2-Amino-5-methylpyridine CAS 1603-41-4

Introduction：Basic information about 2-Amino-5-methylpyridine CAS 1603-41-4, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

2-Amino-5-methylpyridine Basic information

• Product Name: 2-Amino-5-methylpyridine
• Synonyms: 5-Methyl-2-aminopyridine;5-methyl-2-pyridinamin;5-Methyl-2-pyridinamine;5-Methyl-2-pyridylamine dine;6-Amino-3-picoline 2-Amino-5-picoline5-Methyl-2-pyridylamine;6-Amino-3-picoline, 5-Methylpyridin-2-amine;2-AMino-5-picoline, 99% 10GR;6-amino-3-picolin
• CAS: 1603-41-4
• MF: C6H8N2
• MW: 108.14
• EINECS: 216-503-5
• Product Categories: Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Heterocycle-Pyridine series;amine;Aromatics;Heterocycles;Pyridine series;Pyridine;Pyridines, Pyrimidines, Purines and Pteredines;VARIOUSAMINE;Amines;Pyridines;Pyridines derivates;bc0001;C6
• Mol File: 1603-41-4.mol

2-Amino-5-methylpyridine Chemical Properties

• Melting point: 76-77 °C(lit.)
• Boiling point: 227 °C(lit.)
• density: 227
• vapor pressure: 3.706Pa at 25℃
• refractive index: 1,524-1,528
• Fp: 118°C
• storage temp.: Keep in dark place,Inert atmosphere,Room temperature
• solubility: 1000g/l
• form: Crystalline Powder, Crystals or Flakes
• pka: pK1: 7.22(+1) (25°C)
• color: White to light yellow
• Sensitive: Hygroscopic
• BRN: 107050
• InChI: 1S/C6H8N2/c1-5-2-3-6(7)8-4-5/h2-4H,1H3,(H2,7,8)
• InChIKey: CMBSSVKZOPZBKW-UHFFFAOYSA-N
• SMILES: Cc1ccc(N)nc1
• LogP: 1.08
• CAS DataBase Reference: 1603-41-4(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyridinamine, 5-methyl-(1603-41-4)
• EPA Substance Registry System: 6-Amino-3-picoline (1603-41-4)

Safety Information

• Hazard Codes: T,Xi
• Risk 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
• Hazard Note: Irritant
• TSCA: TSCA listed
• HazardClass: 6.1
• PackingGroup: III
• HS Code: 29333999
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
• Hazard Classifications: Acute Tox. 3 Dermal Acute Tox. 3 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3
• Toxicity: LD50 orl-rat: 200 mg/kg 85JCAE -,841,86

2-Amino-5-methylpyridine Usage And Synthesis

Chemical Properties

light yellow crystalline flakes

Uses

2-Amino-5-methylpyridine is used as an intermediate in the pharmaceutical industry for the manufacture of Avosentan (used in diabetic nephropathy), Pirfenidone (anti-inflammatory, anti-oxidant and antifibrotic agent) and Zolpidem (sedative/ hypnotics). It is also used for the manufacture of Fluazuron, which is a pesticide, and for commercial purposes.

Production Methods

2-Amino-5-methylpyridine is obtained when 3-methyl-pyridine is reacted with sodium amide in an inert diluent at elevated temperature and elevated pressure (compare U.S. Pat. No. 4,386,209).

Safety Profile

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

Synthesis

2.2 g (0.377 mol) of trimethylamine are condensed at -10 °C. and added at -5 °C. to a solution of 10.03 g (0.092 mol) of 3-methyl-pyridine 1-oxide in 120 ml of methylene chloride. At this temperature, 7.9 (0.11 mol) of thionyl chloride in 15 ml of methylene chloride is added dropwise in 30 minutes. The temperature during this process is kept below 0 °C. The resulting yellow solution is allowed to thaw and is stirred overnight at room temperature. The solvent is removed in vacuo 35 ml of a 48% strength hydrogen bromide solution and then added. The water is distilled off, and the mixture is then heated to 210 °C. A 48% strength hydrogen bromide solution is continuously added dropwise, and water is distilled. After 8 hours, the reaction is completed according to thin-layer chromatography. The mixture is allowed to cool and is adjusted to pH 9 using a dilute sodium hydroxide solution. The mixture is then extracted four times using ethyl acetate. After filtration, the combined extracts are dried over sodium sulphate and concentrated on the rotary evaporator. 8 g (80.5% of theory) of 2-amino-5-methylpyridine are obtained.

Purification Methods

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

References

[1] Catalysis Communications, 2013, vol. 32, p. 28 - 31
[2] Advanced Synthesis and Catalysis, 2009, vol. 351, # 11-12, p. 1722 - 1726

2-Amino-5-methylpyridine Preparation Products And Raw materials

• Raw materials: Hydrogen bromide-->Trimethylamine-->Chloromethane-->Trimethylamine hydrochloride-->3-Picoline-N-oxide-->5-Methylpyridine-->3-Picoline-->2-Bromo-5-methylpyridine-->Ammonia-->Cesium carbonate
• Preparation Products: 2-Chloro-5-methylpyridine-->Ethyl 6-aminonicotinate-->(5-METHOXYMETHYL-PYRIDIN-2-YL)-CARBAMIC ACID TERT-BUTYL ESTER-->6-(2,2,2-TRIFLUOROETHOXY)NICOTINIC ACID-->3-AMINO-2-CHLORO-5-PICOLINE-->6-Aminonicotinic acid-->(6-AMINO-3-PYRIDINYL)METHANOL-->TERT-BUTYL [5-(HYDROXYMETHYL)PYRIDIN-2-YL]CARBAMATE-->6-CHLOROPYRIDINE-3,4-DICARBOXYLIC ACID-->METHYL 6-[(TERT-BUTOXYCARBONYL)AMINO]NICOTINATE-->Methyl 6-aminonicotinate-->Nalidixic acid-->2-Chloro-5-methyl-3-nitropyridine-->6-AMINONICOTINOHYDRAZIDE-->2-BROMO-3-NITRO-5-METHYL PYRIDINE-->2,3-Dichloro-5-(trifluoromethyl)pyridine-->2-Amino-3-bromo-5-methylpyridine-->2-Hydroxy-5-methyl-3-nitropyridine-->2-FLUOROPYRIDINE-5-CARBONYL CHLORIDE-->METHYL 6-(ACETYLAMINO)NICOTINATE-->6-Fluoronicotinic acid-->2-ACETYLAMINO-3-BROMO-5-METHYLPYRIDINE-->2-ACETAMIDO-5-PYRIDINECARBOXYLIC ACID-->2-AMINO-3-NITRO-5-PICOLINE-->2-Fluoro-5-methylpyridine-->2-ACETAMIDO-5-PICOLINE