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

Name: tert-Butyl (2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate
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CAS No. 508223-54-9
Cat. No. CS-0136577
Molecule weight333.23
Purity≥97%
MDL No.MFCD17214290

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tert-Butyl (2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate|CS-0136577

Structure of 508223-54-9

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General Information

CAS No. 508223-54-9
Cat. No. CS-0136577
Purity ≥97%
MDL No. MFCD17214290
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₈H₂₈BNO₄
Molecular Weight 333.23
Synonym(s) tert-Butyl 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate
SMILES CC1=CC(B(O2)OC(C)(C)C2(C)C)=CC=C1NC(OC(C)(C)C)=O

Description

This boronate ester features a tert-butyl carbamate-protected arylborane scaffold, enabling stable, room-temperature handling and efficient Suzuki-Miyaura cross-coupling under standard conditions. The tetramethyl-1,3,2-dioxaborolane moiety enhances reactivity while maintaining bench stability, facilitating direct incorporation into complex molecular architectures without preactivation.

Application

tert-Butyl (2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. Its ortho-methyl group provides steric and electronic modulation, while the Boc-protected amine enables selective functionalization and orthogonal deprotection. The tetramethyl-substituted dioxaborolane enhances stability and reactivity in diverse coupling conditions, facilitating efficient construction of biaryl and heterocyclic scaffolds in medicinal chemistry and process development workflows.

Synthesis

Route1
- In-stock
  
  666746-27-6
- 25015-63-8
- ~%
- In-stock
  
  508223-54-9
References
- BAYER CROPSCIENCE AG Patent: WO2006/133823 A1, 2006 ; Location in patent: Page/Page column 68 ;

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-P280-P304+P340-P405

Quality Control

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Computational Chemistry Data

TPSA 56.79
LogP 3.64122
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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

CAS No. 508223-54-9

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