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3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

  • CAS No. 1269233-11-5

  • Cat. No. CS-0310915
  • Purity≥98%
  • MDL No.None

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

3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-0310915

Structure of 1269233-11-5

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General Information

  • CAS No. 1269233-11-5
  • Cat. No. CS-0310915
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₇BClNO₂
  • Molecular Weight 253.53
  • Synonym(s) None
  • SMILES NC1=CC(B2OC(C)(C)C(C)(C)O2)=CC(Cl)=C1

Description

3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline features a boronate ester group flanked by tetramethylcyclopentadienone rings, enabling stable coupling under Suzuki-Miyaura conditions. The chloro substituent provides orthogonal reactivity for sequential functionalization. This arylboronate integrates readily into complex scaffolds with high chemoselectivity and minimal protodeboronation.

Application

3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The pendant chloro group enables sequential functionalization, while the sterically protected boronate moiety offers excellent shelf stability and compatibility with diverse reaction conditions. Its ortho-directed reactivity facilitates efficient construction of biaryl scaffolds and complex heterocycles in medicinal chemistry and materials science applications.

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   44.48
  • LogP   2.2214
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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