3,5-Lutidine

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3,5-Lutidine
3,5-Lutidine.svg
Names
Preferred IUPAC name
3,5-Dimethylpyridine
Other names
3,5-Lutidine
Identifiers
3D model (JSmol)
105682
ChemSpider
ECHA InfoCard 100.008.827 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-708-6
PubChem CID
UNII
  • InChI=1S/C7H9N/c1-6-3-7(2)5-8-4-6/h3-5H,1-2H3
    Key: HWWYDZCSSYKIAD-UHFFFAOYSA-N
  • CC1=CC(=CN=C1)C
Properties
C7H9N
Molar mass 107.156 g·mol−1
Appearanceoily 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 labelling:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg
Danger
H226, H301, H302, H311, H312, H314, H315, H331, H332, H335
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).

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.

Contents

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

Related Research Articles

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5
H
4
NH(O)
. It is a colourless solid. It is well known to form hydrogen bonded dimers and it is also a classic case of a compound that exists as tautomers.

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<span class="mw-page-title-main">Bromoxynil</span> Chemical compound

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<span class="mw-page-title-main">2-Chloropyridine</span> Chemical compound

2-Chloropyridine is an organohalide with the formula C5H4ClN. It is a colorless liquid that is mainly used to generate fungicides and insecticides in industry. It also serves to generate antihistamines and antiarrythymics for pharmaceutical purposes.

<span class="mw-page-title-main">2,4-Lutidine</span> Chemical compound

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.

<span class="mw-page-title-main">5-Ethyl-2-methylpyridine</span> Chemical compound

5-Ethyl-2-methylpyridine is an organic compound with the formula (C2H5)(CH3)C5H3N. One of several isomeric pyridines with this formula, this derivative is of interest because it is efficiently prepared from simple reagents and it is a convenient precursor to nicotinic acid, a form of vitamin B3. 5-Ethyl-2-methylpyridine is a colorless liquid.

References

  1. 1 2 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.
  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. doi:10.1002/etc.5620050601.