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Cas Database

108-89-4

108-89-4

Identification

  • Product Name:Pyridine, 4-methyl-

  • CAS Number: 108-89-4

  • EINECS:203-626-4

  • Molecular Weight:93.1283

  • Molecular Formula: C6H7N

  • HS Code:29333955

  • Mol File:108-89-4.mol

Synonyms:4-Picoline(8CI);Ba 35846;NSC 18252;p-Methylpyridine;p-Picoline;g-Methylpyridine;g-Picoline;

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Safety information and MSDS view more

  • Pictogram(s):ToxicT

  • Hazard Codes:T

  • Signal Word:Danger

  • Hazard Statement:H226 Flammable liquid and vapourH302 Harmful if swallowed H311 Toxic in contact with skin H315 Causes skin irritation H319 Causes serious eye irritation H332 Harmful if inhaled H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Do NOT induce vomiting. Rest. Refer for medical attention . ACUTE/CHRONIC HAZARDS: Moderate fire risk. /SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aromatic hydrocarbons and related compounds/

  • Fire-fighting measures: Suitable extinguishing media To fight fire, use alcohol foam. Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. (ERG, 2016) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Personal protection: chemical protection suit including self-contained breathing apparatus. Accidental Release Measures. Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Fireproof. Separated from strong oxidants. Well closed.Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:4-Methylpyridine
  • Packaging:50g
  • Price:$ 195
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  • Manufacture/Brand:TCI Chemical
  • Product Description:4-Methylpyridine >98.0%(GC)(T)
  • Packaging:25mL
  • Price:$ 15
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  • Manufacture/Brand:TCI Chemical
  • Product Description:4-Methylpyridine >98.0%(GC)(T)
  • Packaging:500mL
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:4-Methylpyridine
  • Packaging:25 g
  • Price:$ 27
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:4-Methylpyridine
  • Packaging:100 g
  • Price:$ 45
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:4-Picoline analytical standard
  • Packaging:5ml
  • Price:$ 249
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:4-Picoline analytical standard
  • Packaging:1ml
  • Price:$ 62.7
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:4-Methylpyridine for synthesis. CAS 108-89-4, molar mass 93.13 g/mol., for synthesis
  • Packaging:8070490010
  • Price:$ 19
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:4-Methylpyridine for synthesis
  • Packaging:10 mL
  • Price:$ 18.22
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:4-Methylpyridine for synthesis. CAS 108-89-4, molar mass 93.13 g/mol., for synthesis
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Relevant articles and documentsAll total 144 Articles be found

Structural Effects on the Iodine Cation Basicity of Organic Bases in the Gas Phase

Abboud, Jose-Luis M.,Notario, Rafael,Santos, Lucia,Lopez-Mardomingo, Carmen

, p. 8960 - 8961 (1989)

-

Coombes, R. G.,Johnson, M. D.,Tobe, M. L.,Winterton, N.,Wong, L. Y.

, (1965)

SITE OF PROTONATION AND CONFORMATIONAL EFFECTS ON GAS-PHASE BASICITY IN beta -AMINO ALCOHOLS. THE NATURE OF INTERNAL H BONDING IN beta -HYDROXY AMMONIUM IONS.

Houriet,Reufenacht,Carrupt,Vogel,Tichy

, p. 3417 - 3422 (1983)

The influence of interfunctional distance on the gas-phase basicity of beta -amino alcohols is investigated by the method of equilibrium proton-transfer reactions in an ion cyclotron resonance (ICR) spectrometer. It is found that in the protonated species, interaction between the most basic center (amino group) with the hydroxy group results in stabilization of the system. The stabilization energy increases as the interfunctional distance decreases to reach a maximum value of about 7 kcal/mol for coplanar systems. Comparison with the values determined by ab initio calculations indicates that internal H bonding can be described in terms of the ion-dipole potential energy between the ammonium ion and the hydroxy group. External vs. internal ion solvation effects are also discussed.

Synthesis, spectral, thermal and kinetic studies on the adducts with pyridines of tungsten(V) binuclear thiocomplexes with di-isopropyl-dithiocarbamate

Lozano,de Jesús,Lozano

, p. 3127 - 3132 (2006)

We report the synthesis and the thermal and kinetic behaviour of di-μ-sulfido-bis-(sulfido N,N,di-i-propyldithiocarbamate)di-tungsten(V) adducts with pyridine or substituted pyridines, the formula of which is [W2S4(di-i-propyldtc)2B2], where dtc = dithiocarbamate and B = pyridine (Py), 3-methylpyridine (3-MP), 4-methylpyridine (4-MP), 3,5-dimethylpyridine (3,5-DMP), 3-aminopyridine (3-AP) and 4-aminopyridine (4-AP). The synthesized complexes have been identified by IR and electronic spectra, magnetic susceptibility measurements and analytical data. We have also inferred the thermal behaviour and kinetic parameters by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) of the thermal decomposition of these adducts in the solid state. From the DSC curves, the activation energies and pre-exponential Arrhenius factors for the endothermic process corresponding to the loss of two moles of coordinated base were calculated. We have also deduced the reaction mechanism using a new non-isothermal kinetic method. Steric hindrance and inductive effects prompted by amino and methyl pyridine functional groups in the adducts formation are discussed. A relationship between the pyridines basicity, infrared and electronic spectral data and activation energies has also been explored.

Two-State Reactivity in Iron-Catalyzed Alkene Isomerization Confers σ-Base Resistance

Lutz, Sean A.,Hickey, Anne K.,Gao, Yafei,Chen, Chun-Hsing,Smith, Jeremy M.

, p. 15527 - 15535 (2020)

A low-coordinate, high spin (S = 3/2) organometallic iron(I) complex is a catalyst for the isomerization of alkenes. A combination of experimental and computational mechanistic studies supports a mechanism in which alkene isomerization occurs by the allyl mechanism. Importantly, while substrate binding occurs on the S = 3/2 surface, oxidative addition to an η1-allyl intermediate only occurs on the S = 1/2 surface. Since this spin state change is only possible when the alkene substrate is bound, the catalyst has high immunity to typical σ-base poisons due to the antibonding interactions of the high spin state.

Pd0-mediated rapid coupling between methyl iodide and heteroarylstannanes: an efficient and general method for the incorporation of a positron-emitting11C radionuclide into heteroaromatic frameworks

Suzuki, Masaaki,Sumi, Kengo,Koyama, Hiroko,Siqin,Hosoya, Takamitsu,Takashima-Hirano, Misato,Doi, Hisashi

, p. 12489 - 12495 (2009)

The Pd0-mediated rapid trapping of methyl iodide with an excess amount of a heteroaryl-substituted tributylstannane has been investigated with the aim of incorporating a shortlived 11C-labelled methyl group into the heteroaromatic carbon frameworks of important organic compounds, such as drugs with various heteroaromatic structures, in order to execute a positron emission tomography (PET) study of vital systems. The reaction was first performed by using our previously developed CH3I/stannane/[Pd 2(dba)3]/ P(o-CH3C6H 4)3/CuCl/K2CO3 (1:40:0.5:2:2:2) system in DMF at 60°C for 5 min (conditions A), however, the reaction gave low yields for various heteroaromatic compounds. Increasing the amount of phosphine ligand (condi tions B) led to a significant improvement in the yield, but the conditions were still not suitable for a range of basic heteroaromatic structures. Use of the CuBr/CsF system (conditions C) also provided a result similar to that obtained under conditions B with an increased amount of the phosphine. Thus, pyridine and related heteroaromatic compounds remained less reactive substrates. The problem was overcome by replacing the DMF solvent with N-methyl-2-pyrolidinone (NMP). The reaction in NMP at 60-100°C for 5 min using a CH3I/stannane/[Pd2-(dba)3]/P(o-CH 3C6H4)3/CuBr/CsF (1:40:0.5:16:2:5) combination (conditions D) gave the methylated products in yields of more than 80% (based on the reaction of CH3I) for all of the heteroaromatic compounds listed in this study. Thus, the combined use of NMP and an increased amount of phosphine is important for promoting the reaction efficiently. The use of this general approach to rapid methylation has been well demonstrated by the synthesis of the PET tracers 2- and 3-[11C]methylpyridines by using [Pd2(dba)3]/P(o-CH3C6H 4)3/CuBr/CsF (1:16:2:5) in NMP at 60°C for 5 min, which gives the desired products in HPLC analytical yields of 88 and 91%, respectively.

Oxygenation of hydrocarbons mediated by mixed-valent basic iron trifluoroacetate and valence-separated component species under Gif-type conditions involves carbon- and oxygen-centered radicals

Tapper, Amy E.,Long, Jeffrey R.,Staples, Richard J.,Stavropoulos, Pericles

, p. 2343 - 2346 (2000)

Hydrogen-atom abstraction by hydroxyl radicals takes place to generate both tert- and sec-adamantyl radicals in Gif-type oxygenation of adamantane by H2O2 in pyridine/trifluoroacetic acid when the reaction is mediated by [Fe(O2CCF3)2(py)4] or [Fe2O(O2CCF3)4(py)6], which are formed by dissociation of [Fe3O(O2CCF3)6- (L)3] in pyridine (L = H2O, DMSO; see scheme).

-

Tschitschibabin

, p. 1623 (1937)

-

Lozano, Rafael,Roman, Jesus,De Jesus, Fernando,Alarcon, Esteban

, p. 231 - 238 (1991)

Unsaturated aldehydes: a novel route for the synthesis of pyridine and 3-picoline

Luo, Cai-Wu,Chao, Zi-Sheng

, p. 54090 - 54101 (2015)

A novel reaction pathway was developed for the synthesis of pyridine and 3-picoline from the condensation of gas-phase acrolein dimethyl acetal or acrolein diethyl acetal and ammonia over various catalysts in a fixed-bed reactor. ZnO loaded on alkaline-acid sequentially-treated HZSM-5, namely ZnO/HZSM-5-At-acid, was prepared and employed in these reactions for the first time. 3-Picoline, without the generation of 4-picoline, was obtained from the condensation of acrolein dimethyl acetal and ammonia. The ZnO/HZSM-5-At-acid catalyst was proven to be the most promising catalyst relative to other catalysts in this study. The stability of the ZnO/HZSM-5-At-acid catalyst was remarkably higher than that of the ZnO/HZSM-5 catalyst. The catalysts were characterized using XRD, 27Al MAS NMR, XPS, UV-vis DRS, N2-physisorption, NH3-TPD and TG technologies and the results revealed that the pore structure, acidity and location of ZnO had great influence on the total yield of pyridine and 3-picoline, and the catalyst stability.

A computational, X-ray crystallographic and thermal stability analysis of TETROL and its pyridine and methylpyridine inclusion complexes

Barton, Benita,Caira, Mino R.,Hosten, Eric C.,McCleland, Cedric W.

, p. 8713 - 8723 (2013)

The identification and application of (+)-(2R,3R)-1,1,4,4- tetraphenylbutane-1,2,3,4-tetrol (TETROL) as an efficient and selective host compound is described. Computational and single crystal X-ray diffraction analyses revealed that the butane backbone of TETROL adopts a relatively rigid anti-conformation, with the hydroxy groups oriented syn and connected through a cyclic, homodromic arrangement of their O-H bonds. This structure is stabilised through a pair of 1,3-hydrogen bonding interactions. TETROL forms inclusion complexes with pyridine and 3- and 4-methylpyridine, and does so selectively from mixtures of the pyridines. X-ray diffraction (single crystal and powder) and thermal analyses of the inclusion compounds are described.

Thermal study of [Pd(2-Phpy)Cl(L)] complexes (L=pyridines and amines)

Perez,Sanchez,Garcia,Serrano,Lopez

, p. 361 - 370 (2001)

The complex [Pd(2-Phpy)(μ-Cl)]2 reacts with pyridines (L=pyridine, α-picoline and γ-picoline), amines (L=isopropylamine, tert-butylamine) and ammonia to form the corresponding ortho-palladated derivatives [Pd(2-Phpy)CIL]. The compounds have bee

Nitrogen kinetic isotope effects on the decarboxylation of 4-pyridylacetic acid

Sicinska,Lewandowicz,Vokal,Paneth

, p. 5534 - 5536 (2001)

Nitrogen kinetic isotope effects on the decarboxylation of 4-pyridylacetic acid have been measured in solvents of different polarity and have been found to vary from the inverse value of 0.994 to the normal value of 1.002 upon increase of water content of

Coombes,Johnson

, p. 177 (1966)

Kinetics and mechanistic study on deoxygenation of pyridine oxide catalyzed by {MeReVO(pdt)} 2 dimer

Ibdah, Abdellatif,Alduwikat, Salwa

, p. 9 - 20 (2017)

The oxorhenium(V) dimer {MeReO(pdt)}2 (where pdt?=?1,2-propanedithiolate) catalyze the oxygen atom transfer (OAT) reaction from the pyridine oxide to triphenylarsine (Ph3As). The rate law is given by ν?=?k[Re-dimer][PyNO] and zero order dependence on Ph3As. The value of k at 25?°C in CHCl3 is 139?±?3?L?mol?1?s?1. The activation parameters are ΔH??=?12.2?±?1.0?kcal?mol?1 and ΔS??=??7.9?±?3.24?cal?K?1?mol?1. According to the proposed mechanism, the rate determining step is the oxidation of ReVO to ReVIIO2 and the pyridine release. The triphenylarsine enters the catalytic cycle after the rate determining step. The reaction constant ρ?=??1.4 obtained from Hammett correlation with σ for different substituted pyridine N-oxide. The computational study indicates that the oxidation of ReV to ReVII and release of the pyridine step is insensitive to the nature of the substituent on the pyridine with the average estimated activation barrier ≈11.5?kcal/mol from six different substituted pyridine oxide. It is proposed that electron donor substituent enrich the equilibrium of the first step of the proposed mechanism which is the coordination of the pyridine oxide with one rhenium atom to form I1 (Scheme 2). The electron donor substituent on the pyridine increase the concentration of I1 which will increase the rate of the reaction as the ν?=?k2[I1].

Properties of mixed polyfunctional fluoride catalysts for synthesis of pyridine bases from acetylene and ammonia (methanol)

Khamidullaev,Yusupov

, p. 939 - 942 (2003)

New catalysts based on cadmium, zinc, chromium, iron, and aluminum compounds were synthesized and their properties were studied. A pilot catalyst batch was obtained and tested on a pilot installation.

SYNTHESIS OF METHYLPYRIDINES IN THE PRESENCE OF Pd COMPLEXES CONTAINING S

Chekurovskaya, E. D.,Akimov, A. N.,Vaistub, T. G.,Tarasova, T. M.

, p. 1070 - 1072 (1991)

Synthesis of methylpyridines from acetaldehyde and ammonia in the presence of heterogeneous Pd complexes containing S is studied by a pulsed microcatalytic method.The process occurs with selective formation of 4-methylpyridine.The difference in the catalytic activity of the studied complexes is explained on the basis of 13C NMR spectra.

NMR Studies of Picolyl-type Carbanions. VIII. Anions Produced by Reactions of Alkyl-substituted Pyridines with Butyllithium

Konishi, Kazuyori,Matsumoto, Hiroshi,Saito, Katsuhiro,Takahashi, Kensuke

, p. 2294 - 2297 (1985)

The 1H and 13C NMR spectra have been observed for the anions, produced from methyl-, ethyl-, and isopropylpyridines, in tetrahydrofuran (THF).Two kinds of anions are formed concomitantly by lithium-proton exchange and addition of butyllithium from 2-ethyl, 2-isopropyl, 4-methyl, and 4-ethylpyridines.The former reaction tends to occur at the substituent bonded to the position adjacent to nitrogen, and the latter one occurs at the position adjacent to nitrogen without substituent.In the anions formed by the exchange from 2- and 4-ethylpyridines, a specific ring protonis coupled to the α-carbon, and, further, the ortho- or meta-protons (or -carbons) in the latter anion are nonequivalent respectively at room temperature.The α-carbons in these anions are virtually sp2-hybridized.

Polycyclic N-hetero compounds. XIII. Reactions of pyridine N-oxides with formamide

Koyama,Nanba,Hirota,et al.

, p. 964 - 967 (1977)

-

Nucleophilicities and carbon basicities of pyridines

Brotzel, Frank,Kempf, Bernhard,Singer, Thomas,Zipse, Hendrik,Mayr, Herbert

, p. 336 - 345 (2007)

Rate and equilibrium constants for the reactions of pyridines with donor-substituted benzhydrylium ions have been determined spectrophotometrically. The correlation equation log k(20°C) = s(N+E). in which s and N are nucleophile-specific parameters and E is an electrophile-specific parameter, has been used to determine the nucleophilicity parameters of various pyridines in CH2Cl2 and aqueous solution and to compare them with N of other nucleophiles. It is found that the nucleophilic organocatalyst 4-(dimethylamino)pyridine (DMAP) and tertiary phosphanes have comparable nucleophilicities and carbon basicities despite widely differing Bronsted basicities. For that reason, these reactivity parameters are suggested as guidelines for the development of novel organocatalysts. The Marcus equation is employed for the determination of the intrinsic barriers of these reactions.

Kinetic and Computational Studies of Rhenium Catalysis for Oxygen Atom Transfer Reactions

Ibdah, Abdellatif,Bakar, Heba Bani,Alduwikat, Salwa

, p. 149 - 159 (2018)

The rhenium(v)oxo dimer {MeReO(edt)}2 (edt≤1,2-ethanedithiolate) is an effective catalyst for the oxygen atom transfer (OAT) reaction from pyridine oxide and picoline oxide to triphenylarsine (Ph3As) as oxygen acceptor. Kinetics measurements were carried

Lozano, R.,Roman, J.,Jesus, F. de,Pena, J. L. de la

, p. 125 - 130 (1990)

Expansion of Azulenes as Nonbenzenoid Aromatic Compounds for C-H Activation: Rhodium- And Iridium-Catalyzed Oxidative Cyclization of Azulene Carboxylic Acids with Alkynes for the Synthesis of Azulenolactones and Benzoazulenes

Maeng, Chanyoung,Son, Jeong-Yu,Lee, Seung Cheol,Baek, Yonghyeon,Um, Kyusik,Han, Sang Hoon,Ko, Gi Hoon,Han, Gi Uk,Lee, Kyungsup,Lee, Kooyeon,Lee, Phil Ho

, p. 3824 - 3837 (2020)

Rhodium-catalyzed oxidative [4 + 2] cyclization reactions through the C-H activation of azulene carboxylic acids as nonbenzenoid aromatic compounds with symmetrical and unsymmetrical alkynes were developed under aerobic conditions, which produced azulenolactone derivatives with a wide substrate scope and excellent functional group tolerance. Interestingly, azulenic acids in reaction with alkynes underwent iridium-catalyzed [2 + 2 + 2] cyclization accompanied by decarboxylation to afford tetra(aryl)-substituted benzoazulene derivatives. The reactivity order for C-H activation reaction is greater toward azulene-6-carboxylic acid, azulene-1-carboxylic acid, and azulene-2-carboxylic acid. For the first time, the expansion of azulenes having directing group as nonbenzenoid aromatic compounds for C-H activation was successful, indicating that nonbenzenoid aromatic compounds can be used as good substrates for the C-H activation reaction. Therefore, the research area of C-H activation will certainly expand to nonbenzenoid aromatic compounds in future.

Can Heteroarenes/Arenes Be Hydrogenated Over Catalytic Pd/C Under Ambient Conditions?

Tanaka, Nao,Usuki, Toyonobu

, p. 5514 - 5522 (2020)

Hydrogenation of over a dozen aromatic compounds, including both heteroarenes and arenes, over palladium on carbon (Pd/C, 1–100 molpercent) with H2-balloon pressure at room temperature is reported. Analyses using pyridine as a model substrate revealed that acetic acid was the best solvent, as using only 1 molpercent Pd/C provided piperidine quantitatively. Substrate scope analysis and density functional theory calculations indicated that reaction rates are highly dependent on frontier molecular orbital characteristics and the steric bulkiness of substituents. Moreover, the established method was used for the concise synthesis of the anti-Alzheimer drug donepezil (Aricept?).

Nonclassical oxygen atom transfer reactions of oxomolybdenum(vi) bis(catecholate)

Marshall-Roth, Travis,Liebscher, Sean C.,Rickert, Karl,Seewald, Nicholas J.,Oliver, Allen G.,Brown, Seth N.

, p. 7826 - 7828 (2012)

Mechanistic studies indicate that the oxomolybdenum(vi) bis(3,5-di-tert-butylcatecholate) fragment deoxygenates pyridine-N-oxides in a reaction where the oxygen is delivered to molybdenum but the electrons for substrate reduction are drawn from the bound catecholate ligands, forming 3,5-di-tert-butyl-1,2-benzoquinone.

Synthesis of picolines over metal modified HZSM-5 catalyst

Jiang,Huang,Xiao,Xiao,Li

, p. 2415 - 2419 (2015)

A series of metal (i.e. Pb, Cd, Zn, Co, Cr) modified H-ZSM-5 catalysts were prepared by an ion-exchange method and were characterized by XRD, FT-IR, NH3-TPD and N2 adsorption techniques. There catalytic activity was evaluated in the Chichibabin condensation of acetaldehyde and ammonia giving 2-picoline, 4-picoline and a small amount of pyridine as the product. The catalyst coking behaviour was also characterized by TG measurement. The characterization results showed that the crystal structure of H-ZSM-5 was well reserved and the active metal ions were evenly spread in the ZSM-5 framework. The surface acidity was enhanced a lot after the metal modification. Catalytic results showed that metal incorporated catalysts greatly increased the total yield of pyridine bases, especially which of 2-picoline and 4-picoline, meanwhile the ratio of 2-picoline/4-picoline was also enhanced.

Synthesis of Pyridine Bases over Ion-exchanged Pentasil Zeolite

Sato, Hiroshi,Shimizu, Shinkichi,Abe, Nobuyuki,Hirose, Ken-ichi

, p. 59 - 62 (1994)

The catalytic activity of pentasil zeolite for the synthesis of pyridine bases from aldehydes and ammonia was found to depend upon the Si/Al ratio and the metal cation.The best choices are 30 to 120 of Si/Al ratios and metal cations Such as Tl(I), Pb(II), Co(II) and Zn(II).

Probing the nature of the Co(III) ion in corrins: Comparison of reactions of aquacyanocobyrinic acid heptamethyl ester and aquacyano-stable yellow cobyrinic acid hexamethyl ester with neutral N-donor ligands

Chemaly, Susan M.,Kendall, Louise,Nowakowska, Monika,Pon, Dale,Perry, Christopher B.,Marques, Helder M.

, p. 1077 - 1083 (2013)

Equilibrium constants (log K) for substitution of coordinated H 2O in aquacyanocobyrinic acid heptamethyl ester (aquacyanocobester, ACCbs) and aquacyano-stable yellow cobyrinic acid hexamethyl ester (aquacyano-stable yellow cobester, ACSYCbs), in which oxidation of the C5 carbon of the corrin interrupts the normal delocalized system of corrins, by neutral N-donor ligands (ammonia, ethanolamine, 2-methoxyethylamine, N-methylimidazole, and 4-methylpyridine) have been determined spectrophotometrically as a function of temperature. Log K values increase with the basicity of the ligand, but a strong compensation effect between ΔH and ΔS values causes a leveling effect. The aliphatic amines with a harder donor atom produce ΔH values that are more negative in their reactions with ACSYCbs than with ACCbs, while the softer, aromatic N donors produce more negative ΔH values with ACCbs than with ACSYCbs. Molecular modeling (DFT, M06L/SVP, and a quantum theory of atoms in molecules analysis of the electron density) shows that complexes of the aliphatic amines with SYCbs produce shorter and stronger Co-N bonds with less ionic character than the Co-N bonds of these ligands with the cobester. Conversely, the Co-N bond to the aromatic N donors is shorter, stronger, and somewhat less ionic in the complexes of the cobester than in those of the SYCbs. Therefore, the distinction between the harder Co(III) in ACSYCbs and softer Co(III) in ACCbs, reported previously for anionic ligands, is maintained for neutral N-donor ligands.

Basicity of pyridine and some substituted pyridines in ionic liquids

Angelini, Guido,De Maria, Paolo,Chiappe, Cinzia,Fontana, Antonella,Pierini, Marco,Siani, Gabriella

, p. 3912 - 3915 (2010)

Figure presented The equilibrium constants for ion pair formation of some pyridines have been evaluated by spectrophotometric titration with trifluoroacetic acid in different ionic liquids. The basicity order is the same in ionic liquids and in water. The substituent effect on the equilibrium constant has been discussed in terms of the Hammett equation. Pyridine basicity appears to be less sensitive to the substituent effect in ionic liquids than in water.

Ionic Liquids as “Masking” Solvents of the Relative Strength of Bases in Proton Transfer Reactions

Zappacosta, Romina,Di Crescenzo, Antonello,Ettorre, Valeria,Fontana, Antonella,Pierini, Marco,Siani, Gabriella

, p. 35 - 41 (2018)

Equilibrium constants for the proton transfer reaction between pyridines and trifluoroacetic acid were measured in room-temperature ionic liquids (ILs) of different cation–anion compositions. The experimental equilibrium constants for ion-pair formation were corrected according to the Fuoss equation. The calculated equilibrium constants for the formation of free ions were taken as a quantitative measure of the base strength in IL solutions and compared with the relative constants in water. The effect of IL composition is discussed for a series of fixed IL anions and fixed IL cations. Finally, the sensitivity of the proton transfer reaction to the electronic effects of the substituent groups on the pyridine ring was quantified by applying the Hammett equation. A more marked levelling effect on the base strength was observed in ILs than in water. The Hammett reaction constants ρ were then correlated with solvent parameters according to a multi-parametric analysis, which showed that both specific hydrogen-bond donor/acceptor and non-specific interactions play an important role, with α and permittivity being the main parameters affecting the ability of the IL to differentiate the strength of the base.

Solvent dependence of oxygen isotope effects on the decarboxylation of 4-pyridylacetic acid

Headley, George W.,O'Leary, Marion H.

, p. 1894 - 1896 (1990)

Oxygen isotope effects on the decarboxylation of 4-pyridylacetic acid have been measured by the remote-label technique. The isotope effect varies from k16/k18 = 0.995 per oxygen in 25% dioxane to 1.003 in 75% dioxane. The isotope effect reflects three contributions: An inverse isotope effect of 0.98-0.99 due to the change in carbon-oxygen bond order on going from ground state to transition state, an effect of 1.01-1.02 due to desolvation of the carboxyl group, and an effect of approximately 1.01 due to the acid-base equilibrium of the carboxyl group. Thus, oxygen isotope effects on decarboxylation should be a useful probe for carboxyl desolvation in enzymatic decarboxylations.

-

Hughes et al.

, p. 3327 (1974)

-

-

Akhemerov et al.

, (1975)

-

Catalytic Deoxygenation of Amine and Pyridine N-Oxides Using Rhodium PCcarbeneP Pincer Complexes

Tinnermann, Hendrik,Sung, Simon,Cala, Beatrice A.,Gill, Hashir J.,Young, Rowan D.

, p. 797 - 803 (2020)

Rhodium PCcarbeneP pincer complexes 1-L (L = PPh3, PPh2(C6F5), PCy3) readily facilitate deoxygenation of amine and pyridine N-oxides. The resulting complexes exhibit δ2-C= O coordination of the resulting keto POP pincer ligand. These δ2-Ca? O linkages in the metalloepoxide complexes are readily reduced by isopropyl alcohol and various benzylic alcohols. Thus, efficient catalytic deoxygenation of amine and pyridine N-oxides is possible using complexes 1-L and isopropyl alcohol. This represents a pioneering example of PCcarbeneP pincer complexes being used as catalysts for catalytic deoxygenation.

Activation of rhenium(I) toward substitution in fac -[Re(N,O′ -Bid)(CO)3(HOCH3)] by Schiff-base bidentate ligands (N,O′ -Bid)

Brink, Alice,Visser, Hendrik G.,Roodt, Andreas

, p. 8950 - 8961 (2013)

A series of fac-[Re(N,O′-Bid)(CO)3(L)] (N,O′-Bid = monoanionic bidentate Schiff-base ligands with N,O donor atoms; L = neutral monodentate ligand) has been synthesized, and the methanol substitution reactions have been investigated. The complexes were characterized by NMR, IR, and UV-vis spectroscopy. X-ray crystal structures of the compounds fac-[Re(Sal-mTol)(CO)3(HOCH3)], fac-[Re(Sal-pTol)(CO) 3(HOCH3)], fac-[Re(Sal-Ph)(CO)3(HOCH 3)], and fac-[Re(Sal-Ph)(CO)3(Py)] (Sal-mTol = 2-(m-tolyliminomethyl)phenolato; Sal-pTol = 2-(p-tolyliminomethyl)phenolato; Sal-Ph = 2-(phenyliminomethyl)phenolato; Py = pyridine) are reported. Significant activation for the methanol substitution is induced by the use of the N,O bidentate ligand as manifested by the second order rate constants, with limiting kinetics being observed for the first time. Rate constants (25 C) (k1 or k3) and activation parameters (ΔH ka, kJ mol-1; ΔS ka, J K-1 mol-1) from Eyring plots for entering nucleophiles as indicated are as follows: fac-[Re(Sal-mTol)(CO)3(HOCH3)] 3-chloropyridine: (k 1) 2.33 ± 0.01 M-1 s-1; 85.1 ± 0.6, 48 ± 2; fac-[Re(Sal-mTol)(CO)3(HOCH3)] pyridine: (k1) 1.29 ± 0.02 M-1 s-1; 92 ± 2, 66 ± 7; fac-[Re(Sal-mTol)(CO)3(HOCH3)] 4-picoline: (k1) 1.27 ± 0.05 M-1 s-1; 88 ± 2, 53 ± 6; (k3) 3.9 ± 0.03 s-1; 78 ± 8, 30 ± 27; (kf) 1.7 ± 0.02 M-1 s-1; 86 ± 2, 49 ± 6; fac-[Re(Sal-mTol)(CO) 3(HOCH3)] DMAP (k3) 1.15 ± 0.02 s -1; 88 ± 2, 52 ± 7. An interchange dissociative mechanism is proposed.

Casabo, J.,Colomer, J.,Llobet, A.,Teixidor, F,Molins, E.,Miravitlles, C

, p. 2743 - 2748 (1989)

1,4-dioxobenzene compounds of gallium: Reversible binding of pyridines to [{(tBu)2Ga}2(μ-OC6H 4O)]n in the solid state

Van Poppel, Laura H.,Bott, Simon G.,Barron, Andrew R.

, p. 11006 - 11017 (2003)

The gallium aryloxide polymer, [{(tBu)2Ga} 2(μ-OC6H4O)]n (1) is synthesized by the addition of Ga(tBu)3 with hydroquinone in a noncoordinating solvent, and reacts with pyridines to yield the yellow compound [(tBu)2Ga(L)]2(μ-OC6H 4O) [L = py (2), 4-Mepy (3), and 3,5-Me2py (4)] via cleavage of the Ga2O2 dimeric core. The analogous formation of Ga(tBu)2(OPh)(py) (5) occurs by dissolution of [(tBu)2Ga(μ-OPh)]2 in pyridine. In solution, 2-4 undergo dissociation of one of the pyridine ligands to yield [(tBu)2Ga(L)(μ-OC6H4O)Ga( tBu)2]2, for which the ΔH and ΔS have been determined. Thermolysis of compounds 2-4 in the solid-state results in the loss of the Lewis base and the formation of 1. The reaction of 1 or [(tBu)2Ga-(μ-OPh)]2 with the vapor of the appropriate ligand results in the solid state formation of 2-4 or 5, respectively. The ΔH? and ΔS? for both ligand dissociation and association for the solid-vapor reactions have been determined. The interconversion of 1 into 2-4, as well as [(tBu) 2Ga(μ-OPh)]2 into 5, and their reverse reactions, have been followed by 13C CPMAS NMR spectroscopy, TG/DTA, SEM, EDX, and powder XRD. Insight into this solid-state polycondensation polymerization reaction may be gained from the single-crystal X-ray crystallographic packing diagrams of 2-5. The crystal packing for compounds 2, 3, and 5 involve a head-to-head arrangement that is maintained through repeated ligand dissociation and association cycles. In contrast, when compound 4 is crystallized from solution a head-to-tail packing arrangement is formed, but during reintroduction of 3,5-Me2py in the solid state-vapor reaction of compound 1, a head-to-head polymorph is postulated to account for the alteration in the ΔH? of subsequent ligand dissociation reactions. Thus, the ΔH? for the condensation polymerization reaction is dependent on the crystal packing; however, the subsequent reversibility of the reaction is dependent on the polymorph.

HETEROGENIZED TRANSITION METAL COMPLEXES AS CATALYSTS FOR SYNTHESIZING METHYLPYRIDINES FROM ACETALDEHYDE AND AMMONIA

Chekurovskaya, E. D.,Akimov, A. N.,Tarasova, T. M.

, p. 663 - 667 (1993)

The synthesis of methylpyridines from acetaldehyde and ammonia in the presence of N- and F-containing heterogenized transition metal complexes is studied by a pulse microcatalytic method.A correlation between the donor-acceptor properties of the ligand, of the complexed metal, and of the catalytically active complex is found using 31P NMR.The reaction direction depends on the properties of the solvent used to heterogenize the complex on the carrier.

Bifunctional Mechanism of Pyridine Hydrodenitrogenation

Marzari, J. A.,Rajagopal, S.,Miranda, R.

, p. 255 - 264 (1995)

The role of Mo coordinatively unsaturated sites (CUS) and Broensted acidic sites in the hydrodenitrogenation of pyridine was investigated in an atmospheric-pressure microreactor.The test catalysts consisted of nonsulfided Mo oxide supported on Al2O3, SiO2, and silica-aluminas, containing different concentrations of Mo CUS and Broensted acidic sites.The kinetic study revealed that Mo loading and support composition affect the specific activity of Mo and selectivity of the catalysts.For the range of conditions used in this study (360-420 deg C, 1 atm H2, 0.2 molpercent pyridine concentration, differential conversion), the most abundant reaction intermediate was trans-2-pentene, and the rate-limiting step was the hydrogenation of the ring.Thus, the overall activity was correlated with the concentration of Mo CUS, which are the hydrogenation sites.The yield of denitrogenated product was also correlated with concentration of CUS.The Broensted acidic sites determined the selectivity towards the observed cracking, isomerization, and alkylation products.

Clean protocol for deoxygenation of epoxides to alkenes: Via catalytic hydrogenation using gold

Fiorio, Jhonatan L.,Rossi, Liane M.

, p. 312 - 318 (2021/01/29)

The epoxidation of olefin as a strategy to protect carbon-carbon double bonds is a well-known procedure in organic synthesis, however the reverse reaction, deprotection/deoxygenation of epoxides is much less developed, despite its potential utility for the synthesis of substituted olefins. Here, we disclose a clean protocol for the selective deprotection of epoxides, by combining commercially available organophosphorus ligands and gold nanoparticles (Au NP). Besides being successfully applied in the deoxygenation of epoxides, the discovered catalytic system also enables the selective reduction N-oxides and sulfoxides using molecular hydrogen as reductant. The Au NP catalyst combined with triethylphosphite P(OEt)3 is remarkably more reactive than solely Au NPs. The method is not only a complementary Au-catalyzed reductive reaction under mild conditions, but also an effective procedure for selective reductions of a wide range of valuable molecules that would be either synthetically inconvenient or even difficult to access by alternative synthetic protocols or by using classical transition metal catalysts. This journal is

Metal-Free Deoxygenation of Amine N-Oxides: Synthetic and Mechanistic Studies

Lecroq, William,Schleinitz, Jules,Billoue, Mallaury,Perfetto, Anna,Gaumont, Annie-Claude,Lalevée, Jacques,Ciofini, Ilaria,Grimaud, Laurence,Lakhdar, Sami

, p. 1237 - 1242 (2021/06/01)

We report herein an unprecedented combination of light and P(III)/P(V) redox cycling for the efficient deoxygenation of aromatic amine N-oxides. Moreover, we discovered that a large variety of aliphatic amine N-oxides can easily be deoxygenated by using only phenylsilane. These practically simple approaches proceed well under metal-free conditions, tolerate many functionalities and are highly chemoselective. Combined experimental and computational studies enabled a deep understanding of factors controlling the reactivity of both aromatic and aliphatic amine N-oxides.

α-Heteroarylation of Thioethers via Photoredox and Weak Br?nsted Base Catalysis

Alfonzo, Edwin,Hande, Sudhir M.

, p. 6115 - 6120 (2021/08/16)

We report the C-H activation of thioethers to α-thio alkyl radicals and their addition to N-methoxyheteroarenium salts for the redox-neutral synthesis of α-heteroaromatic thioethers. Studies are consistent with a two-step activation mechanism, where oxidation of thioethers to sulfide radical cations by a photoredox catalyst is followed by α-C-H deprotonation by a weak Br?nsted base catalyst to afford α-thio alkyl radicals. Further, N-methoxyheteroarenium salts play additional roles as a source of methoxyl radical that contributes to α-thio alkyl radical generation and a sacrificial oxidant that regenerates the photoredox catalytic cycle.

Photocatalytic deoxygenation of N-O bonds with rhenium complexes: From the reduction of nitrous oxide to pyridineN-oxides

Anthore-Dalion, Lucile,Cantat, Thibault,Kjellberg, Marianne,Nicolas, Emmanuel,Ohleier, Alexia,Thuéry, Pierre

, p. 10266 - 10272 (2021/08/12)

The accumulation of nitrogen oxides in the environment calls for new pathways to interconvert the various oxidation states of nitrogen, and especially their reduction. However, the large spectrum of reduction potentials covered by nitrogen oxides makes it difficult to find general systems capable of efficiently reducing variousN-oxides. Here, photocatalysis unlocks high energy species able both to circumvent the inherent low reactivity of the greenhouse gas and oxidant N2O (E0(N2O/N2) = +1.77 Vvs.SHE), and to reduce pyridineN-oxides (E1/2(pyridineN-oxide/pyridine) = ?1.04 Vvs.SHE). The rhenium complex [Re(4,4′-tBu-bpy)(CO)3Cl] proved to be efficient in performing both reactions under ambient conditions, enabling the deoxygenation of N2O as well as synthetically relevant and functionalized pyridineN-oxides.

A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics

García-Domínguez, Andrés,Gonzalez, Jorge A.,Leach, Andrew G.,Lloyd-Jones, Guy C.,Nichol, Gary S.,Taylor, Nicholas P.

supporting information, (2022/01/04)

The kinetics of quinuclidine displacement of BH3 from a wide range of Lewis base borane adducts have been measured. Parameterization of these rates has enabled the development of a nucleofugality scale (NFB), shown to quantify and predict the leaving group ability of a range of other Lewis bases. Additivity observed across a number of series R′3-nRnX (X = P, N; R′ = aryl, alkyl) has allowed the formulation of related substituent parameters (nfPB, nfAB), providing a means of calculating NFB values for a range of Lewis bases that extends far beyond those experimentally derived. The utility of the nucleofugality parameter is explored by the correlation of the substituent parameter nfPB with the hydrolyses rates of a series of alkyl and aryl MIDA boronates under neutral conditions. This has allowed the identification of MIDA boronates with heteroatoms proximal to the reacting center, showing unusual kinetic lability or stability to hydrolysis.

Process route upstream and downstream products

Process route

4-methyl-1-(4-nitro-phenoxythiocarbonyl)-pyridinium; chloride

4-methyl-1-(4-nitro-phenoxythiocarbonyl)-pyridinium; chloride

picoline
108-89-4

picoline

carbon oxide sulfide
463-58-1

carbon oxide sulfide

Conditions
Conditions Yield
With phosphate buffer; potassium chloride; In water; at 25 ℃; pH=6.5; Further Variations:; pH-values; Kinetics;
copper(I) cyanide
544-92-3

copper(I) cyanide

3-Bromo-4-methylpyridin
3430-22-6

3-Bromo-4-methylpyridin

picoline
108-89-4

picoline

3-cyano-4-methylpyridine
5444-01-9

3-cyano-4-methylpyridine

Conditions
Conditions Yield
With sodium cyanide; In water; N,N-dimethyl-formamide; a) reflux, 3 h, b) steam bath, 2 h;
30%
4-(2-chloro-1,1-diphenylethyl)pyridine
29958-05-2

4-(2-chloro-1,1-diphenylethyl)pyridine

picoline
108-89-4

picoline

4-(1,1-diphenylethyl)pyridine
109975-61-3

4-(1,1-diphenylethyl)pyridine

4-(1,2-diphenylethyl)pyridine
6634-61-3

4-(1,2-diphenylethyl)pyridine

Diphenylmethane
101-81-5

Diphenylmethane

Conditions
Conditions Yield
With ethanol; lithium; Multistep reaction. Further byproducts given; 1.) THF, 25 deg C, 48 h;
4-(2-chloro-1,1-diphenylethyl)pyridine
29958-05-2

4-(2-chloro-1,1-diphenylethyl)pyridine

picoline
108-89-4

picoline

4-(1,1-diphenylethyl)pyridine
109975-61-3

4-(1,1-diphenylethyl)pyridine

4-(1,2-diphenylethyl)pyridine
6634-61-3

4-(1,2-diphenylethyl)pyridine

diphenyl-4-pyridylmethane
3678-72-6

diphenyl-4-pyridylmethane

Diphenylmethane
101-81-5

Diphenylmethane

Conditions
Conditions Yield
With lithium; In tetrahydrofuran; at 25 ℃; for 48h; Product distribution; Mechanism; other solvent, other alkali metal as reagent; other phenyl and pyridyl substituted ethanes;
rac-1-phenyl-2-(4-pyridyl)ethanol
20151-37-5

rac-1-phenyl-2-(4-pyridyl)ethanol

picoline
108-89-4

picoline

trans-4-styrylpyride
5097-93-8

trans-4-styrylpyride

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
In various solvent(s); at 170 ℃; Kinetics; Mechanism; deuterated substrate;
70 % Spectr.
30 % Spectr.
70 % Spectr.
{C<sub>6</sub>H<sub>6</sub>NCr(H<sub>2</sub>O)5}<sup>(2+)</sup>

{C6H6NCr(H2O)5}(2+)

picoline
108-89-4

picoline

1,2-bis(4'-pyridyl)ethane
4916-57-8

1,2-bis(4'-pyridyl)ethane

Conditions
Conditions Yield
In perchloric acid; addn. of Na2CO3;;
30%
70%
With sodium carbonate; byproducts: pyridine-4-aldehyde;
20%
With Na2CO3;
In perchloric acid;
pyridine
110-86-1

pyridine

2-iodo-propane
75-30-9

2-iodo-propane

picoline
108-89-4

picoline

4-s-propylpyridine
696-30-0

4-s-propylpyridine

Conditions
Conditions Yield
at 200 - 240 ℃; for 16h; autoclave;
5%
7%
4-Ethylpyridine
536-75-4,151103-55-8

4-Ethylpyridine

pyridine
110-86-1

pyridine

picoline
108-89-4

picoline

(pyridin-4-yl)-α-methylstyrene
17755-30-5

(pyridin-4-yl)-α-methylstyrene

4-s-propylpyridine
696-30-0

4-s-propylpyridine

Conditions
Conditions Yield
With γ-Al2O3; at 500 ℃; Further Variations:; Reagents; Temperatures; Product distribution;
0.7%
19.9%
15.8%
0.5%
pyridine
110-86-1

pyridine

methanol
67-56-1

methanol

α-picoline
109-06-8

α-picoline

picoline
108-89-4

picoline

2,6-dimethylpyridine
108-48-5

2,6-dimethylpyridine

4-Ethylpyridine
536-75-4,151103-55-8

4-Ethylpyridine

Conditions
Conditions Yield
cation-exchanged zeolite; at 400 ℃;
6.8 % Chromat.
2.3 % Chromat.
2.5 % Chromat.
0.6 % Chromat.
pyridine
110-86-1

pyridine

methanol
67-56-1

methanol

α-picoline
109-06-8

α-picoline

picoline
108-89-4

picoline

2-Ethylpyridine
100-71-0

2-Ethylpyridine

4-Ethylpyridine
536-75-4,151103-55-8

4-Ethylpyridine

3-Methylpyridine
108-99-6

3-Methylpyridine

Conditions
Conditions Yield
Cs exchanged zeolite; at 450 ℃; Product distribution; investigation of the heterogeneous vapor-phase alkylation of pyridine with methanol over Na+, K+, Rb+, or Cs+ exchanged X- or Y-type zeolite in an atmosphere of nitrogen;
22.2%
6.5%
5.5%
5.3%
5%
3.1%

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