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

  • CAS No. 947249-44-7

  • Cat. No. CS-0144933
  • Molecule weight278.11
  • Purity≥97%
  • MDL No.MFCD12923412

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

Methyl 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate|CS-0144933

Structure of 947249-44-7

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General Information

  • CAS No. 947249-44-7
  • Cat. No. CS-0144933
  • Purity ≥97%
  • MDL No. MFCD12923412
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₉BN₂O₄
  • Molecular Weight 278.11
  • Synonym(s) Methyl-2-aMino-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carboxylate
  • SMILES O=C(OC)C1=C(N)N=CC(B2OC(C)(C)C(C)(C)O2)=C1

Description

Methyl 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate delivers a boronate-functionalized pyridine scaffold with enhanced stability and solubility. This bench-stable reagent integrates seamlessly into Suzuki-Miyaura coupling workflows, enabling efficient C–C bond formation at ambient conditions. The para-aminopyridine motif provides a versatile handle for downstream derivatization.

Application

Methyl 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group enables efficient coupling under mild conditions, while the pyridine nitrogen and ester functionality offer orthogonal reactivity for downstream modifications. Bench-stable and easily purified, it facilitates rapid access to substituted nicotinamide derivatives and heterocyclic scaffolds relevant to medicinal chemistry and process development.

Safety Information

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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   83.67
  • LogP   0.7496
  • H_Acceptors   6
  • H_Donors   1
  • Rotatable_Bonds   2

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