Tert-butyl 4-cyanobenzylcarbamate

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

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Type	HazMat Fee
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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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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.

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

Computational Chemistry Data

TPSA 62.12
LogP 2.58298
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

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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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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