3,5-Lutidine

3,5-Lutidine

Names
Preferred IUPAC name 3,5-Dimethylpyridine
Other names 3,5-Lutidine
Identifiers
CAS Number	591-22-0  Y
3D model (JSmol)	Interactive image
Beilstein Reference	105682
ChemSpider	11077  Y
ECHA InfoCard	100.008.827
EC Number	209-708-6
PubChem CID	11565
UNII	6Q4YPZ045V  Y
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 [1]
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

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

• 2,6-Lutidine
• 2,4-Lutidine

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.