4-BROMO-2-METHYLBENZYLAMINE Chemical Properties

Boiling point:

270.9±25.0 °C(Predicted)

Density 

1.410±0.06 g/cm3(Predicted)

storage temp. 

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

pka

9.03±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

Sensitive 

Air Sensitive

InChI

InChI=1S/C8H10BrN/c1-6-4-8(9)3-2-7(6)5-10/h2-4H,5,10H2,1H3

InChIKey

CRDQDMSHRCFAAW-UHFFFAOYSA-N

SMILES

C1(CN)=CC=C(Br)C=C1C

Safety Information

Hazard Codes 

T

4-BROMO-2-METHYLBENZYLAMINE Usage And Synthesis

Synthesis

Under nitrogen protection, 4-bromo-2-methylbenzonitrile (3.0 g, 15 mmol) was dissolved in anhydrous tetrahydrofuran (20 mL) and cooled to 0 °C. A tetrahydrofuran solution (46 mL) of 1.0 M borane was added slowly, keeping the reaction temperature at 0 °C. The reaction mixture was stirred at 0 °C for 1 h before being warmed to 80 °C and heated overnight. Upon completion of the reaction, the mixture was cooled to 0 °C and the reaction was quenched by slow addition of methanol and subsequently concentrated under vacuum. The crude product was treated with ethyl acetate (20 mL) and a 1,4-dioxane solution (8.0 mL, 32 mmol) of 4 M hydrochloric acid for 5 min. The solid was collected by filtration, washed with ether and dried to give 4-bromo-2-methylbenzenemethanamine as a white powder (3.24 g, yield: 100%). Liquid chromatography-mass spectrometry (LCMS) analysis: retention time (RT) 0.75 min, molecular ion peak (MH+) 200.0. nuclear magnetic resonance hydrogen spectrum (1H NMR, 300 MHz, DMSO-d6) δ: 8.28 (broad single peak, 2H), 7.42-7.54 (multiple peaks, 2H), 7.34 (double peak, J = 7.93 Hz, 1H) , 3.99 (double peak, J = 4.15 Hz, 2H), 2.35 (single peak, 3H).

References

[1] Patent: WO2015/89337, 2015, A1. Location in patent: Paragraph 0617
[2] Patent: WO2016/201271, 2016, A1. Location in patent: Paragraph 0114
[3] Patent: WO2015/89327, 2015, A1. Location in patent: Paragraph 0195

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