tert-Butyl N-[4-(aminomethyl)phenyl]carbamate Chemical Properties

Melting point:

64-68 °C(lit.)

Boiling point:

300.1±25.0 °C(Predicted)

Density 

1.120±0.06 g/cm3(Predicted)

storage temp. 

2-8°C, protect from light, stored under nitrogen

form 

solid

pka

13.68±0.70(Predicted)

color 

white

CAS DataBase Reference

220298-96-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,C,Xn

Risk Statements 

36/37/38-34-22-43

Safety Statements 

26-36-45-36/37/39-22-36/37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2922290090

MSDS

• Language:English Provider:SigmaAldrich

tert-Butyl N-[4-(aminomethyl)phenyl]carbamate Usage And Synthesis

Uses

4-(Boc-amino)benzylamine is used in preparation of degradation agents for Cyclin dependent kinase useful for the treatment of cancer.

Synthesis

General procedure for the synthesis of 4-aminomethyl-N-Boc-aniline from N-BOC-4-aminobenzonitrile: 4-(tert-butoxycarbonylamino)benzyl cyanide (1 g, 4.58 mmol) was dissolved in a solvent mixture of THF/isopropanol (1:1, 142 mL) and 10% Pd/C (Degussa type E101, 0.56 g, 0.26 mmol) was added . The reaction system was added via syringe under nitrogen protection. After purging the reaction mixture with nitrogen, it was hydrogenated overnight under 50 psi hydrogen pressure. Upon completion of the reaction, the catalyst was removed by Celite filtration. The filter cake was washed thoroughly with isopropanol (100 mL) and THF (100 mL). The filtrate was concentrated in vacuum and the resulting crude product was purified by silica gel column chromatography and separated using a methanol solution of DCM/2M ammonia (gradient elution procedure: 1:0 to 95:5 for 30 min; 95:5 for 3 min; 95:5 to 9:1 for 30 min; 9:1 for 30 min) to afford the target product, 4-aminomethyl-N-Boc-aniline (0.364 g, 36% yield) . Mass spectrum (ES-) m/z: 220.1 ([M-H]-).

References

[1] Patent: WO2007/28083, 2007, A2. Location in patent: Page/Page column 112

tert-Butyl N-[4-(aminomethyl)phenyl]carbamate(220298-96-4)Related Product Information

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• BUTYL OLEATE
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