24484-93-3
- Product Name:Methyl 4-chloropicolinate
- Molecular Formula:C7H6ClNO2
- Purity:99%
- Molecular Weight:171.58
Product Details:
CasNo: 24484-93-3
Molecular Formula: C7H6ClNO2
Purity: 99%
Methyl 4-chloropicolinate Chemical Properties |
Melting point | 50-52°C |
Boiling point | 105-111 °C (Press: 2-3 Torr) |
density | 1.294±0.06 g/cm3 |
storage temp. | Keep in dark place, Sealed in dry, Room Temperature |
solubility | Chloroform (Slightly), Methanol (Slightly) |
form | Solid |
pka | -0.25±0.10 |
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 |
Methyl 4-chloropicolinate Usage And Synthesis |
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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