5-IODO-4-METHYL-PYRIDIN-2-YLAMINE Chemical Properties

Melting point:

117.3-118.0°C

Boiling point:

307.7±42.0 °C(Predicted)

Density 

1.898±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

form 

powder to crystal

pka

5.53±0.24(Predicted)

color 

Light yellow to Brown to Dark green

Sensitive 

Light Sensitive

InChIKey

HYRZCIXFHXERJT-UHFFFAOYSA-N

CAS DataBase Reference

356561-08-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-41

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

5-IODO-4-METHYL-PYRIDIN-2-YLAMINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-amino-5-iodo-4-methylpyridine from 2-amino-4-methylpyridine: To a stirred solution of 2-amino-4-methylpyridine (30 g, 278 mmol, 1.0 eq.) in acetic acid (167 mL) was added sequentially periodate (12.7 g, 55.6 mmol, 0.2 eq.), sulfuric acid (4.8 mL, 90.8 mmol, 0.34 equiv), water (33.3 mL) and iodine (28.7 g, 111.1 mmol, 0.4 equiv). The reaction mixture was heated and stirred at 80 °C for 6 h. After the completion of the reaction was monitored by TLC, the mixture was cooled to room temperature and slowly poured into sodium thiosulfate solution (200 mL) to precipitate a red oily substance. After separation of the oily material, the aqueous phase was alkalized with 50% sodium hydroxide solution (100 mL) and a yellow solid was precipitated. The solid was extracted with ether (2 x 200 mL), the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure to give a brown semi-solid crude product (60 g). The crude product was purified by column chromatography on silica gel (100-200 mesh), and the fraction containing the target compound was collected by using hexane solution of 15% ethyl acetate as eluent and concentrated under reduced pressure to give 2-amino-5-iodo-4-methylpyridine as a light brown solid (50.7 g, 78% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 2.27 (s, 3H), 4.46 (bs, 2H), 6.44 (s, 1H), 8.24 (s, 1H).

References

[1] Patent: WO2014/39484, 2014, A1. Location in patent: Page/Page column 60
[2] Tetrahedron Letters, 2001, vol. 42, # 23, p. 3795 - 3797
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 25, p. 6383 - 6391
[4] Tetrahedron Letters, 2003, vol. 44, # 14, p. 2971 - 2973
[5] Synlett, 2012, # 2, p. 208 - 214

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