3-iodo-5-(trifluoromethyl)-2-pyridinylamine Chemical Properties

Melting point:

97-98°

Boiling point:

269.4±40.0 °C(Predicted)

Density 

2.049±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

2.15±0.49(Predicted)

Appearance

Off-white to light yellow Solid

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

3-iodo-5-(trifluoromethyl)-2-pyridinylamine Usage And Synthesis

Synthesis

Concentrated sulfuric acid (5 mL), periodate (26 g, 123 mmol) and iodine (62 g, 246 mmol) were sequentially added to a stirred solution of 5-(trifluoromethyl)pyridin-2-amine (100 g, 617 mmol) in acetic acid (1 L) under argon protection and at room temperature. The reaction mixture was heated to 80 °C and stirred continuously for 16 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the complete consumption of the raw materials, the reaction mixture was cooled to 0 °C and alkalized with sodium hydroxide solution (200 mL) to precipitate the solid product. The solid was collected by filtration and concentrated under vacuum to afford the target compound 3-iodo-5-(trifluoromethyl)pyridin-2-amine (120 g, 67% yield) as an off-white solid. The product was characterized by 1H NMR (DMSO-d6, 500 MHz): δ 8.27 (s, 1H), 8.16 (s, 1H), 6.87 (brs, 2H); TLC conditions: 10% ethyl acetate/hexane (Rf 0.4).

References

[1] Patent: WO2008/79346, 2008, A1. Location in patent: Page/Page column 58
[2] Patent: WO2017/31325, 2017, A1. Location in patent: Paragraph 0522
[3] Patent: WO2017/133667, 2017, A1. Location in patent: Page/Page column 116; 117
[4] Journal of Medicinal Chemistry, 2013, vol. 56, # 3, p. 1160 - 1170
[5] Patent: US2005/277681, 2005, A1. Location in patent: Page/Page column 26

3-iodo-5-(trifluoromethyl)-2-pyridinylamine(211308-82-6)Related Product Information

• 3-Iodo-5-(trifluoromethyl)-2(1H)-pyridinone
• 2-Amino-3-bromo-5-methylpyridine
• 2-Amino-3-bromo-5-(trifluoromethyl)-pyridine
• 2-Amino-3-bromo-5-nitropyridine
• METHYL 6-AMINO-5-BROMONICOTINATE
• 6-AMino-5-iodo-nicotinic acid Methyl ester
• methyl 6-amino-5-chloronicotinate
• 2-AMINO-3-IODO-5-NITROPYRIDINE
• 3-Chloro-5-(trifluoromethyl)pyridin-2-amine
• 6-AMINO-5-CHLORO-NICOTINONITRILE
• 2-AMINO-3-CHLORO-5-NITROPYRIDINE
• 2-AMINO-3-IODO-5-METHYLPYRIDINE
• 3-iodo-5-(trifluoromethyl)-2-pyridinylamine
• 5-(Trifluoromethyl)pyridin-2-amine