| Identification | More | [Name]
2,3-Lutidine | [CAS]
583-61-9 | [Synonyms]
2,3-DIMETHYLPYRIDINE
23L
2,3-LUTIDINE
LUT
2,3-dimethyl-pyridin
pyridine,2,3-dimethyl-
2,3-LUTIDINE/2,3-DIMETHYL PYRIDINE
2,3-LUTIDINE 98+%
2,3-Lutidine,99%
2,3-DIMETHYLPYRIDINE(2,3-LUTIDINE)
a,b-Dimethylpyridine | [EINECS(EC#)]
209-514-1 | [Molecular Formula]
C7H9N | [MDL Number]
MFCD00009605 | [Molecular Weight]
107.15 | [MOL File]
583-61-9.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to slightly yellow liquid | [Melting point ]
-15 °C (lit.) | [Boiling point ]
162-163 °C (lit.) | [density ]
0.945 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.508(lit.)
| [Fp ]
122 °F
| [storage temp. ]
Flammables area | [form ]
Liquid | [pka]
6.57(at 25℃) | [color ]
Clear colorless to slightly yellow | [Water Solubility ]
95 g/L (26 ºC) | [Specific Heat Capacity]
Cp(liquid):189.5J/(g·K),at 25℃ | [BRN ]
106418 | [Henry's Law Constant]
1.4×100 mol/(m3Pa) at 25℃, Andon et al. (1954) | [InChI]
1S/C7H9N/c1-6-4-3-5-8-7(6)2/h3-5H,1-2H3 | [InChIKey]
HPYNZHMRTTWQTB-UHFFFAOYSA-N | [SMILES]
CC1=C(N=CC=C1)C | [LogP]
1.638 (est) | [CAS DataBase Reference]
583-61-9(CAS DataBase Reference) | [NIST Chemistry Reference]
Pyridine, 2,3-dimethyl-(583-61-9) | [EPA Substance Registry System]
2,3-Dimethylpyridine (583-61-9) |
| Questions And Answer | Back Directory | [Synthesis]
The synthesis of 2,3-Lutidine, as described in the literature, starts with 2-bromo-3-methylpyridine. Under strongly basic conditions, bromine is removed to obtain the corresponding organolithium reagent, which is then added externally with iodomethane to yield the target product obtained by dehalogenation methylation of the pyridine ring. It is worth noting that this route uses flow synthesis chemistry. |
| Safety Data | Back Directory | [Symbol(GHS) ]
  
GHS02,GHS05,GHS07 | [Signal word ]
Danger | [Hazard statements ]
H226-H302-H315-H318-H335 | [Precautionary statements ]
P261-P280-P305+P351+P338 | [Hazard Codes ]
Xn,F,Xi | [Risk Statements ]
R10:Flammable.
R22:Harmful if swallowed.
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S39:Wear eye/face protection .
S36/37:Wear suitable protective clothing and gloves .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN 1993 3/PG 3
| [WGK Germany ]
3
| [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29333990 | [Storage Class]
3 - Flammable liquids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Dam. 1
Flam. Liq. 3
Skin Irrit. 2
STOT SE 3 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
2,3,4-trimethylpyridine-->Pyridine, 1,2,3,4-tetrahydro-5,6-dimethyl--->(2-Methylpyridin-3-yl)methyl acetate-->Ethanone, 1-(1-methyl-3-piperidinyl)- (9CI)-->2,3,6-Trimethylpyridine-->(2-Methyl-pyridin-3-yl)-methanol-->3-Ethylpyridine-->Ethyl 2-methylnicotinate | [Preparation Products]
2-Chloromethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine hydrochloride-->3-Methyl-2-pyridinecarboxaldehyde-->2-Hydroxymethyl-3-methylpyridine-->2,3-Dimethyl-pyridin-4-ylamine-->2-Chloromethyl-3-methyl-4-(3-methoxypropoxy)pyridine hydrochloride-->4-Chloro-2,3-dimethylpyridine 1-oxide-->Lansoprazole-->2-Hydroxymethyl-4-methoxypropoxy-3-methylpyridine-->4-Nitro-2,3-lutidine-N-oxide-->2,3-Dimethylpyridine-N-oxide-->2,6-Lutidine-->Pyridine |
| Hazard Information | Back Directory | [Description]
2,3-Lutidine(583-61-9) belongs to the pyridine group of derivatives and is a commercially available organic reagent used as an intermediate in organic synthesis and as an acid-binding agent. It is also used as a food additive for flavouring purposes.
| [Chemical Properties]
clear colorless to slightly yellow liquid | [Uses]
2,3-Lutidine(583-61-9) is a lansoprazole intermediates. It is used as pharmaceutical intermediate.
| [Definition]
LOTUS: 2,3-Lutidine is a natural product found in Nicotiana tabacum with data available. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 66, p. 53, 2001 DOI: 10.1021/jo000724t | [Purification Methods]
Steam distil it from a solution containing about 1.2 equivalents of 20% H2SO4, until ca 10% of the base has been carried over with the non-basic impurities. The acidic solution is then made alkaline, and the base is separated, dried over NaOH or BaO, and fractionally distilled. The distilled lutidine is converted to its urea complex by stirring 100g with 40g of urea in 75mL of H2O, cooling to 5o, filtering at the pump, and washing with 75mL of H2O. The complex, dissolved in 300mL of H2O, is steam distilled until the distillate gives no turbidity with a little solid NaOH. The distillate is then treated with excess solid NaOH, and the upper layer is removed: the aqueous layer is then extracted with diethyl ether. The upper layer and the ether extract are combined, dried (K2CO3), and distilled through a short column. Final purification is by fractional crystallisation using partial freezing. The picrate crystallises from EtOH with m 187-188o. [Kyte et al. J Chem Soc 4454 1960, Beilstein 20 H 243, 20 II 159, 20 III/IV 2765, 20/6 V 15.] |
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