5-Hydroxy-2-methylpyridine

Base Information

• Chemical Name: 5-Hydroxy-2-methylpyridine
• CAS No.: 1121-78-4
• Molecular Formula: C6H7NO
• Molecular Weight: 109.128
• Hs Code.: 29333990
• European Community (EC) Number: 214-337-8
• NSC Number: 27963
• UNII: UKE16JP1JR
• DSSTox Substance ID: DTXSID4051580
• Nikkaji Number: J121J
• Wikidata: Q27291117
• ChEMBL ID: CHEMBL134979
• Mol file: 1121-78-4.mol

Synonyms:5-Hydroxy-2-methylpyridine;1121-78-4;6-Methylpyridin-3-ol;2-Methyl-5-hydroxypyridine;3-HYDROXY-6-METHYLPYRIDINE;6-Methyl-3-pyridinol;3-Pyridinol, 6-methyl-;6-Methyl-3-hydroxypyridine;5-Hydroxy-2-picoline;2-methyl-5-pyridinol;2-methyl-5-hydroxy pyridine;EINECS 214-337-8;UNII-UKE16JP1JR;MFCD00006339;NSC 27963;UKE16JP1JR;BRN 0107077;DTXSID4051580;NSC-27963;5-21-02-00139 (Beilstein Handbook Reference);1198167-15-5;2-methyl-5-hydroxy-pyridine;5-hydroxypicoline;6-Methyl-pyridin-3-ol;6-methyl-pyridine-3-ol;2-methyl-5hydroxypyridine;5-hydroxy-2-methylpridine;3-hydroxy-6-methyl pyridine;3-hydroxy-6-methyl-pyridine;5-hydroxy-2-methyl pyridine;5-hydroxy-2-methyl-pyridine;6-methyl-3-hydroxy-pyridine;SCHEMBL104940;CHEMBL134979;3-PYRIDOL, 6-METHYL-;DTXCID8030132;DHLUJPLHLZJUBW-UHFFFAOYSA-;5-Hydroxy-2-methylpyridine, 99%;NSC27963;STR03888;Tox21_304013;CL0058;AKOS007930884;HYDROXY-6-METHYLPYRIDINE, 3-;AC-5086;CS-W004681;PB30543;NCGC00357226-01;BP-10108;SY007644;CAS-1121-78-4;LS-133011;AM20061678;FT-0620467;H0763;EN300-55469;AC-907/25014124;W-204773;Q27291117;F0001-0268;Z838078132

Chemical Property of 5-Hydroxy-2-methylpyridine

Chemical Property:

• Appearance/Colour: beige to light tan crystalline powder
• Vapor Pressure: 0.000846mmHg at 25°C
• Melting Point: 168-170 ºC(lit.)
• Refractive Index: 1.55
• Boiling Point: 295.8 ºC at 760 mmHg
• PKA: 9.49±0.10(Predicted)
• Flash Point: 132.7 ºC
• PSA: 33.12000
• Density: 1.12 g/cm³
• LogP: 1.09560
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: dichloromethane: soluble
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 109.052763847
• Heavy Atom Count: 8
• Complexity: 74.9

Purity/Quality:

98%, ^*data from raw suppliers

6-Methyl-3-pyridinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-40-36/37/38
• Safety Statements: 26-39-24/25-36-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=NC=C(C=C1)O
• Uses: 5-Hydroxy-2-methylpyridine was used as starting reagent for the synthesis of 5-[(4-methoxybenzyl)oxy]-2-pyridinecarbaldehyde. It was used in synthesis of [HNC6H6OH]2[Cu(NC5H5)4(NbOF5)2].It was used as ligand of a platinum complex which showed protein kinase inhibitory action at nanomolar levels. It forms a chiral pyridinium ionic liquid on reaction with L-menthol chloromethyl ether.

Technology Process of 5-Hydroxy-2-methylpyridine

There total 25 articles about 5-Hydroxy-2-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: 88.0%

5-bromo-2-methylpyridine (3430-13-5) → 5-Hydroxy-2-methylpyridine (1121-78-4)

Guidance literature:

With copper(l) iodide; cesium hydroxide; triethanolamine; tetrabutylammomium bromide; water; at 145 ℃; for 24h; Inert atmosphere;

DOI:10.1002/ejoc.201301370

Reference yield: 84.0%

5-methoxy-2-picoline (55270-47-8) → 5-Hydroxy-2-methylpyridine (1121-78-4)

Guidance literature:

With L-Selectride; In tetrahydrofuran; for 24h; chemoselective reaction; Reflux; Inert atmosphere;

DOI:10.1055/s-0037-1612427

Reference yield: 84.0%

6-methyl-1-tosyl-1,6-dihydropyridin-3-yl acetate → 5-Hydroxy-2-methylpyridine (1121-78-4)

Guidance literature:

6-methyl-1-tosyl-1,6-dihydropyridin-3-yl acetate; With potassium hydroxide; In tetrahydrofuran; methanol; at 70 ℃; for 0.5h;

With ammonium chloride; In tetrahydrofuran; methanol; water;

DOI:10.1039/c7cc02521a

upstream raw materials:

5-Methylfurfural

2-methylpyridine N-oxide

acetic anhydride

5-hydroxymethylfuran-2-ylmethylamine

Downstream raw materials:

5-methoxy-2-picoline

3-hydroxy-2-hydroxymethyl-6-methylpyridine

5-acetoxy-2-methylpyridine

diphenyl-carbamic acid-(6-methyl-[3]pyridyl ester)

Refernces

• 1、 Makino, Kosho,Hasegawa, Yumi,Inoue, Takahide,Araki, Koji,Tabata, Hidetsugu,Oshitari, Tetsuta,Ito, Kiyomi,Natsugari, Hideaki,Takahashi, Hideyo. "Chemoselective Demethylation of Methoxypyridine". . p. 951 - 954. Retrieved 2019/05/10.
• 2、 Wang, Deping,Kuang, Daizhi,Zhang, Fuxing,Tang, Siping,Jiang, Wujiu. "Triethanolamine as an inexpensive and efficient ligand for copper-catalyzed hydroxylation of aryl halides in water". supporting information. p. 315 - 318. Retrieved 2014/01/23.