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Methyl 3-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

  • CAS No. 850689-27-9

  • Cat. No. CS-0041210
  • Molecule weight277.12
  • Purity≥97%
  • MDL No.MFCD09258776

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

Methyl 3-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate|CS-0041210

Structure of 850689-27-9

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General Information

  • CAS No. 850689-27-9
  • Cat. No. CS-0041210
  • Purity ≥97%
  • MDL No. MFCD09258776
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₂₀BNO₄
  • Molecular Weight 277.12
  • Synonym(s) Methyl 3-Amino-5-boronobenzoate, pinacol ester
  • SMILES COC(=O)C1=CC(N)=CC(=C1)B1OC(C)(C)C(C)(C)O1

Description

Methyl 3-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate features a boronate ester group enabling reliable Suzuki-Miyaura cross-coupling under standard conditions. The para-amino substituent offers enhanced reactivity and directs regioselective functionalization. This bench-stable reagent integrates seamlessly into complex molecular architectures requiring nitrogenated heterocyclic motifs.

Application

Methyl 3-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group enables efficient coupling under mild conditions, while the ortho-amino and ester functionalities offer orthogonal reactivity for downstream modifications. Bench-stable and readily purified, it facilitates rapid access to substituted biaryl and heterocyclic scaffolds in medicinal chemistry and materials synthesis.

Synthesis

  • Route1

    References

    • Infinity Discovery, Inc. Patent: US2008/114167 A1, 2008 ; Location in patent: Page/Page column 192 ; US 20080114167 A1
  • Route2

    References

    • US2008/114167 A1, ; Page/Page column 192 ; US 20080114167 A1

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

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Computational Chemistry Data

  • TPSA   70.78
  • LogP   1.3546
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   2

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