4-(Boc-aminomethyl)aniline Chemical Properties

Melting point:

75-78 °C(lit.)

Boiling point:

382.3±25.0 °C(Predicted)

Density 

1.095±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

12.62±0.46(Predicted)

form 

Crystalline Powder

color 

White to tan

InChI

InChI=1S/C12H18N2O2/c1-12(2,3)16-11(15)14-8-9-4-6-10(13)7-5-9/h4-7H,8,13H2,1-3H3,(H,14,15)

InChIKey

UXWQXBSQQHAGMG-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCC1=CC=C(N)C=C1

CAS DataBase Reference

94838-55-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29242990

4-(Boc-aminomethyl)aniline Usage And Synthesis

Chemical Properties

White solid

Uses

4-[(N-Boc)aminomethyl]aniline may be used in the synthesis of haptens and 4-(N-boc-aminomethyl)benzene diazonium tetrafluoroborate salt.

Uses

An aniline derivative, 4-(Boc-aminomethyl)aniline can be used in the preparation of various organic synthase inhibitors and other bio-active compounds.

General Description

4-[(N-Boc)aminomethyl]aniline is a protected amine.

Synthesis

General procedure for the synthesis of 4-(N-BOC-aminomethyl)aniline from N-Boc-4-nitrophenylethylamine: 10% Pd/C catalyst (62 mg) was added to a solution of N-Boc-4-nitrophenylethylamine (590 mg, 2.33 mmol) in methanol (20.6 mL). The reaction mixture was subjected to hydrogenation under 35 psi hydrogen pressure for 2 hours at room temperature. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was evaporated. The residue was purified by silica gel column chromatography using ethyl acetate with hexane (1:1) as eluent to afford 4-(N-BOC-aminomethyl)aniline (520 mg, 100% yield) as an oil.1H NMR (DMSO-d6): δ 1.37 (s, 9H), 3.91 (d, J=6.0 Hz, 2H), 4.90 (s, 2H disappeared after D2O exchange), 6.47 (d, J=8.1Hz, 2H), 6.87 (d, J=8.0Hz, 2H), 7.13ppm (s, 1H, disappeared after D2O exchange).IR: ν1695, 2974 cm-1.

References

[1] European Journal of Medicinal Chemistry, 2014, vol. 80, p. 101 - 111
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 5, p. 691 - 701
[3] Patent: US2009/54395, 2009, A1. Location in patent: Page/Page column 48
[4] Chemical Communications, 2014, vol. 50, # 97, p. 15305 - 15308
[5] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 6, p. 553 - 557

4-(Boc-aminomethyl)aniline(94838-55-8)Related Product Information

• 3-(BOC-AMINOMETHYL)ANILINE