tert-Butyl 4-aminobenzoate

Name: tert-Butyl 4-aminobenzoate
Brand: ChemScene
Availability: InStock
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CAS No. 18144-47-3
Cat. No. CS-M1336
Purity≥98%
MDL No.MFCD00665790

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Structure of 18144-47-3

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General Information

CAS No. 18144-47-3
Cat. No. CS-M1336
Purity ≥98%
MDL No. MFCD00665790
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₅NO₂
Molecular Weight 193.24
Synonym(s) Tert-butyl-4-amino benzoato
SMILES O=C(C(C=C1)=CC=C1N)OC(C)(C)C

Description

tert-Butyl 4-aminobenzoate features a para-amino group conjugated to an electron-rich aromatic ring, enabling efficient coupling in amide bond formation. The tert-butyl ester moiety provides enhanced solubility and stability under standard conditions, while the primary amine offers direct handle for derivatization. This combination delivers a robust scaffold for peptide synthesis and medicinal chemistry applications.

Application

tert-Butyl 4-aminobenzoate serves as a versatile building block in medicinal chemistry, enabling direct access to substituted anilines and benzamide derivatives. The tert-butyl ester group provides excellent bench stability and facilitates straightforward deprotection under mild acidic conditions. Its para-amino functionality exhibits high tolerance to diverse reaction conditions, supporting subsequent coupling, acylation, and cyclization steps common in API synthesis.

Synthesis

Route1
- In-stock
  
  19756-72-0
- ~97%
- In-stock
  
  18144-47-3
References
- Drewe, William C.; Nanjunda, Rupesh; Gunaratnam, Mekala; Beltran, Monica; Parkinson, Gary N.; Reszka, Anthony P.; Wilson, W. David; Neidle, Stephen Journal of Medicinal Chemistry, 2008 , vol. 51, # 24 p. 7751 - 7767
Route2
- 150-13-0
- ~64%
- In-stock
  
  18144-47-3
References
- BEECHAM GROUP PLC Patent: EP283563 B1, 1991 ;
Route3
- In-stock
  
  59247-47-1
- ~0%
- In-stock
  
  18144-47-3
- 150-13-0
References
- Weigand, Klaus; Pelka, Sylvie Organic Letters, 2002 , vol. 4, # 26 p. 4689 - 4692

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 52.32
LogP 2.2241
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Peptide Chemistry Unnatural Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Peptide Chemistry Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Peptide Chemistry Unnatural Amino Acid Derivatives

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tert-Butyl 4-aminobenzoate

CAS No. 18144-47-3

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