tert-Butyl benzyloxycarbamate

Name: tert-Butyl benzyloxycarbamate
Brand: ChemScene
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CAS No. 79722-21-7
Cat. No. CS-W001647
Molecule weight223.27
Purity≥97%
MDL No.MFCD00191873

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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+
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tert-Butyl benzyloxycarbamate|CS-W001647

Structure of 79722-21-7

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General Information

CAS No. 79722-21-7
Cat. No. CS-W001647
Purity ≥97%
MDL No. MFCD00191873
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₇NO₃
Molecular Weight 223.27
Synonym(s) tert-Butyl N-(benzyloxy)carbamate
SMILES O=C(OC(C)(C)C)NOCc1ccccc1

Description

tert-Butyl benzyloxycarbamate serves as a robust, bench-stable N-terminal protecting group in peptide synthesis. This carbamate derivative combines the stability of the tert-butyl moiety with the orthogonal cleavability of the benzyl ether, enabling selective deprotection under mild hydrogenation conditions. The protected nitrogen remains inert under standard coupling protocols, facilitating efficient chain elongation.

Application

tert-Butyl benzyloxycarbamate serves as a robust, bench-stable amine protecting group that enables selective N-alkylation and peptide coupling reactions. Its stability under diverse reaction conditions facilitates orthogonal deprotection strategies, particularly via hydrogenolysis or acidic cleavage. The compound functions effectively in the synthesis of complex heterocycles and bioactive intermediates, offering reliable handling and straightforward purification.

Synthesis

Route1
- In-stock
  
  24424-99-5
- In-stock
  
  2687-43-6
- ~97%
- In-stock
  
  79722-21-7
References
- Bongim; Cardillo; Gentilucci; Tomasini Journal of Organic Chemistry, 1997 , vol. 62, # 26 p. 9148 - 9159
Route2
- 622-33-3
- In-stock
  
  24424-99-5
- ~10%
- In-stock
  
  79722-21-7
References
- INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM); GUICHOU, Jean-Francois; COLLIANDRE, Lionel; AHMED-BELKACEM, Hakim; PAWLOTSKY, Jean-Michel Patent: WO2011/76784 A2, 2011 ; Location in patent: Page/Page column 96-97 ;
Route3
- In-stock
  
  34619-03-9
- In-stock
  
  2687-43-6
- ~91%
- In-stock
  
  79722-21-7
References
- Kadi, Nadia; Arbache, Simon; Song, Lijiang; Oves-Costales, Daniel; Challis, Gregory L. Journal of the American Chemical Society, 2008 , vol. 130, # 32 p. 10458 - 10459

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-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 47.56
LogP 2.6429
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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tert-Butyl benzyloxycarbamate

CAS No. 79722-21-7

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