Methyl 4-chloropicolinate Chemical Properties

Melting point:

50-52

Boiling point:

105-111 °C(Press: 2-3 Torr)

Density 

1.294±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

-0.25±0.10(Predicted)

color 

Off-White to Beige

InChI

InChI=1S/C7H6ClNO2/c1-11-7(10)6-4-5(8)2-3-9-6/h2-4H,1H3

InChIKey

VTENWIPSWAMPKI-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

24484-93-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

HazardClass 

IRRITANT

HS Code 

2933399990

Methyl 4-chloropicolinate Usage And Synthesis

Chemical Properties

Brown Solid

Uses

Methyl 4-Chloropicolinate (cas# 24484-93-3) is a compound useful in organic synthesis.

Production Methods

The starting material 2-picolinic acid was treated with SOCl2 to generate 4-chloropicolinoyl chloride, and then esterification with MeOH resulted in the formation of methyl 4-chloropicolinate.

Synthesis Reference(s)

Synthetic Communications, 26, p. 2017, 1996 DOI: 10.1080/00397919608003557

Synthesis

To a suspension of 4-chloropyridine-2-carboxylic acid (4.5 g, 29.0 mmol) in methylene chloride (120 mL) was added oxalyl chloride (3.0 mL, 1.2 eq) under Ar2. The reaction was cooled to 0° C., and 500 uL of DMF was added. A large amount of gas was generated in situ. The reaction was stirred at room temperature for 1.5 h and then concentrated. Dry MeOH (50 mL) was added to the crude acyl chloride residue. The reaction was stirred at room temperature for 0.5 h, then quenched with NaHCO3 (5%) to neutral, extracted with EtOAc, and washed with brine. The combined organics were dried over MgSO4, filtered, and concentrated in vacuo to give 5.0 g of a crude solid, which was triturated with 5% EtOAc/hexane to give Methyl 4-chloropicolinate as a light yellow solid (4.5 g, 90%).

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