3,5-Lutidine

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, noxious odor. The compound is a precursor to the drug omeprazole.

3,5-Lutidine
Names
Preferred IUPAC name
3,5-Dimethylpyridine
Other names
3,5-Lutidine
Identifiers
3D model (JSmol)
105682
ChemSpider
ECHA InfoCard 100.008.827
EC Number
  • 209-708-6
UNII
Properties
C7H9N
Molar mass 107.156 g·mol−1
Appearance Clear 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[1]
-71.72·10−6 cm3/mol
Hazards
GHS pictograms
GHS Signal word Danger
H226, H301, H302, H311, H312, H314, H315, H318, H331, H332, H335
P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+310, P301+312, P301+330+331, P302+352, P303+361+353, P304+312, P304+340, P305+351+338, P310, P311, P312, P321, P322
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

It is produced industrially by condensation of acrolein, ammonia, and formaldehyde.[1]

Biodegradation

The biodegradation of pyridines proceeds via multiple pathways.[2] Although pyridine is an excellent source of carbon, nitrogen, and energy for certain microorganisms, methylation significantly retards degradation of the pyridine ring.[3][4]

Safety

The LD50 is 200 mg/kg (oral, rats).

See also

References

  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.
  2. Philipp, Bodo; Hoff, Malte; Germa, Florence; Schink, Bernhard; Beimborn, Dieter; Mersch-Sundermann, Volker (2007). "Biochemical Interpretation of Quantitative Structure-Activity Relationships (QSAR) for Biodegradation of N-Heterocycles: A Complementary Approach to Predict Biodegradability". Environmental Science & Technology. 41 (4): 1390–8. doi:10.1021/es061505d. PMID 17593747.
  3. Sims, G. K.; Sommers, L.E. (1985). "Degradation of pyridine derivatives in soil". Journal of Environmental Quality. 14 (4): 580–584. doi:10.2134/jeq1985.00472425001400040022x.
  4. Sims, G. K.; Sommers, L.E. (1986). "Biodegradation of Pyridine Derivatives in Soil Suspensions". Environmental Toxicology and Chemistry. 5 (6): 503–509. doi:10.1002/etc.5620050601.
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