3,5-Lutidine

3,5-Lutidine
Names
	Preferred IUPAC name 3,5-Dimethylpyridine
	Other names 3,5-Lutidine
Identifiers
CAS Number	591-22-0 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	105682
ChemSpider	11077 ;
ECHA InfoCard	100.008.827
EC Number	209-708-6;
PubChem CID	11565;
UNII	6Q4YPZ045V ;
CompTox Dashboard (EPA)	DTXSID5052254;
	InChI InChI=1S/C7H9N/c1-6-3-7(2)5-8-4-6/h3-5H,1-2H3 Key: HWWYDZCSSYKIAD-UHFFFAOYSA-N;
	SMILES CC1=CC(=CN=C1)C;
Properties
Chemical formula	C7H9N
Molar mass	107.156 g·mol−1
Appearance	oily liquid
Density	0.944 g/cm3
Melting point	−6.5 °C (20.3 °F; 266.6 K)
Boiling point	171.9 °C (341.4 °F; 445.0 K)
Acidity (pKa)	6.15
Magnetic susceptibility (χ)	−71.72×10−6 cm3/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H301, H302, H311, H312, H314, H315, H331, H332, H335
Precautionary statements	P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+P310, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P330, P332+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3,5-Lutidine is a heterocyclic organic compound with the formula (CH₃)₂C₅H₃N. It is one of several dimethyl-substituted derivatives of pyridine, all of which are referred to as lutidines. It is a colorless liquid with mildly basic properties and a pungent odor. The compound is a precursor to the drug omeprazole.

3,5-Lutidine is produced industrially by condensation of acrolein, ammonia, and formaldehyde:^[1]

2 CH₂=CHCHO + CH₂O + NH₃ → (CH₃)₂C₅H₃N + 2 H₂O

^ ^a ^b 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.

[Ullmann-1] 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.

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