Tert-butyl 4-cyanobenzylcarbamate

Name: Tert-butyl 4-cyanobenzylcarbamate
Brand: ChemScene
Availability: InStock
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CAS No. 66389-80-8
Cat. No. CS-0068032
Purity≥98%
MDL No.MFCD08436197

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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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Tert-butyl 4-cyanobenzylcarbamate|CS-0068032

Structure of 66389-80-8

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General Information

CAS No. 66389-80-8
Cat. No. CS-0068032
Purity ≥98%
MDL No. MFCD08436197
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₆N₂O₂
Molecular Weight 232.28
Synonym(s) Carbamicacid, [(4-cyanophenyl)methyl]-, 1,1-dimethylethyl ester
SMILES O=C(OC(C)(C)C)NCC1=CC=C(C#N)C=C1

Description

Tert-butyl 4-cyanobenzylcarbamate serves as a stable, bench-ready protecting group for primary amines in synthetic workflows. The carbamate moiety enables selective deprotection under mild acidic conditions, while the para-cyano substituent imparts enhanced electron-withdrawing character, improving reactivity in coupling reactions. This compound integrates seamlessly into peptide and small-molecule synthesis sequences.

Application

Tert-butyl 4-cyanobenzylcarbamate serves as a versatile protected amine building block in synthetic organic chemistry. The tert-butyl carbamate (Boc) group enables mild, orthogonal deprotection under acidic conditions, while the para-cyano functionality offers a handle for further functionalization via nucleophilic addition or reduction. Its stability under diverse reaction conditions facilitates use in peptide synthesis and heterocyclic scaffold construction, particularly in the development of biologically active compounds requiring precise nitrogen protection and strategic cyanide reactivity.

Synthesis

Route1
- In-stock
  
  24424-99-5
- ~95%
- In-stock
  
  66389-80-8
References
- ASTRAZENECA AB; ASTRAZENECA UK LIMITED Patent: WO2006/90153 A1, 2006 ; Location in patent: Page/Page column 15-16 ;
Route2
- In-stock
  
  24424-99-5
- In-stock
  
  15996-76-6
- ~99%
- In-stock
  
  66389-80-8
References
- Willems, Lianne I.; Li, Nan; Florea, Bogdan I.; Ruben, Mark; Van Der Marel, Gijsbert A.; Overkleeft, Herman S. Angewandte Chemie - International Edition, 2012 , vol. 51, # 18 p. 4431 - 4434
Route3
- In-stock
  
  24424-99-5
- In-stock
  
  10406-25-4
- ~96%
- In-stock
  
  66389-80-8
References
- Mok, N. Yi; Chadwick, James; Kellett, Katherine A. B.; Casas-Arce, Eva; Hooper, Nigel M.; Johnson, A. Peter; Fishwick, Colin W. G. Journal of Medicinal Chemistry, 2013 , vol. 56, # 5 p. 1843 - 1852

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

Quality Control

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Computational Chemistry Data

TPSA 62.12
LogP 2.58298
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Cyanide/Nitrile

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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Tert-butyl 4-cyanobenzylcarbamate

CAS No. 66389-80-8

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