2,6-Lutidine

2,6-Lutidine Basic information
Chemical Properties Usage Preparation Category Toxicity grade Acute toxicity Flammability hazard characteristics Storage Fire extinguishing agents
Product Name:2,6-Lutidine
Synonyms:FEMA 3540;FEMA NUMBER 3540;DIMETHYLPYRIDINE(2,6-);26L;2,6-LUTIDINE;2 6-DIMETHYLPYRIDINE 99+%;2,6-LUTIDINE, REDISTILLED, 99+%;2 6-LUTIDINE REAGENTPLUS(TM) 99%
CAS:108-48-5
MF:C7H9N
MW:107.15
EINECS:203-587-3
Product Categories:Biochemistry;Reagents for Oligosaccharide Synthesis;pyridine Flavor;Pyridines;Aromatics;Heterocycles;Nitrogen cyclic compounds;Organics;Pyridines derivates;Heterocycle-Pyridine series;K00001
Mol File:108-48-5.mol
2,6-Lutidine Structure
2,6-Lutidine Chemical Properties
Melting point ?6 °C (lit.)
Boiling point 143-145 °C (lit.)
density 0.92 g/mL at 25 °C (lit.)
vapor pressure 5.5 hPa (20 °C)
FEMA 3540 | 2,6-DIMETHYLPYRIDINE
refractive index n20/D 1.497(lit.)
Fp 92 °F
storage temp. −20°C
solubility Chloroform (Soluble), Methanol (Slightly)
form Liquid
pka6.65(at 25℃)
color Clear
Odorat 1.00 % in dipropylene glycol. nutty amine woody bready cocoa oily
Odor Typenutty
Water Solubility 40 g/100 mL (20 ºC)
Sensitive Hygroscopic
Merck 14,5616
JECFA Number1317
BRN 105690
Stability:Stable. Flammable. Incompatible with strong oxidizing agents, acid chlorides, acids, chloroformates. Protect from moisture.
LogP0.12 at 25℃
CAS DataBase Reference108-48-5(CAS DataBase Reference)
NIST Chemistry ReferencePyridine, 2,6-dimethyl-(108-48-5)
EPA Substance Registry System2,6-Dimethylpyridine (108-48-5)
Safety Information
Hazard Codes Xn,F,Xi
Risk Statements 10-22-36/37/38-20/21/22
Safety Statements 26-36/37-16-36-36/37/39
RIDADR UN 1993 3/PG 3
WGK Germany 3
RTECS OK9700000
8
Hazard Note Irritant/Flammable
TSCA Yes
HazardClass 3
PackingGroup III
HS Code 29333999
Hazardous Substances Data108-48-5(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 400 mg/kg LD50 dermal Rabbit > 1000 mg/kg
MSDS Information
ProviderLanguage
2,6-Dimethylpyridine English
SigmaAldrich English
ACROS English
ALFA English
2,6-Lutidine Usage And Synthesis
Chemical PropertiesColorless oily liquid, melting point-5.8℃, boiling point 144℃(139-141℃,145.6-145.8℃), density 0.9252(20/4℃), refractive index 1.4977, flash point 33℃, soluble in dimethyl formamide, tetrahydrofuran, cold water, hot water, ethanol and ether, with mixed odor of Pyridine and mint.
Usage2,6-Lutidine is widely used in organic synthesis as a raw material and solvent. In Pharmaceutical industry, it can be used for the production of antiatherosclerotic pyridinolcarbamate. It can also be used for the production of Cortisone acetate, hydrocortisone, niacin, lobeline and stilbazium iodide which is an anthelmintic and effective for the worm, fasciolopsis buski, whipworm, pinworm and so on. In addition, 2,6-Lutidine can be used as an auxiliaries for Pesticides, dyes, dyeing and printing and used as resin and rubber accelerator,  intermediate of hot oil stabilizer.  It  can be oxidized to produce Dimethyl pyridine acid, which can be used as the stabilizer for hydrogen peroxide and acetic acid and used to synthesize lobelidine. 2,6-Lutidine is used as various kinds of nutty essence and cocoa, coffee, meat, bread and vegetable typed essence. It is also used to synthesize drugs for the treatment and first-aid of hypertension.
Preparation2,6-Lutidine is obtained through the separation of β-methylpyridine which is a recycled product of coal coking byproduct.
Categoryflammable liquid
Toxicity gradehigh toxic
Acute toxicityoral – rat LD50: 400mg/kg
Flammability hazard characteristicsflammable in case of fire, high temperature and oxidant, releasing toxic nitrogen oxides in case of heat.
StorageVentilated and dry warehouse with low temperature, separated from acids.
Fire extinguishing agentsDry powder, dry sand, carbon dioxide, foam.
Chemical Properties2,6-Dimethylpyridine has a powerful and diffusive minty-tarry odor. It has also been described to have the odor of pyridine and peppermint
Chemical PropertiesColorless to yellow liquid
OccurrenceReported found in bread, tea, peppermint oil, cheeses, chicken, beef, pork, beer, sherry, whiskies, cocoa, coffee, tea, oatmeal, rice bran, buckwheat and malt.
UsesIsolated from the basic fraction of coal tar. A semi-volatile compound in tobacco.
Uses2,6-Lutidine is used as a solvent in organic synthesis and as a sterically hindered mild base. It is also used as a vulcanization accelerator for dyes, resins and rubber. It also acts as a food additive.
DefinitionChEBI: A member of the class of methylpyridines that is pyridine carrying methyl substituents at positions 2 and 6.
Taste threshold valuesTaste characteristics at 20 ppm: nutty, coffee, cocoa, musty, bready and meaty
Synthesis Reference(s)Organic Syntheses, Coll. Vol. 2, p. 214, 1943
Tetrahedron Letters, 17, p. 383, 1976 DOI: 10.1016/S0040-4039(00)93738-9
General DescriptionA colorless liquid with a peppermint odor. Flash point 92°F. Less dense than water. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion. Used to make other chemicals.
Air & Water ReactionsHighly flammable. Soluble in water.
Reactivity Profile2,6-Lutidine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
Health HazardInhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
Flammability and ExplosibilityFlammable
SynthesisSynthesis from ethyl acetoacetate, formaldehyde and ammonia; isolated from basic fraction of coal tar
Purification MethodsLikely contaminants include 3-and 4-picoline (similar boiling points). However, they are removed by using BF3, with which they react preferentially, by adding 4mL of BF3 to 100mL of dry fractionally distilled 2,6-lutidine and redistilling. Distillation of commercial material from AlCl3 (14g per 100mL) can also be used to remove picolines (and water). Alternatively, lutidine (100mL) can be refluxed with ethyl benzenesulfonate (20g) or ethyl p-toluenesulfonate (20g) for 1hour, then the upper layer is cooled, separated and distilled. The distillate is refluxed with BaO or CaH2, then fractionally distilled through a glass helices-packed column. 2,6-Lutidine can be dried with KOH or sodium or by refluxing with (and distilling from) BaO, prior to distillation. For purification via its picrate, 2,6-lutidine, dissolved in absolute EtOH, is treated with an excess of warm ethanolic picric acid. The precipitate is filtered off, recrystallised from acetone (to give m 163-164.5o (166-167o), and partitioned between ammonia and CHCl3/diethyl ether. The organic layer, after washing with dilute aqueous KOH, is dried with Na2SO4 and fractionally distilled. [Warnhoff J Org Chem 27 4587 1962.] Alternatively, 2,6-lutidine can be purified via its urea complex, as described under 2,3-lutidine. Other purification procedures include azeotropic distillation with phenol [Coulson et al. J Appl Chem (London) 2 71 1952], fractional crystallisation by partial freezing, and vapour-phase chromatography using a 180-cm column of polyethylene glycol-400 (Shell, 5%) on Embacel (May and Baker) at 100o, with argon as carrier gas [Bamford & Block J Chem Soc 4989 1961]. The hydrochloride has m 235-237o, 239o (from EtOH). [Beilstein 20 II 160, 20 III/IV 2776, 20/6 V 32.]
6-METHYL-2-PYRIDINEPROPANOL, 98 3,5-DIMETHYLPYRIDINE-4-CARBOXALDEHYDE 2,6-DIMETHYL-3-HYDROXYPYRIDINE 2,4-Lutidine,1-ethyl-1,6-dihydro-6-imino-(8CI) 2,6-Lutidine,3-isopropyl-(6CI) 3,4-Lutidine,5-isopropyl-(6CI) 4-CHLORO-N,N-DIMETHYL-PYRIDINE-2-CARBOXAMIDE Tar bases, coal, lutidine fraction ,Tar bases, coal, lutidine fraction Distillate Bases 1,2,3,4,5,6,7,8-OCTAHYDROACRIDINE 2-BROMO-4,6-DIMETHYLPYRIDINE 2,5-LUTIDINE 98+%,2,5-DIMETHYLPYRIDINE, 2,5-LUTIDINE 2,6-lutidine-alpha(sup 2),3-diol,2,6-LUTIDINE-ALPHA-2,3-DIOL 99%,2,6-lutidine-α2,3-diol 4-Bromo-2,6-lutidine ETHYL 2,4-DIMETHYLPYRIDINE-3-CARBOXYLATE 3,4-Lutidine, 1-acetyl-1,2,5,6-tetrahydro- (7CI) 3,4-Lutidine,2,6-dimethoxy-(5CI) 2,3-LUTIDINE-N-OXIDE Lutidine-n-oxide

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