5-Ethyl-2-methylpyridine

5-Ethyl-2-methylpyridine
Names
	Other names aldehyde-collidine, MEP, 5-Ethyl-2-picoline
Identifiers
CAS Number	104-90-5 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	109269
ChEMBL	ChEMBL227181;
ChemSpider	21105900;
ECHA InfoCard	100.002.955
EC Number	203-250-0;
PubChem CID	7728;
RTECS number	TJ6825000;
UNII	WG205CGK3Y;
UN number	2300
CompTox Dashboard (EPA)	DTXSID7021861 ;
	InChI InChI=1S/C8H11N/c1-3-8-5-4-7(2)9-6-8/h4-6H,3H2,1-2H3 Key: NTSLROIKFLNUIJ-UHFFFAOYSA-N;
	SMILES CCC1=CN=C(C=C1)C;
Properties
Chemical formula	C8H11N
Molar mass	121.183 g·mol−1
Appearance	colorless liquid
Density	0.9208 g/cm3
Melting point	−70.3 °C (−94.5 °F; 202.8 K)
Boiling point	178 °C (352 °F; 451 K)
Solubility in water	1.2g/100 mL
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H311, H314, H315, H317, H319, H331, H412
Precautionary statements	P260, P261, P264, P270, P271, P272, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P330, P332+P313, P333+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

5-Ethyl-2-methylpyridine is an organic compound with the formula (C₂H₅)(CH₃)C₅H₃N. One of several isomeric pyridines with this formula, this derivative is of interest because it is efficiently prepared from simple reagents and it is a convenient precursor to nicotinic acid, a form of vitamin B₃. 5-Ethyl-2-methylpyridine is a colorless liquid.^[1]

Synthesis and reactions

5-Ethyl-2-methylpyridine is produced by condensation of paraldehyde (a derivative of acetaldehyde) and ammonia:^[2]

4 CH₃CHO + NH₃ → (C₂H₅)(CH₃)C₅H₃N + 4 H₂O

The conversion is an example of a structurally complex compound efficiently made from simple precursors. Under related conditions, the condensation of acetaldehyde and ammonia delivers 2-picoline.

Oxidation of 5-ethyl-2-methylpyridine with nitric acid gives nicotinic acid via the decarboxylation of 2,5-pyridinedicarboxylic acid.^[1]

Toxicity

Like most alkylpyridines, the LD₅₀ of 5-ethyl-2-methylpyridine is modest, being 368 mg/kg (oral, rat).^[1]

References

1 2 3 Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399. ISBN 978-3527306732.
↑ Frank, R. L.; Pilgrim, F. J.; Riener, E. F. (1950). "5-Ethyl-2-Methylpyridine (2-Picoline, 5-ethyl-)". Organic Syntheses. 30: 41. doi:10.15227/orgsyn.030.0041.

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[ullmann-1] 1 2 3 Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399. ISBN 978-3527306732.

[Frank1963-2] Frank, R. L.; Pilgrim, F. J.; Riener, E. F. (1950). "5-Ethyl-2-Methylpyridine (2-Picoline, 5-ethyl-)". Organic Syntheses. 30: 41. doi:10.15227/orgsyn.030.0041.

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