ChemicalBook CAS DataBase List 108-48-5

108-48-5

Name	2,6-Lutidine
CAS	108-48-5
EINECS(EC#)	203-587-3
Molecular Formula	C7H9N
MDL Number	MFCD00006345
Molecular Weight	107.15
MOL File	108-48-5.mol

Synonyms

2,6-DIMETHYLPYRIDINE 26L 2,6-LUTIDINE DIMETHYLPYRIDINE(2,6-) FEMA 3540 FEMA NUMBER 3540 2,6-dimethyl-pyridin 2,6-Dimethypyridine 2,6-Lutidene alpha,alpha’-dimethylpyridine alpha,alpha’-lutidin alpha,alpha’-lutidine alpha,alpha'-Dimethylpyridine alpha,alpha'-Lutidin alpha,alpha'-Lutidine Pyridine,2,6-dimethyl- 2,6-Lutidine 2,6-Dimethylpyridine 2 6-DIMETHYLPYRIDINE 99+% 2,6-LUTIDINE, REDISTILLED, 99+% 2 6-LUTIDINE REAGENTPLUS(TM) 99%

Chemical Properties

Appearance	Colorless to yellow liquid
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
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
Stability:	Stable. Flammable. Incompatible with strong oxidizing agents, acid chlorides, acids, chloroformates. Protect from moisture.
biological source	synthetic
Odor Type	nutty
Water Solubility	40 g/100 mL (20 ºC)
Specific Heat Capacity	Cp(liquid):185.2J/(g·K),at 25℃
Sensitive	Hygroscopic
Detection Methods	GC,NMR
JECFA Number	1317
Merck	14,5616
BRN	105690
Henry's Law Constant	9.2×10^-1 mol/(m³Pa) at 25℃, Brockbank (2013)
Dielectric constant	7.3300000000000001
Major Application	flavors and fragrances
InChI	1S/C7H9N/c1-6-4-3-5-7(2)8-6/h3-5H,1-2H3
InChIKey	OISVCGZHLKNMSJ-UHFFFAOYSA-N
SMILES	Cc1cccc(C)n1
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	108-48-5(EPA Substance)

Safety Data

Symbol(GHS)	GHS02,GHS07
Signal word	Warning
Hazard statements	H226-H302-H315-H319
Precautionary statements	P210-P301+P312+P330-P302+P352-P305+P351+P338
Hazard Codes	Xn,F,Xi
Risk Statements	R10:Flammable. R22:Harmful if swallowed. R36/37/38:Irritating to eyes, respiratory system and skin . R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . less more
Safety Statements	S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36/37:Wear suitable protective clothing and gloves . S16:Keep away from sources of ignition-No smoking . S36:Wear suitable protective clothing . S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . less more
RIDADR	UN 1993 3/PG 3
WGK Germany	3
RTECS	OK9700000
F	8
Hazard Note	Irritant/Flammable
TSCA	Yes
REACH Registrations	Active
HazardClass	3
PackingGroup	III
HS Code	29333999
Storage Class	3 - Flammable liquids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Flam. Liq. 3 Skin Irrit. 2
Hazardous Substances Data	108-48-5(Hazardous Substances Data)
Toxicity	LD50 orally in Rabbit: 400 mg/kg LD50 dermal Rabbit > 1000 mg/kg less more

Raw materials And Preparation Products

Hazard Information

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.

Reactivity Profile

LUTIDENE(108-48-5) 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.

Air & Water Reactions

Highly flammable. Soluble in water.

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.

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.

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

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.]

Material Safety Data Sheet(MSDS)

Questions And Answer

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;
Acute toxicity
oral – rat LD50: 400mg/kg;
Toxicity grade
high toxic;
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.;

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108-48-5

Chemical Properties

Safety Data

Raw materials And Preparation Products

Raw materials

Preparation Products

Hazard Information

General Description

Reactivity Profile

Air & Water Reactions

Health Hazard

Occurrence

Uses

Definition

Taste threshold values

Synthesis Reference(s)

Flammability and Explosibility

Synthesis

Purification Methods

Material Safety Data Sheet(MSDS)

Questions And Answer

Chemical Properties

Usage

Preparation

Category

Acute toxicity

Toxicity grade

Flammability hazard characteristics

Storage

Fire extinguishing agents

Spectrum Detail

Well-known Reagent Company Product Information

Supplier

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