Methyl 5-bromo-6-chloropyridine-3-carboxylate Chemical Properties

Melting point:

75-77°C

Boiling point:

279.2±35.0 °C(Predicted)

Density 

1.684

refractive index 

1.568

storage temp. 

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

solubility 

Chloroform (Slightly), Methanol (Slightly), Water (Slightly)

pka

-2.84±0.10(Predicted)

form 

Solid

color 

White to Off-White

InChI

InChI=1S/C7H5BrClNO2/c1-12-7(11)4-2-5(8)6(9)10-3-4/h2-3H,1H3

InChIKey

WINGWVOUOFMOJQ-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=C(Br)C=C1C(OC)=O

CAS DataBase Reference

78686-77-8

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2933399990

Methyl 5-bromo-6-chloropyridine-3-carboxylate Usage And Synthesis

Uses

Methyl 5-Bromo-6-chloronicotinate can be used to treat diseases related to S1PR1.

Synthesis

Step 1: Synthesis of methyl 5-bromo-6-chloronicotinate (61). A mixture of 5-bromo-6-chloronicotinic acid (60) (0.2 g, 0.84 mmol), potassium carbonate (K2CO3) (0.3 g, 2.1 mmol) and iodomethane (0.178 g, 1.2 mmol) in N,N-dimethylformamide (DMF) (10 mL) was stirred for 16 h at 0 °C and subsequently raised to room temperature. Upon completion of the reaction, the reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (EtOAc) (2 x 20 mL). The organic phases were combined and washed sequentially with saturated aqueous sodium bicarbonate (NaHCO3) (20 mL) and brine (2 x 20 mL), dried over anhydrous sodium sulfate (Na2SO4) and concentrated to afford the target product methyl 5-bromo-6-chloronicotinate (61) (0.2 g, 94.7% yield).

References

[1] Patent: WO2017/4608, 2017, A1. Location in patent: Paragraph 0183

Methyl 5-bromo-6-chloropyridine-3-carboxylate(78686-77-8)Related Product Information

• Kresoxim-methyl
• 3-Bromoanisole
• Methyl formate
• Methylparaben
• Methyl 6-chloronicotinate
• METHYL 2-CHLORONICOTINATE
• RESMETHRIN
• Methyl acrylate
• Methanol
• Basic Violet 1
• Chlorobromoisocyanurate
• CHLORODIBROMOMETHANE
• 1-Bromo-3-chloro-5,5-dimethylhydantoin
• Methyl nicotinate
• Acetonitrile
• Methyl 5-bromonicotinate
• METHYL 5-BROMO-2-CHLOROPYRIDINE-3-CARBOXYLATE
• Methyl