2-IODOBENZYLAMINE Chemical Properties

Melting point:

63-65 °C

Boiling point:

270.0±15.0 °C(Predicted)

Density 

1.772±0.06 g/cm3(Predicted)

storage temp. 

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

pka

8.54±0.10(Predicted)

Appearance

Light yellow to brown Liquid

2-IODOBENZYLAMINE Usage And Synthesis

Synthesis

Triphenylphosphine (6.8 g, 25.7 mmol) was added to an anhydrous tetrahydrofuran (THF, 100 mL) solution of 1-azidomethyl-2-iodobenzene (6.1 g, 23.4 mmol) at 0 °C. The reaction mixture was slowly warmed to room temperature and stirred for 16 hours. After the reaction was completed, the reaction mixture was diluted with ammonium hydroxide (20 mL) and stirring was continued for 3 hours. Subsequently, the reaction mixture was treated with 2M sodium hydroxide solution (30 mL) and stirred for another 1 hour. The reaction mixture was acidified to pH 2 with 3M hydrochloric acid, then diluted with ether and the layers were separated. The aqueous layer was alkalized to pH 9 with 2M sodium hydroxide solution and subsequently extracted with dichloromethane (3 times). The organic phases were combined, dried with anhydrous sodium sulfate and concentrated under vacuum to give an oily residue. The residue was treated with ether and filtered. The filtrate was purified by silica gel column chromatography using 95:5 dichloromethane:methanol as eluent to give 5.4 g (80% yield) of 2-iodobenzylamine.

References

[1] Patent: US2006/25433, 2006, A1. Location in patent: Page/Page column 107
[2] Tetrahedron, 2001, vol. 57, # 48, p. 9697 - 9710
[3] Angewandte Chemie - International Edition, 2005, vol. 44, # 35, p. 5679 - 5682
[4] Patent: US2006/24834, 2006, A1. Location in patent: Page/Page column 5-6; Sheet 7
[5] Journal of Organic Chemistry, 2010, vol. 75, # 24, p. 8410 - 8415

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