tert-Butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)carbamate

Name: tert-Butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)carbamate
Brand: ChemScene
Availability: InStock
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CAS No. 1032528-06-5
Cat. No. CS-0040967
Purity≥97%
MDL No.MFCD18762017

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tert-Butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)carbamate|CS-0040967

Structure of 1032528-06-5

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General Information

CAS No. 1032528-06-5
Cat. No. CS-0040967
Purity ≥97%
MDL No. MFCD18762017
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₁H₃₂BNO₄
Molecular Weight 373.29
Synonym(s) tert-Butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxabo-rolan-2-yl)phenyl)cyclobutyl)carbamate
SMILES O=C(OC(C)(C)C)NC1(C2=CC=C(B3OC(C)(C)C(C)(C)O3)C=C2)CCC1

Description

This tert-butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)carbamate integrates a boronate handle with a sterically hindered cyclobutyl scaffold, enabling robust Suzuki-Miyaura coupling under standard conditions. The protecting group remains stable during reaction setup and is readily removed post-functionalization, streamlining access to complex biaryl architectures.

Application

tert-Butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)carbamate serves as a robust boronate building block for Suzuki-Miyaura cross-coupling reactions. The cyclobutyl scaffold imparts conformational rigidity, enhancing stereochemical control in target molecule synthesis. The Bpin group enables high functional group tolerance and reliable coupling under mild conditions, while the tert-butyl carbamate offers stability and straightforward deprotection. This reagent facilitates efficient access to complex arylated cyclobutane motifs common in medicinal chemistry and agrochemical research.

Synthesis

Route1
- In-stock
  
  1032350-06-3
- In-stock
  
  73183-34-3
- ~90%
- In-stock
  
  1032528-06-5
References
- WO2013/104611 A1, ; Page/Page column 48 ;
Route2
- 1032349-96-4
- In-stock
  
  73183-34-3
- ~%
- In-stock
  
  1032528-06-5
References
- US2008/161317 A1, ; Page/Page column 71-72 ;
Route3
- In-stock
  
  24424-99-5
- ~%
- In-stock
  
  1032528-06-5
References
- WO2012/7345 A2, ; WO 2012/007345 A2

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 56.79
LogP 3.8897
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Fatty ring compounds Cyclobutane compounds

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tert-Butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)carbamate

CAS No. 1032528-06-5

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