2,4-Lutidine

2,4-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 has few uses.

2,4-Lutidine
Names
Preferred IUPAC name
2,4-Dimethylpyridine
Other names
2,4-Lutidine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.261
EC Number
  • 203-586-8
UNII
  • InChI=1S/C7H9N/c1-6-3-4-8-7(2)5-6/h3-5H,1-2H3
    Key: JYYNAJVZFGKDEQ-UHFFFAOYSA-N
  • CC1=CC(=NC=C1)C
Properties
C7H9N
Molar mass 107.156 g·mol−1
Appearance Clear oily liquid
Density 0.9273 g/cm3
Melting point −64 °C (−83 °F; 209 K)
Boiling point 158.5 °C (317.3 °F; 431.6 K)
-71.72·10−6 cm3/mol
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
Warning
H226, H302, H312, H332
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P312, P322, P330, P363, P370+P378, P403+P235, P501
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 extraction from coal tars.[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).[1]

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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