3-Methylpyridine

Base Information

• Chemical Name: 3-Methylpyridine
• CAS No.: 108-99-6
• Deprecated CAS: 82005-08-1,2022918-42-7
• Molecular Formula: C6H7N
• Molecular Weight: 93.1283
• Hs Code.: 29333999
• European Community (EC) Number: 203-636-9
• ICSC Number: 0802
• NSC Number: 18251
• UN Number: 2313
• UNII: B083J4KF7F
• DSSTox Substance ID: DTXSID9021897
• Nikkaji Number: J5.085G
• Wikipedia: 3-Methylpyridine
• Wikidata: Q2697560
• Metabolomics Workbench ID: 52237
• ChEMBL ID: CHEMBL15722
• Mol file: 108-99-6.mol

Synonyms:3-methylpyridine;beta-picoline

Chemical Property of 3-Methylpyridine

Chemical Property:

• Appearance/Colour: Colorless liquid with a sweetish odor
• Vapor Pressure: 4.4 mm Hg ( 20 °C)
• Melting Point: -19 °C(lit.)
• Refractive Index: n20/D 1.504(lit.)
• Boiling Point: 143.516 °C at 760 mmHg
• PKA: 5.68(at 20℃)
• Flash Point: 36.111 °C
• PSA: 12.89000
• Density: 0.957 g/cm³
• LogP: 1.39000
• Storage Temp.: Flammables area
• Solubility.: alcohol: miscible(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: 52.1
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

3-Methylpyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,C
• Hazard Codes: C,Xn
• Statements: 10-20/21/22-34-36/37/38-22
• Safety Statements: 16-26-36/37/39-45-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: CC1=CN=CC=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: A useful precursor to agrochemicals and antidotes for organophosphate poisoning. Solvent; intermediate in the dye and resins industries; in the manufacture of insecticides, waterproofing agents, niacin, and niacinamide. 3-Picoline is used as a precursor in pharmaceuticals and agricultural industries. It acts as a precursor to 3-cyanopyridine, niacin, vitamin-B. It is an antidote for organophosphate poisoning.

Technology Process of 3-Methylpyridine

There total 205 articles about 3-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: 61.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + acetaldehyde (75-07-0,9002-91-9) → pyridine (110-86-1) + 3,5-Lutidine (591-22-0) + 3-ethylpyridine (536-78-7,151103-56-9) + 5-ethyl-2-methyl-pyridine (104-90-5) + 3-Methylpyridine (108-99-6) + 2,5-dimethylpyridine (589-93-5)

Guidance literature:

With diammonium phosphate; at 230 ℃; for 1.5h; under 26252.1 - 27752.2 Torr; Product distribution; investigation of the synthesis of pyridines from mixtures aldehydes;

DOI:10.1002/hlca.19840670811

Reference yield: 25.0%

2-methylcadaverine (15520-10-2) → pyridine-3-carbonitrile (100-54-9,121697-66-3,1232169-17-3,68271-95-4) + 3-Methylpyridine (108-99-6)

Guidance literature:

With ammonia; oxygen; V₂O₅/hydrotalcite; In water; at 425 ℃; for 1.5 - 4h; Product distribution / selectivity;

Reference yield: 22.2%

pyridine (110-86-1) + methanol (67-56-1) → 2-vinylpyridine (100-69-6,25014-15-7,27476-03-5,329041-71-6) + α-picoline (109-06-8) + picoline (108-89-4) + 2-Ethylpyridine (100-71-0) + 4-Ethylpyridine (536-75-4,151103-55-8) + 3-Methylpyridine (108-99-6)

Guidance literature:

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;

upstream raw materials:

brucine

α-picoline

picoline

nicotinyl chloride

Downstream raw materials:

2-[1-(2,6-dichloro-benzyl)-3-methyl-1H-pyridin-4-ylidene]-indan-1,3-dione

4-(3-phenylpropyl)-pyridine

2-(4-Chloroyphenyl)<1H>-pyrrolo<2,3-b>pyridine

3,5-Lutidine

Refernces

• 1、 Raja Ram,Purushothama Chary,Iyengar. "An efficient and chemoselective deoxygenation of hetero cyclic N-oxides using LiCl/NaBH4". . p. 3511 - 3515. Retrieved 2000.
• 2、 Luo, Cai-Wu,Feng, Xiao-Yan,Chao, Zi-Sheng. "Microwave-accelerated direct synthesis of 3-picoline from glycerol through a liquid phase reaction pathway". . p. 8863 - 8871. Retrieved 2016.
• 3、 Cullum, Neil R.,Renfrew, A. Hunter M.,Rettura, Donatella,Taylor, John A.,Whitmore, James M. J.,Williams, Andrew. "Effective charge on the nucleophile and leaving group during the stepwise transfer of the triazinyl group between pyridines in aqueous solution". . p. 9200 - 9205. Retrieved 1995.
• 4、 Bourne, Nicholas,Williams, Andrew. "Evidence for a Single Transition State in the Transfer of the Phosphoryl Group (-PO32-) to Nitrogen Nucleophiles from Pyridino-N-phosphonates". . p. 7591 - 7596. Retrieved 1984.
• 5、 Woodward et al.. "-". . p. 911,913. Retrieved 1944.
• 6、 Levy,Othmer. "-". . p. 789,793. Retrieved 1955.
• 7、 Palmer,Lossing. "-". . p. 1733. Retrieved 1963.
• 8、 Kamiguchi, Satoshi,Kajio, Ryu,Yamada, Hitomi,Yuge, Hidetaka,Okumura, Kazu,Iida, Hajime,Nagashima, Sayoko,Chihara, Teiji. "Thermal activation of solid-state molybdenum halide clusters with an octahedral cluster framework and their application to catalytic synthesis of 3-methylpyridine from piperidine and methanol". . p. 1116 - 1122. Retrieved 2015.
• 9、 Grigor'eva, Nellya G.,Filippova, Nadezhda A.,Agliullin, Marat R.,Kutepov, Boris I.,Narender, Nama. "Crystalline and amorphous aluminosilicates with different pore structures for the synthesis of pyridines". . p. 253 - 261. Retrieved 2017.
• 10、 Giam,Abbott. "-". . p. 1294. Retrieved 1971.