2-Amino-4-methylpyridine

Base Information

• Chemical Name: 2-Amino-4-methylpyridine
• CAS No.: 695-34-1
• Deprecated CAS: 135995-51-6
• Molecular Formula: C6H8N2
• Molecular Weight: 108.143
• Hs Code.: 29333999
• European Community (EC) Number: 211-780-9
• NSC Number: 6972,1490
• UNII: 394N1Z644H
• DSSTox Substance ID: DTXSID1044720
• Nikkaji Number: J31.382C
• Wikidata: Q24755764
• Pharos Ligand ID: CVANRPTXYWSV
• ChEMBL ID: CHEMBL40833
• Mol file: 695-34-1.mol

Synonyms:2-amino-4-methylpyridine;2-amino-4-picoline;2-amino-4-picoline hydrochloride;2-amino-4-picoline nitrate;2-amino-4-picolinium;4-methyl-2-aminopyridine;Aminton;VMI 20-4

Chemical Property of 2-Amino-4-methylpyridine

Chemical Property:

• Appearance/Colour: Light yellow to brown flakes
• Vapor Pressure: 0.0778mmHg at 25°C
• Melting Point: 96-101 °C
• Refractive Index: 1.5560 (estimate)
• Boiling Point: 227.4 °C at 760 mmHg
• PKA: pK1: 7.48(+1) (25°C)
• Flash Point: 114 °C
• PSA: 38.91000
• Density: 1.068 g/cm³
• LogP: 1.55340
• Storage Temp.: Refrigerator
• Sensitive.: Hygroscopic
• Solubility.: DMF: freely soluble
• Water Solubility.: SOLUBLE
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 108.068748264
• Heavy Atom Count: 8
• Complexity: 72.9

Purity/Quality:

99% ^*data from raw suppliers

2-Amino-4-methylpyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 45-46-60-61-8-21-25-26-34-42/43-48/23-50/53-36/37/38-33-23/24/25
• Safety Statements: 53-45-60-61-37/39-28A-26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=NC=C1)N
• Uses: Intermediate, medicine. 2-Amino-4-methylpyridine has been used in the synthesis of 2-amino-4-methyl-pyridinium 2-hy-droxy-benzoate. It is potent inhibitor of NOS2 (iNOS) in vitro. It is used as pharmaceutical intermediate.

Technology Process of 2-Amino-4-methylpyridine

There total 17 articles about 2-Amino-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: 94.0%

2,2-dimethyl-3-(4-methylpyrid-2-yl)-4-oxo-4H-1,3-benzoxazine (76809-23-9) → 2-Amino-4-methylpyridine (695-34-1) + salicylic acid (69-72-7,25496-36-0,8052-31-1)

Guidance literature:

With hydrogenchloride; for 3h; Heating;

Reference yield: 91.0%

2-Bromo-4-picoline (4926-28-7) → 2-Amino-4-methylpyridine (695-34-1)

Guidance literature:

With ammonium hydroxide; L-2-O-methyl-chiro-inositol; copper(II) acetate monohydrate; In 1-methyl-pyrrolidin-2-one; at 110 ℃; for 20h;

DOI:10.1055/s-0039-1690707

Reference yield: 90.0%

4-methyl-2-nitropyridine (18368-71-3) → 2-Amino-4-methylpyridine (695-34-1)

Guidance literature:

With C₃₆H₅₆Cl₃CrN₂O; magnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In tetrahydrofuran; at 60 ℃; for 24h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/jacs.0c12318

upstream raw materials:

picoline

2-(2,5-dimethyl-pyrrol-1-yl)-4-methyl-pyridine

4-methyl(2-nitroso)pyridine

2,2-dimethyl-3-(4-methylpyrid-2-yl)-4-oxo-4H-1,3-benzoxazine

Downstream raw materials:

N-(4-methyl-2-pyridinyl)-3-oxobutanamide

7-[(4-methylpyridin-2-ylamino)phenylmethyl]quinolin-8-ol

2-cyano-3t-(2-imino-4-methyl-2H-[1]pyridyl)-acrylic acid ethyl ester

2-cyano-3-(4-methyl-pyridin-2-ylamino)-acrylic acid ethyl ester

Refernces

• 1、 Zhao, Lixing,Hu, Chenyang,Cong, Xuefeng,Deng, Gongda,Liu, Liu Leo,Luo, Meiming,Zeng, Xiaoming. "Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications". supporting information. p. 1618 - 1629. Retrieved 2021/01/25.
• 2、 Ronson, Thomas O.,Renders, Evelien,Van Steijvoort, Ben F.,Wang, Xubin,Wybon, Clarence C. D.,Prokopcová, Hana,Meerpoel, Lieven,Maes, Bert U. W.. "Ruthenium-Catalyzed Reductive Arylation of N-(2-Pyridinyl)amides with Isopropanol and Arylboronate Esters". supporting information. p. 482 - 487. Retrieved 2019/01/04.