give the white solid product methyl 6-bromo-2-pyridinecarboxylate (6.300 g, 98% yield). Product characterization data: 1H NMR (400 MHz, CDCl3) δ 4.00 (3H, s), 7.66-7.74 (2H, m), 8.07-8.13 (1H, m).

References

[1] Patent: WO2003/84917, 2003, A1. Location in patent: Page/Page column 26
[2] Journal of Agricultural and Food Chemistry, 2016, vol. 64, # 18, p. 3533 - 3537
[3] Patent: WO2017/9798, 2017, A1. Location in patent: Page/Page column 92
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 2, p. 722 - 748
[5] Inorganic Chemistry, 2018, vol. 57, # 13, p. 7512 - 7515

Methyl 6-bromopicolinate(26218-75-7)Related Product Information

• 6-BROMO-4-INDAZOLECARBOXYLIC ACID METHYL ESTER
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• methyl 6-chloropyrimidine-4-carboxylate
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• Methyl 6-bromohexanoate
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• 6-CHLORO-2-PICOLINIC ACID METHYL ESTER
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• methyl 6-methylpyridine-2-carboxylate
• Methyl 6-bromo-2-naphthoate
• 6-METHYLPYRAZINE-2-CARBOXYLIC ACID METHYL ESTER
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• Methyl 6-HydroxypyriMidine-4-carboxylate
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• 5-Bromopicolinic acid
• 2-Picolinic acid