108-47-4 Usage
Description
2,4-Lutidine, also known as 2,4-dimethylaniline or N-(2-methylphenyl)methanamine, is an organic compound belonging to the aromatic amine class. It is a clear pale yellow liquid that tends to discolor over time and has a high strength odor, with aroma threshold values recommending smelling in a 0.01% solution or less. The compound is characterized by the presence of a nitrogen atom bonded to a methyl group and a phenyl ring, which contributes to its unique chemical properties and potential applications.
Uses
Used in Chemical Synthesis:
2,4-Lutidine is used as a reagent in the chemical synthesis industry for various organic compounds. Its ability to act as a nucleophile and participate in reactions such as substitution, addition, and condensation makes it a versatile building block for creating a wide range of chemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,4-Lutidine is used as an intermediate in the synthesis of various drugs and pharmaceutical compounds. Its unique chemical structure allows it to be incorporated into the development of new medications, potentially leading to improved therapeutic options for various medical conditions.
Used in Dyes and Pigments:
2,4-Lutidine is used as a chemical intermediate in the production of dyes and pigments. Its aromatic structure and reactivity make it suitable for the creation of a variety of colorants used in the textile, paint, and plastics industries.
Used in Laboratory Research:
Due to its unique chemical properties, 2,4-Lutidine is used as a research compound in various scientific studies. It can be employed in the investigation of chemical reactions, the development of new synthetic methods, and the exploration of its potential applications in various fields.
Used in Corrosion Inhibition:
2,4-Lutidine is used as a corrosion inhibitor in the oil and gas industry. Its ability to form complexes with metal surfaces helps protect pipelines and other equipment from corrosion, extending their lifespan and reducing maintenance costs.
Used in Rubber Industry:
In the rubber industry, 2,4-Lutidine is used as an accelerator in the vulcanization process. It helps to speed up the formation of cross-links between rubber molecules, improving the rubber's strength, elasticity, and durability.
Used in Agrochemicals:
2,4-Lutidine is used as an intermediate in the synthesis of various agrochemicals, such as pesticides and herbicides. Its unique chemical properties make it a valuable component in the development of new and effective products for agricultural applications.
Purification Methods
Dry it with Linde type 5A molecular sieves, BaO or sodium, and fractionally distil it. The distillate (200g) is heated with *benzene (500mL) and conc HCl (150mL) in a Dean and Stark apparatus on a water bath until water no longer separates, and the temperature just below the liquid reaches 80o. When cold, the supernatant *benzene is decanted, and the 2,4-lutidine hydrochloride, after washing with a little *benzene, is dissolved in water (350mL). After removing any *benzene by steam distillation, an aqueous solution of NaOH (80g) is added, and the free lutidine is steam distilled. It is isolated by saturating the distillate with solid NaOH and distilling it through a short column. The precipitation cycle is repeated, then the final distillate is partly frozen in an apparatus at -67.8-68.5o (cooled by acetone/CO2). The crystals are collected, then melted and distilled. [Kyte et al. J Chem Soc 4454 1960.] Alternative purifications are via the picrate m 183-184o (from H2O). [Clarke & Rothwell J Chem Soc 1885 1960], or the hydrobromide [Warnhoff J Org Chem 27 4587 1962]. The latter is precipitated from a solution of lutidine in *benzene by passing dry HBr gas: the salt is recrystallised from CHCl3/methyl ethyl ketone, then decomposed with NaOH, and the free base is extracted into Et2O, dried, evaporated and the residue is distilled. [Beilstein 20 H 244, 20 II 180, 20 III/IV 2718, 20/6 V 19.]
Check Digit Verification of cas no
The CAS Registry Mumber 108-47-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 8 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 108-47:
(5*1)+(4*0)+(3*8)+(2*4)+(1*7)=44
44 % 10 = 4
So 108-47-4 is a valid CAS Registry Number.
108-47-4Relevant articles and documents
Flow synthesis of 2-methylpyridines via α-methylation
Manansala, Camille,Tranmer, Geoffrey K.
, p. 15797 - 15806 (2015)
A series of simple 2-methylpyridines were synthesized in an expedited and convenient manner using a simplified bench-top continuous flow setup. The reactions proceeded with a high degree of selectivity, producing α-methylated pyridines in a much greener fashion than is possible using conventional batch reaction protocols. Eight 2-methylated pyridines were produced by progressing starting material through a column packed with Raney nickel using a low boiling point alcohol (1-propanol) at high temperature. Simple collection and removal of the solvent gave products in very good yields that were suitable for further use without additional work-up or purification. Overall, this continuous flow method represents a synthetically useful protocol that is superior to batch processes in terms of shorter reaction times, increased safety, avoidance of work-up procedures, and reduced waste. A brief discussion of the possible mechanism(s) of the reaction is also presented which involves heterogeneous catalysis and/or a Ladenberg rearrangement, with the proposed methyl source as C1 of the primary alcohol.
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Myerly,Weinberg
, p. 2008 (1966)
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Bimetallic C-C Bond-Forming Reductive Elimination from Nickel
Xu, Hongwei,Diccianni, Justin B.,Katigbak, Joseph,Hu, Chunhua,Zhang, Yingkai,Diao, Tianning
, p. 4779 - 4786 (2016)
Ni-catalyzed cross-coupling reactions have found important applications in organic synthesis. The fundamental characterization of the key steps in cross-coupling reactions, including C-C bond-forming reductive elimination, represents a significant challenge. Bimolecular pathways were invoked in early proposals, but the experimental evidence was limited. We present the preparation of well-defined (pyridine-pyrrolyl)Ni monomethyl and monophenyl complexes that allow the direct observation of bimolecular reductive elimination to generate ethane and biphenyl, respectively. The sp3-sp3 and sp2-sp2 couplings proceed via two distinct pathways. Oxidants promote the fast formation of Ni(III) from (pyridine-pyrrolyl)Ni-methyl, which dimerizes to afford a bimetallic Ni(III) intermediate. Our data are most consistent with the subsequent methyl coupling from the bimetallic Ni(III) to generate ethane as the rate-determining step. In contrast, the formation of biphenyl is facilitated by the coordination of a bidentate donor ligand.
Transformations of pyridine bases on a nickel-aluminum catalyst
Antonova,Ovchinnikova,Bespalov,Serova,Promonenkov,Ustavshchikov
, p. 280 - 283 (1982)
The electronic structures of some pyridine bases are analyzed by means of 1H and 13C NMR spectroscopic data for substituted pyridines and the calculated bond orders in the pyridine ring. The differences in the chemical bonds in the pyridine ring of isomeric methylpyridines and the carbon-carbon bonds between the ring and the methyl groups in these compounds are in agreement with the experimental data on the thermal stability of the simplest pyridine bases and the gas-phase transformation of the isomeric methylpyridines on an industrial nickel-aluminum catalyst. The possibility of obtaining mono- or dialkylpyridines under these conditions, depending on the structure of the starting pyridine bases, is demonstrated.
A mild and efficient H2O2 oxygenation of N-heteroaromatic compounds to the amine N-oxides and KI deoxygenation back to the tertiary amine with hexaphenyloxodiphosphonium triflate
Khodaei, Mohammad Mehdi,Alizadeh, Abdolhamid,Hezarkhani, Hadis Afshar
, p. 1843 - 1849 (2018/07/06)
A mild and efficient method for the oxidation of N-heteroaromatic compounds to the corresponding N-oxides using H2O2 in the presence of hexaphenyloxodiphosphnium triflate (Hendrickson reagent) in EtOH at room temperature was reported. This methodology presented relatively fast and selective reactions to afford the N-oxides in good yields. The reverse reactions, deoxygenation reactions, were also carried out under the same reaction conditions by KI to produce the tertiary amines.