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| | Methyl 4-chloropicolinate Basic information |
| | 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) |
| Hazard Codes | Xi | | Risk Statements | 36 | | Safety Statements | 26 | | HazardClass | IRRITANT | | HS Code | 2933399990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2 |
| | 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%).
| | References | [1] Patent: US2008/234332, 2008, A1. Location in patent: Page/Page column 22; 25
[2] Patent: CN105175325, 2017, B. Location in patent: Paragraph 0024; 0025
[3] Patent: WO2008/77188, 2008, A1. Location in patent: Page/Page column 28
[4] Patent: US9533973, 2017, B2. Location in patent: Page/Page column 34
[5] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 8, p. 2512 - 2515 |
| | Methyl 4-chloropicolinate Preparation Products And Raw materials |
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