4-(((Benzyloxy)carbonyl)amino)benzoic acid

Name: 4-(((Benzyloxy)carbonyl)amino)benzoic acid
Brand: ChemScene
Availability: InStock
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CAS No. 5330-71-2
Cat. No. CS-0453337
Purity≥98%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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4-(((Benzyloxy)carbonyl)amino)benzoic acid|CS-0453337

Structure of 5330-71-2

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General Information

CAS No. 5330-71-2
Cat. No. CS-0453337
Purity ≥98%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₁₃NO₄
Molecular Weight 271.27
Synonym(s) Benzoic acid, 4-[[(phenylmethoxy)carbonyl]amino]- (9CI)
SMILES C1=CC=C(C=C1)COC(=O)NC2=CC=C(C=C2)C(=O)O

Description

4-(((Benzyloxy)carbonyl)amino)benzoic acid features a benzyl-protected amino group flanked by a para-carboxylic acid, enabling selective deprotection in peptide synthesis. This dual-functional scaffold integrates seamlessly into orthogonal protection strategies, offering stable handling and precise coupling control under standard conditions.

Application

4-(((Benzyloxy)carbonyl)amino)benzoic acid serves as a versatile protected amino acid building block, enabling efficient peptide synthesis through orthogonal protection of both amine and carboxylic acid functionalities. The benzyloxycarbonyl (Z) group offers excellent stability under standard reaction conditions and can be selectively removed via hydrogenolysis, facilitating downstream functionalization. Its compatibility with diverse coupling protocols and ease of purification make it a practical choice for multi-step synthetic sequences in medicinal chemistry and API development.

Synthesis

Route1
- 150-13-0
- 501-53-1
- ~95%
- In-stock
  
  5330-71-2
References
- Vernall, Andrea J.; Stoddart, Leigh A.; Briddon, Stephen J.; Hill, Stephen J.; Kellam, Barrie Journal of Medicinal Chemistry, 2012 , vol. 55, # 4 p. 1771 - 1782
Route2
- In-stock
  
  13139-17-8
- 150-13-0
- ~81%
- In-stock
  
  5330-71-2
References
- Ikawa, Takashi; Sajiki, Hironao; Hirota, Kosaku Tetrahedron, 2005 , vol. 61, # 8 p. 2217 - 2231

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P501

Quality Control

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Computational Chemistry Data

TPSA 75.63
LogP 3.1335
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 4

Other Classifications

Building Blocks Functional Group Carboxylic Acid

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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4-(((Benzyloxy)carbonyl)amino)benzoic acid

CAS No. 5330-71-2

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