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| | 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 | | pka | 6.65(at 25℃) | | color | Clear | | Odor | at 1.00 % in dipropylene glycol. nutty amine woody bready cocoa oily | | Odor Type | nutty | | Water Solubility | 40 g/100 mL (20 ºC) | | Sensitive | Hygroscopic | | Merck | 14,5616 | | JECFA Number | 1317 | | BRN | 105690 | | Stability: | Stable. Flammable. Incompatible with strong oxidizing agents, acid chlorides, acids, chloroformates. Protect from moisture. | | LogP | 0.12 at 25℃ | | CAS DataBase Reference | 108-48-5(CAS DataBase Reference) | | NIST Chemistry Reference | Pyridine, 2,6-dimethyl-(108-48-5) | | EPA Substance Registry System | 2,6-Dimethylpyridine (108-48-5) |
| | 2,6-Lutidine Usage And Synthesis |
| Chemical Properties | Colorless 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. | | Usage | 2,6-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. | | Preparation | 2,6-Lutidine is obtained through the separation of β-methylpyridine which is a recycled product of coal coking byproduct. | | Category | flammable liquid | | Toxicity grade | high toxic | | Acute toxicity | oral – rat LD50: 400mg/kg | | Flammability hazard characteristics | flammable in case of fire, high temperature and oxidant, releasing toxic nitrogen oxides in case of heat. | | Storage | Ventilated and dry warehouse with low temperature, separated from acids. | | Fire extinguishing agents | Dry powder, dry sand, carbon dioxide, foam. | | Chemical Properties | 2,6-Dimethylpyridine has a powerful and diffusive minty-tarry odor. It has also been described to have the odor of
pyridine and peppermint | | Chemical Properties | Colorless to yellow liquid | | Occurrence | Reported found in bread, tea, peppermint oil, cheeses, chicken, beef, pork, beer, sherry, whiskies, cocoa, coffee, tea, oatmeal, rice bran, buckwheat and malt. | | Uses | Isolated from the basic fraction of coal tar. A semi-volatile compound in tobacco. | | Uses | 2,6-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. | | Definition | ChEBI: A member of the class of methylpyridines that is pyridine carrying methyl substituents at positions 2 and 6. | | Taste threshold values | Taste 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 Description | A 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 Reactions | Highly flammable. Soluble in water. | | Reactivity Profile | 2,6-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 Hazard | Inhalation 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 Explosibility | Flammable | | Synthesis | Synthesis from ethyl acetoacetate, formaldehyde and ammonia; isolated from basic fraction of coal tar | | Purification Methods | Likely 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.] |
| | 2,6-Lutidine Preparation Products And Raw materials |
| Raw materials | Ethanol-->Diethyl ether-->Sulfuric acid-->Nitric acid-->Potassium hydroxide-->Ammonium hydroxide-->Ammonia-->Formaldehyde-->Ethyl acetoacetate-->Calcium chloride-->Diethylamine-->Calcium oxide-->3-Picoline | | Preparation Products | Bergapten-->5-bromo-1,2,3,4-tetrahydroisoquinoline-->2,6-DIMETHYL-PYRIDIN-4-YLAMINE-->7-BROMO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-->Pyridine-2,6-dicarboxylic acid-->2,4-Lutidine-->2-(HYDROXYETHYL)-6-METHYLPYRIDINE-->Cefpiramide acid-->2-(Bromomethyl)-6-methylpyridine-->2,6-Pyridinedimethanol-->6-BROMOMETHYL-2-PYRIDINECARBOXYLIC ACID-->2,6-Dimethylpyridine N-oxide-->3-AMINO-2,6-DIMETHYLPYRIDINE-->3-Bromo-2,6-dimethylpyridine-->6-Methyl-2-pyridinecarboxylic acid-->2,6-Dimethyl-3-nitropyridine-->2,6-BIS(CHLOROMETHYL)PYRIDINE-->2-METHYL-6-VINYLPYRIDINE-->(2S,6S)-2,6-dimethylpiperidine |
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