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3,5-Lutidine

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3,5-Lutidine
Names
Preferred IUPAC name 3,5-Dimethylpyridine
Other names 3,5-Lutidine
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 105682
ChemSpider
ECHA InfoCard 100.008.827 Edit this at Wikidata
EC Number
  • 209-708-6
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H9N/c1-6-3-7(2)5-8-4-6/h3-5H,1-2H3Key: HWWYDZCSSYKIAD-UHFFFAOYSA-N
SMILES
  • CC1=CC(=CN=C1)C
Properties
Chemical formula C7H9N
Molar mass 107.156 g·mol
Appearance oily liquid
Density 0.944 g/cm
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 cm/mol
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
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 , 100 kPa). Infobox references
Chemical compound

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:

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

Biodegradation

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

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. ISBN 978-3-527-30673-2.
  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): 1390–1398. Bibcode:2007EnST...41.1390P. 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. Bibcode:1985JEnvQ..14..580S. 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. Bibcode:1986EnvTC...5..503S. doi:10.1002/etc.5620050601.
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