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

  • CAS No. 262433-02-3

  • Cat. No. CS-0168737
  • Purity≥97%
  • MDL No.None

*For research and further manufacturing use only, not for direct human use.

tert-Butyl (2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate|CS-0168737

Structure of 262433-02-3

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General Information

  • CAS No. 262433-02-3
  • Cat. No. CS-0168737
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₂₈BNO₅
  • Molecular Weight 349.23
  • Synonym(s) 4-(TERT-BUTOXYCARBONYLAMINO)-3-METHOXYPHENYLBORONIC ACID, PINACOL ESTER
  • SMILES O=C(OC(C)(C)C)NC1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1OC

Description

tert-Butyl (2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate delivers a boronate handle flanked by a methoxy group and a bench-stable carbamate protecting group. This arylboron reagent integrates readily into Suzuki-Miyaura coupling reactions under standard conditions, enabling efficient construction of biaryl scaffolds with high functional group tolerance.

Application

tert-Butyl (2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate serves as a stable, bench-friendly boron building block for Suzuki-Miyaura cross-coupling reactions. The protected amine and methoxy group offer orthogonal functionality, enabling sequential transformations in complex molecule synthesis. Its high tolerance to diverse reaction conditions facilitates efficient C–C bond formation with aryl and vinyl halides, making it a practical reagent for constructing biaryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • CALDERWOOD, DAVID; ARNOLD, LEE; MAZDIYASNI, HORMOZ; HIRST, GAVIN C.; DENG, BOJUAN B.; JOHNSTON, DAVID N.; RAFFERTY, PAUL; TOMETZKI, GERALD B.; TWIGGER, HELEN L.; MUNSCHAUER, RAINER Patent: US2003/187001 A1, 2003 ; US 20030187001 A1
  • Route2

    References

    • Kressierer, Christoph J.; Lehnemann, Bernd; Jung, Jorg Patent: US2008/269523 A1, 2008 ; Location in patent: Page/Page column 6-7 ;

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   66.02
  • LogP   3.3414
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   3

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