4-Methylpyridine

Base Information

• Chemical Name: 4-Methylpyridine
• CAS No.: 108-89-4
• Deprecated CAS: 82005-09-2,92075-35-9
• Molecular Formula: C6H7N
• Molecular Weight: 93.1283
• Hs Code.: 29333955
• European Community (EC) Number: 203-626-4
• ICSC Number: 0803
• NSC Number: 18252
• UN Number: 2313
• UNII: TJD6V9SSO7
• DSSTox Substance ID: DTXSID4021892
• Nikkaji Number: J5.084I
• Wikipedia: 4-Methylpyridine
• Wikidata: Q2189778
• Metabolomics Workbench ID: 54619
• ChEMBL ID: CHEMBL15544
• Mol file: 108-89-4.mol

Synonyms:4-methylpyridine;4-methylpyridinium

Chemical Property of 4-Methylpyridine

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 4 mm Hg ( 20 °C)
• Melting Point: 2.4 °C(lit.)
• Refractive Index: n20/D 1.504(lit.)
• Boiling Point: 144.2 °C at 760 mmHg
• PKA: 6.02(at 20℃)
• Flash Point: 40 °C
• PSA: 12.89000
• Density: 0.95 g/cm³
• LogP: 1.39000
• Storage Temp.: Flammables area
• Sensitive.: Air Sensitive & Hygroscopic
• Solubility.: alcohol: soluble(lit.)
• Water Solubility.: soluble
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 93.057849228
• Heavy Atom Count: 7
• Complexity: 46.1
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

4-Methylpyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 10-20/22-24-36/37/38
• Safety Statements: 26-36-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: CC1=CC=NC=C1
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is corrosive to the eyes and skin. The vapour is irritating to the respiratory tract. Exposure at high levels could cause unconsciousness.
• Effects of Long Term Exposure: The substance defats the skin, which may cause dryness or cracking.
• Uses: 4-Methylpyridine is used to manufacture isonicotinic acid and derivatives, in waterproofing agents for fabric, and as a solvent for resins, pharmaceuticals, dyestuffs, rubber accelerators, and pesticides. It is also used as a catalyst and curing agent. 4-Methylpyridine was used in the preparation of a 1,2-dihydropyridide derivative.

Technology Process of 4-Methylpyridine

There total 272 articles about 4-Methylpyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

benzyltri(2-(4-methylpyridyl))phosphonium bromide (126963-91-5) → picoline (108-89-4) + [2,2]bipyridinyl (366-18-7) + 4,4'-dimethyl-2,2'-bipyridines (1134-35-6)

Guidance literature:

With hydrogenchloride; In water; for 0.5h; Product distribution; Ambient temperature; variation of pH, temp. and time;

DOI:10.1016/S0040-4039(01)93895-X

Reference yield: 52.0%

1-o-Nitrobenzyl-4-methylpyridinium bromide → picoline (108-89-4) + 1-methyl-2-nitrobenzene (88-72-2)

Guidance literature:

With tetraethylammonium perchlorate; In acetonitrile; at 20 ℃; Rate constant; electrolyse, -0.89 V;

Reference yield: 30.0%

copper(I) cyanide (544-92-3) + 3-Bromo-4-methylpyridin (3430-22-6) → picoline (108-89-4) + 3-cyano-4-methylpyridine (5444-01-9)

Guidance literature:

With sodium cyanide; In water; N,N-dimethyl-formamide; a) reflux, 3 h, b) steam bath, 2 h;

DOI:10.1021/jm00050a006

upstream raw materials:

exo-1-azabicyclo[2.2.1]heptane

pyridine

methanol

lead(IV) tetraacetate

Downstream raw materials:

1,3-di(4-pyridyl)propane

trans-1,2-bis(pyridin-4-yl)ethene

4-Methyl-3,3'-bipyridin

4-methyl-2,3′-bipyridine

Refernces

• 1、 Coombes, R. G.,Johnson, M. D.,Tobe, M. L.,Winterton, N.,Wong, L. Y.. "". . . Retrieved 1965.
• 2、 Lozano,de Jesús,Lozano. "Synthesis, spectral, thermal and kinetic studies on the adducts with pyridines of tungsten(V) binuclear thiocomplexes with di-isopropyl-dithiocarbamate". . p. 3127 - 3132. Retrieved 2006.
• 3、 Suzuki, Masaaki,Sumi, Kengo,Koyama, Hiroko,Siqin,Hosoya, Takamitsu,Takashima-Hirano, Misato,Doi, Hisashi. "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". . p. 12489 - 12495. Retrieved 2009.
• 4、 Tschitschibabin. "-". . p. 1623. Retrieved 1937.
• 5、 Luo, Cai-Wu,Chao, Zi-Sheng. "Unsaturated aldehydes: a novel route for the synthesis of pyridine and 3-picoline". . p. 54090 - 54101. Retrieved 2015.
• 6、 Perez,Sanchez,Garcia,Serrano,Lopez. "Thermal study of [Pd(2-Phpy)Cl(L)] complexes (L=pyridines and amines)". . p. 361 - 370. Retrieved 2001.
• 7、 Coombes,Johnson. "". . p. 177. Retrieved 1966.
• 8、 Khamidullaev,Yusupov. "Properties of mixed polyfunctional fluoride catalysts for synthesis of pyridine bases from acetylene and ammonia (methanol)". . p. 939 - 942. Retrieved 2003.
• 9、 Konishi, Kazuyori,Matsumoto, Hiroshi,Saito, Katsuhiro,Takahashi, Kensuke. "NMR Studies of Picolyl-type Carbanions. VIII. Anions Produced by Reactions of Alkyl-substituted Pyridines with Butyllithium". . p. 2294 - 2297. Retrieved 1985.
• 10、 Brotzel, Frank,Kempf, Bernhard,Singer, Thomas,Zipse, Hendrik,Mayr, Herbert. "Nucleophilicities and carbon basicities of pyridines". . p. 336 - 345. Retrieved 2007.