1603-41-4

Basic information

• Product Name: 2-Amino-5-methylpyridine
• Synonyms: TIMTEC-BB SBB004353;2-Pyridinamine,5-methyl-;3-Picoline, 6-amino-;5-Methyl-2-aminopyridine;5-methyl-2-pyridinamin;5-Methyl-2-pyridinamine;5-Methyl-2-pyridylamine dine;6-Amino-3-picoline 2-Amino-5-picoline 5-Methyl-2-pyridylamine
• CAS NO: 1603-41-4
• Molecular Formula: C₆H₈N₂
• Molecular Weight: 108.14
• EINECS: 216-503-5
• Product Categories: Aromatics;Heterocycles;Building Blocks;C6;Chemical Synthesis;Heterocyclic Building Blocks;Heterocycle-Pyridine series;amine;VARIOUSAMINE;Pyridine;Pyridines, Pyrimidines, Purines and Pteredines;Pyridine series;Amines;Pyridines;Pyridines derivates
• Mol File: 1603-41-4.mol
• Article Data: 21

Chemical Properties

• Melting Point: 76-77 °C(lit.)
• Boiling Point: 227 °C(lit.)
• Flash Point: 118°C
• Appearance: White to light yellow/Crystalline Powder, Crystals or Flakes
• Density: 227
• Vapor Pressure: 0.0794mmHg at 25°C
• Refractive Index: 1,524-1,528
• Storage Temp.: Refrigerator
• Solubility: 1000g/l
• PKA: pK1: 7.22(+1) (25°C)
• Sensitive: Hygroscopic
• BRN: 107050
• CAS DataBase Reference: 2-Amino-5-methylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-methylpyridine(1603-41-4)
• EPA Substance Registry System: 2-Amino-5-methylpyridine(1603-41-4)

Safety Data

• Hazard Codes: T,Xi
• Statements: 23/24/25-36/37/38-25
• Safety Statements: 26-36/37/39-45-37/39-28A
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• RTECS: TJ5141000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1603-41-4(Hazardous Substances Data)

Usage

Chemical Properties

light yellow crystalline flakes

Uses

Intermediate.

Safety Profile

Poison by ingestion,subcutaneous, and skin contact routes. When heated todecomposition it emits toxic vapors of NOx.

Purification Methods

Crystallise it from acetone. [Beilstein 22/9 V 289.]

InChI:InChI=1/C6H8N2/c1-5-2-3-6(7)8-4-5/h2-4H,1H3,(H2,7,8)/p+1

Synthetic route

2-Bromo-5-methylpyridine → (5-methyl-pyridin-2-yl)amine (1603-41-4)

Conditions	Yield
With [Cu2(2,7-bis(pyridin-2-yl)-l,8-naphthyridine)(OH)(CF3COO)3]; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 120℃; for 16h; Sealed tube;	100%
With ammonium hydroxide; potassium phosphate; 1-(5,6,7,8-tetrahydroquinolin-8-yl)-2-methylpropan-1-one; copper(I) bromide In dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere; Sealed tube;	85%

3-Methylpyridine (108-99-6) → (5-methyl-pyridin-2-yl)amine (1603-41-4) + 3-methylpyridin-2-ylamine (1603-40-3)

Conditions	Yield
With sodium amide; xylene
With ammonia; sodium; ethanolamine In toluene at 60 - 170℃; under 22502.3 - 41254.1 Torr; Pressure; Temperature; Autoclave; Inert atmosphere; Large scale;	A 1928 g B 144 g

3-picoline-N-oxide (1003-73-2) → (5-methyl-pyridin-2-yl)amine (1603-41-4)

Conditions	Yield
With hydrogenchloride; 4-chloro-2-methyl-1,3-benzoxazin-2-yl polystyrene 1.) ethylene chloride, reflux, 24 h, 2.) reflux, 20 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: CH2Cl2 / Heating 2: conc. HCl View Scheme
Multi-step reaction with 2 steps 1: 84 percent / CHCl3 / 4 h / Heating 2: 98 percent / conc. HCl / 8 h / Heating View Scheme
With thionyl chloride; trimethylamine
With sodium hydroxide; thionyl chloride; hydrogen bromide; trimethylamine In dichloromethane; ethyl acetate

3-Methylpyridine (108-99-6) → (5-methyl-pyridin-2-yl)amine (1603-41-4)

Conditions	Yield
With sodium amide In ethanol at 66℃; for 2.16667h; Temperature; Reflux;
Multi-step reaction with 3 steps 1: acetic acid; dihydrogen peroxide / 6 h / 80 °C 2: dinitrogen pentoxide / dichloromethane / 4 h / 40 °C 3: zinc; formic acid / dichloromethane; methanol / 2 h / 75 °C View Scheme

2-chloro-5-methylpyridine (18368-64-4) → (5-methyl-pyridin-2-yl)amine (1603-41-4)

Conditions	Yield
With dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C50H70NO4PPdS; C50H70NO4PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 50℃; for 24h; Reagent/catalyst; Inert atmosphere;	75%

2-nitro-5-methylpyridine-N-oxide (100047-39-0) → (5-methyl-pyridin-2-yl)amine (1603-41-4)

Conditions	Yield
With formic acid; zinc In methanol; dichloromethane at 75℃; for 2h; Time; Temperature;

sodium sulfate (7757-82-6) + 2-dimethylamino-5-methylpyridine → (5-methyl-pyridin-2-yl)amine (1603-41-4)

Conditions	Yield
With pyridine; sodium hydroxide In dichloromethane; water

3-picoline-N-oxide (1003-73-2) + phosgene (75-44-5) + trimethyl-(5-methyl-pyridin-2-yl)-ammonium chloride → (5-methyl-pyridin-2-yl)amine (1603-41-4)

Conditions	Yield
With sodium hydroxide; hydrogen bromide; trimethylamine In ethyl acetate

diethyl (2-amino-5-methylpyridin-3-yl)phosphonate (1042146-82-6) → (5-methyl-pyridin-2-yl)amine (1603-41-4) + 2-amino-5-methyl-3-phosphanylpyridine (1244954-88-8)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 48h;	A n/a B 59%

Upstream product

• 108-99-6 3-Methylpyridine 
• 104712-04-1 2-nitroso-5-methyl-pyridine 
• 1003-73-2 3-picoline-N-oxide 
• 110-86-1 pyridine 
• 407-25-0 trifluoroacetic anhydride 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 541544-19-8 C₁₀H₁₄N₂O 
• 100047-39-0 2-nitro-5-methylpyridine-N-oxide 
• 36172-53-9 N,N-dimethyl-N′-(5-methylpyridin-2-yl)formimidamide 
• 18368-64-4 2-chloro-5-methylpyridine 
• 1042146-82-6 diethyl (2-amino-5-methylpyridin-3-yl)phosphonate 
• 3510-66-5 2-Bromo-5-methylpyridine 
• 17282-00-7 3-bromo-5-methylpyridin-2-amine 
• 762-04-9 phosphonic acid diethyl ester 

Downstream Products

• 149486-00-0 1-(5-Methyl-pyridin-2-yl)-3-phenethyl-thiourea 
• 149487-94-5 1-[2-(2,6-Difluoro-phenyl)-ethyl]-3-(5-methyl-pyridin-2-yl)-thiourea 
• 149488-39-1 1-[2-(2-Ethoxy-6-fluoro-phenyl)-ethyl]-3-(5-methyl-pyridin-2-yl)-thiourea 
• 159639-09-5 1,3-diphenyl-3-(5-methylpyridin-2-yl)aminopropan-1-one 
• 201146-10-3 3-Methyl-5-[N-(5-methyl-pyridin-2-yl)-formimidoylamino]-isoxazole-4-carboxylic acid (4-chloro-phenyl)-amide 
• 1053735-60-6 3-[(3aS,4R,8R,8aS)-4,8-Dibenzyl-2,2-dimethyl-7-(3-nitro-benzyl)-6-oxo-hexahydro-1,3-dioxa-5,7-diaza-azulen-5-ylmethyl]-N-(5-methyl-pyridin-2-yl)-benzamide 
• 191218-50-5 2-(4-chlorophenyl)-7-methyl-4H-pyrido[1,2-a]pyrimidin-4-one 
• 1074-38-0 5-methyl-2-nitropyridine 
• 345340-50-3 N-2-(5-picolylamino)-N'-(2-methoxyphenyl)thiourea 

Relevant articles and documents

Mild, General, and Regioselective Synthesis of 2-Aminopyridines from Pyridine N -Oxides via N -(2-Pyridyl)pyridinium Salts

A synthesis of 2-aminopyridines from pyridine N-oxides via their corresponding N-(2-pyridyl)pyridinium salts has been demonstrated and investigated. The reaction sequence features a highly regioselective conversion of the N-oxide into its pyridinium salt

Ruthenium-Catalyzed Reductive Arylation of N-(2-Pyridinyl)amides with Isopropanol and Arylboronate Esters

A new three-component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2-pyridinyl (Py) directing group, is described. The N-Py-amide substrates are readily prepared from carboxylic acids and PyNH2, and the resulting N-Py-1-arylalkanamine reaction products are easily transformed into the corresponding chlorides by substitution of the HN-Py group with HCl. The 1-aryl-1-chloroalkane products allow substitution and cross-coupling reactions. Therefore, a general protocol for the transformation of carboxylic acids into a variety of functionalities is obtained. The Py-NH2 by-product can be recycled.

Synthetic method of 2-amino-5-methyl pyridine

The invention provides a synthetic method of 2-amino-5-methyl pyridine and relates to the field of research and development of chemical synthesis of drugs. The synthetic method comprises the following steps: adding methyl groups to pyridine to prepare 5-methyl pyridine; preparing N-oxidative methyl pyridine by 5-methyl pyridine; preparing 2-nitro-5-methyl nitrogen-oxidative pyridine by nitrogen-oxidative pyridine; and preparing the 2-amino-5-methyl pyridine by the 2-nitro-5-methyl nitrogen-oxidative pyridine. The synthetic method provided by the invention has the advantages of high product yield and purity, low in production cost and good in environment-friendly effect.