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Methyl isonicotinate

Product NameMethyl isonicotinate
CAS2459-09-8
MFC7H7NO2
MW137.14
EINECS219-546-8
MOL File2459-09-8.mol

Chemical Properties

Melting point	8-8.5 °C (lit.)
Boiling point	207-209 °C (lit.)
Density	1.161 g/mL at 25 °C (lit.)
vapor pressure	32.2Pa at 25℃
refractive index	n20/D 1.512(lit.)
Flash point	180 °F
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
solubility	Chloroform, Ethyl Acetate
form	Liquid
pka	pK1:3.26(+1) (25°C)
color	Clear orange to brown
Specific Gravity	1.001
Water Solubility	Slightly soluble in water.
BRN	114618
InChI	1S/C7H7NO2/c1-10-7(9)6-2-4-8-5-3-6/h2-5H,1H3
InChIKey	OLXYLDUSSBULGU-UHFFFAOYSA-N
SMILES	COC(=O)c1ccncc1
LogP	0.464 at 25℃
CAS DataBase Reference	2459-09-8(CAS DataBase Reference)
NIST Chemistry Reference	Pyridine-4-carboxylic acid, methyl ester(2459-09-8)
EPA Substance Registry System	4-Pyridinecarboxylic acid, methyl ester (2459-09-8)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36
RIDADR	NA 1993 / PGIII
WGK Germany	3
F	10
Hazard Note	Irritant
TSCA	TSCA listed
HazardClass	CBL
HS Code	29333990
Storage Class	10 - Combustible liquids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Chemical Properties

CLEAR ORANGE TO BROWN LIQUID

Uses

Methyl isonicotinate can be used in:

The preparation of various photosensitizers for applications in dye-sensitized solar cells (DSSCs).
Synthesizing luminophore for luminescent metal-organic framework (MOF).
Nonaqueous redox flow batteries as pyridine-based anolyte material that undergoes two reversible reductions in solutions with Li-ion electrolytes.

Uses

Methyl Isonicotinate induces increased walking and take-off behaviour in western flower thrips, Frankliniella occidentalis.

Uses

Methyl Isonicotinate induces increased walking and take-off behavior in western flower thrips, Frankliniella occidentalis.

Flammability and Explosibility

Not classified

Synthesis

872-85-5

67-56-1

2459-09-8

GENERAL STEPS: A mixture of chlorobrominated resin and K2CO3 in MeOH-H2O (8:2, 3 mL) was placed in a round-bottomed flask equipped with a magnetic stirrer. 4-Pyridinecarboxaldehyde (1 mmol, 1 equiv.) was added to it slowly and the reaction mixture was stirred at room temperature. The progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was filtered and the filtrate was extracted with ether (Et2O). The ether layer was washed sequentially with water, brine, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated. If necessary, the residue was purified by column chromatography on silica gel (60-120 mesh) using a mixture of petroleum ether (PE) and ethyl acetate (EtOAc) (9:1) as eluent.

References

[1] Synthesis, 2010, # 2, p. 276 - 282
[2] Synlett, 2016, vol. 27, # 9, p. 1344 - 1348
[3] Tetrahedron Letters, 2014, vol. 55, # 39, p. 5358 - 5360
[4] Synthetic Communications, 2010, vol. 40, # 2, p. 186 - 195
[5] Synthesis, 2009, # 9, p. 1578 - 1581

Methyl isonicotinate

Chemical Properties

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MSDS

Usage And Synthesis

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