tert-Butyl 4-bromobenzylcarbamate

Name: tert-Butyl 4-bromobenzylcarbamate
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CAS No. 68819-84-1
Cat. No. CS-W005364
Purity≥96%
MDL No.None

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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-bromobenzylcarbamate|CS-W005364

Structure of 68819-84-1

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General Information

CAS No. 68819-84-1
Cat. No. CS-W005364
Purity ≥96%
MDL No. None
Storage RT, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₆BrNO₂
Molecular Weight 286.16
Synonym(s) tert-Butyl N-(4-bromobenzyl)carbamate
SMILES O=C(OC(C)(C)C)NCC1=CC=C(Br)C=C1

Description

tert-Butyl 4-bromobenzylcarbamate features a brominated benzyl group attached to a carbamate moiety, enabling direct incorporation into Suzuki-Miyaura coupling reactions. The tert-butyl carbamate serves as a robust amine-protecting group, stable under a range of reaction conditions and readily removed via acidolysis. This compound facilitates the synthesis of functionalized anilines with high chemoselectivity and minimal side-product formation.

Application

tert-Butyl 4-bromobenzylcarbamate serves as a robust protecting group for primary amines, enabling selective functionalization in multi-step syntheses. The bromobenzyl moiety provides a versatile handle for subsequent cross-coupling reactions, including Suzuki and Stille couplings. Its stability under diverse reaction conditions and ease of removal via acidolysis make it ideal for iterative synthesis workflows.

Synthesis

Route1
- In-stock
  
  24424-99-5
- In-stock
  
  26177-44-6
- ~97%
- In-stock
  
  68819-84-1
References
- EP1056733 B1, ; Page 26 ;
Route2
- In-stock
  
  24424-99-5
- In-stock
  
  3959-07-7
- ~99%
- In-stock
  
  68819-84-1
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 13, # 20 p. 3557 - 3560
Route3
- 1228692-99-6
- ~90%
- In-stock
  
  68819-84-1
References
- Chemistry - A European Journal, , vol. 16, # 15 p. 4557 - 4566

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 38.33
LogP 3.4738
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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tert-Butyl 4-bromobenzylcarbamate

CAS No. 68819-84-1

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