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ChemicalBook > Product Catalog >Biochemical Engineering >Amino Acids and Derivatives >Amino acid esters >tert-Butyl 4-aminobenzoate

tert-Butyl 4-aminobenzoate

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CAS:18144-47-3
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tert-Butyl 4-aminobenzoate manufacturers

tert-Butyl 4-aminobenzoate Basic information
Product Name:tert-Butyl 4-aminobenzoate
Synonyms:TERT-BUTYL 4-AMINOBENZOATE;4-AMINOBENZOIC ACID TERT-BUTYL ESTER;BUTTPARK 14\02-67;tert-butyl 4-azanylbenzoate;tert-Butyl 4-aminobe;4-(tert-Butoxycarbonyl)aniline;H-4-Abz-OtBu(Tert-butyl 4-AMinobenzoate);Tert-Butyl p-aMinobenzoate
CAS:18144-47-3
MF:C11H15NO2
MW:193.24
EINECS:629-537-4
Product Categories:API intermediates;Aromatic Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives
Mol File:18144-47-3.mol
tert-Butyl 4-aminobenzoate Structure
tert-Butyl 4-aminobenzoate Chemical Properties
Melting point 108-110 °C
Boiling point 322.4±15.0 °C(Predicted)
density 1.078±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
form powder to crystal
pka2.43±0.10(Predicted)
color White to Light yellow to Light orange
BRN 2803178
CAS DataBase Reference18144-47-3(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
10-34
Hazard Note Irritant
HS Code 29224999
MSDS Information
ProviderLanguage
SigmaAldrich English
tert-Butyl 4-aminobenzoate Usage And Synthesis
Usestert-Butyl 4-aminobenzoate can be used to synthesise structural units for antifolate and a novel liver-targeted coupling of PSN-357, a glycogen phosphorylase inhibitor for the treatment of diabetes. It can also be used in the synthesis of tert-butyl 4-aminobenzoate n-substituted derivatives[1].
reaction suitabilityreaction type: solution phase peptide synthesis
Synthesistert-Butyl 4-aminobenzoate is synthesised using tert-butyl 4-nitrobenzoate as raw material by chemical reaction. The specific synthesis steps are as follows:
Tert-butyl 4-nitrobenzoate (4.75 g, 21.279 mmol) was dissolved in MeOH (200 ml) and added with CAUTION was Pd/C (475 mg, 0.1 equiv. w/w) and the flask evacuated prior to purging with N2, re-evacuation and purging with H2. The mixture was stirred under H2 for 5 hours until complete. The mixture was filtered through celite and evaporated to a white solid (4.11 g, 21.269 mmol, quant.). Rf 0.29 [20% EtOAc in Hexane]. Mp. I l l - 113 0C. 1H NMR (400 MHz, CDCl3) δ 7.79 (2H, dt, J=8.6, 2.3 Hz, 2ArH), 6.61 (2H, dt, J=8.6, 2.3 Hz, 2ArH), 4.00 (2H, br s, NH2), 1.56 (9H, s, C(CH3)3) ppm. 13C NMR (100 MHz, CDCl3) δ 165.9 (C=O), 150.4 (ArC), 131.3 (ArCH), 121.7 (ArC), 113.7 (ArCH), 80.0 (C(CH3)3), 28.3 (C(CH3)3) ppm. IR (neat) υmax 3415, 3345, 3235, 2972, 1682, 1598, 1367, 1287, 1154, 1115 cm 1. HRMS mJz calc. C11H15NO2 [M+l] 194.1176, found [M+l] 194.1179.
tert-Butyl 4-aminobenzoate synthesis
References[1] V. BAVETSIAS  E. H. Synthesis of N-substituted derivatives of tert-butyl 4-aminobenzoate via a palladium-catalysed reaction[J]. Journal of Chemical Research-s, 2000. DOI:10.3184/030823400103168100.
tert-Butyl 4-aminobenzoate Preparation Products And Raw materials
Raw materialsTERT-BUTYL-4-BROMOBENZOATE
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