[2-(4-AMINO-PHENYL)-ETHYL]-CARBAMIC ACID TERT-BUTYL ESTER Chemical Properties

Melting point:

71 - 73°C

Boiling point:

396.8±25.0 °C(Predicted)

Density 

1.077±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

12.81±0.46(Predicted)

color 

Brown

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C13H20N2O2/c1-13(2,3)17-12(16)15-9-8-10-4-6-11(14)7-5-10/h4-7H,8-9,14H2,1-3H3,(H,15,16)

InChIKey

HOPALBZGTWDOTL-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCCC1=CC=C(N)C=C1

Safety Information

RIDADR 

2811

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2921599090

[2-(4-AMINO-PHENYL)-ETHYL]-CARBAMIC ACID TERT-BUTYL ESTER Usage And Synthesis

Uses

4-[2-(Boc-amino)ethyl]aniline is used as a intermediate for chemical research.

Synthesis

General procedure for the synthesis of 4-[2-(Boc-amino)ethyl]aniline from tert-butyl N-[2-(4-nitrophenyl)ethyl]carbamate: To a solution of tert-butyl N-[2-(4-nitrophenyl)ethyl]carbamate (18.7 g, 70.30 mmol) in ethanol (200 ml), a slurry of 10% palladium-carbon (2 g) was added. Water (10 ml) was subsequently added. Anhydrous ammonium formate (44.3 g, 703 mmol) was added to the reaction system at 80°C. Triethylamine (90 ml) was added slowly. After addition, the mixture was stirred at 80 °C for 1 hour. After completion of the reaction, the mixture was allowed to cool to room temperature, filtered and concentrated under vacuum. The residue was diluted with water and extracted twice with dichloromethane. The combined organic layers were washed with water, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure to afford the target product 4-[2-(Boc-amino)ethyl]aniline as a yellow oil (13.5 g, 81% yield).

References

[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5627 - 5631
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 10, p. 2852 - 2855
[3] Patent: WO2008/13997, 2008, A2. Location in patent: Sheet 9
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2845 - 2854
[5] Patent: WO2006/40179, 2006, A1. Location in patent: Page/Page column 99

[2-(4-AMINO-PHENYL)-ETHYL]-CARBAMIC ACID TERT-BUTYL ESTER(94838-59-2)Related Product Information

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• BOC-PHE(4-NO2)-OH DCHA
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• BOC-(R)-3-AMINO-4-(4-NITRO-PHENYL)-BUTYRIC ACID
• Boc-4-Amino-L-phenylalanine
• [2-(3-AMINO-PHENYL)-ETHYL]-CARBAMIC ACID TERT-BUTYL ESTER
• [2-(2-AMINO-PHENYL)-ETHYL]-CARBAMIC ACID TERT-BUTYL ESTER
• BOC-P-AZIDO-PHE-OH
• BOC-PHE(4-NHAC)-OH
• BOC-PHE(3,5-DII,4-NH2)-OH
• BOC-PHE(4-NHFMOC)-OH
• BOC-N-ME-P-NITRO-PHE-OH DCHA