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

  • CAS No. 1269233-01-3

  • Cat. No. CS-0109769
  • Purity≥95%
  • MDL No.None

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

2-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-0109769

Structure of 1269233-01-3

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General Information

  • CAS No. 1269233-01-3
  • Cat. No. CS-0109769
  • Purity ≥95%
  • 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) 2-chloro-5-(tetramethyl-1,3,2-dioxaborolan-2-al)aniline
  • SMILES ClC1=C(C=CC=C1N)B2OC(C)(C(C)(O2)C)C

Description

This boronate-functional aniline integrates seamlessly into Suzuki-Miyaura cross-coupling reactions, offering enhanced stability and compatibility under standard conditions. The ortho-chloro substituent enables selective derivatization, while the tetramethylcyclopentadienylboronate moiety ensures efficient coupling with aryl halides.

Application

2-Chloro-3-(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 ortho-chloro substituent enables selective functionalization, while the pinacol boronate group offers excellent stability, ease of handling, and compatibility with a broad range of reaction conditions. This reagent facilitates efficient construction of biaryl scaffolds 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-P305+P351+P338-P330-P362+P364-P403+P233-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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