Tert-butyl 4-hydroxybenzylcarbamate

Name: Tert-butyl 4-hydroxybenzylcarbamate
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CAS No. 149505-94-2
Cat. No. CS-0068163
Molecule weight223.27
Purity≥97%
MDL No.MFCD18206146

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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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Tert-butyl 4-hydroxybenzylcarbamate|CS-0068163

Structure of 149505-94-2

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General Information

CAS No. 149505-94-2
Cat. No. CS-0068163
Purity ≥97%
MDL No. MFCD18206146
Storage RT, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₇NO₃
Molecular Weight 223.27
Synonym(s) tert-butyl N-[(4-hydroxyphenyl)methyl]carbonate
SMILES O=C(OC(C)(C)C)NCC1=CC=C(O)C=C1

Description

Tert-butyl 4-hydroxybenzylcarbamate features a phenolic hydroxyl group flanked by a tert-butyl carbamate protecting group, enabling selective deprotection under mild acidic conditions. This combination imparts stability during synthetic manipulations while facilitating precise functionalization in peptide and small-molecule synthesis workflows.

Application

Tert-butyl 4-hydroxybenzylcarbamate serves as a versatile protecting group for primary amines, enabling selective functionalization in complex molecule synthesis. The tert-butyl carbamate moiety offers excellent stability under basic and mildly acidic conditions, while the phenolic hydroxyl group permits orthogonal modifications. It facilitates efficient coupling reactions and is readily cleaved under mild acidic conditions, making it ideal for iterative synthetic sequences in medicinal chemistry and API development.

Safety Information

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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 : P260-P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501

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Computational Chemistry Data

TPSA 58.56
LogP 2.4169
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Phenol

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Tert-butyl 4-hydroxybenzylcarbamate

CAS No. 149505-94-2

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