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

  • CAS No. 1212021-11-8

  • Cat. No. CS-0146634
  • Purity≥98%
  • MDL No.MFCD16659095

*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)benzonitrile|CS-0146634

Structure of 1212021-11-8

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General Information

  • CAS No. 1212021-11-8
  • Cat. No. CS-0146634
  • Purity ≥98%
  • MDL No. MFCD16659095
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₅BClNO₂
  • Molecular Weight 263.53
  • Synonym(s) 3-Chloro-5-cyanophenylboronic acid, pinacol ester
  • SMILES N#CC1=CC(B2OC(C)(C(C)(O2)C)C)=CC(Cl)=C1

Description

This boronate ester integrates a chloro substituent and nitrile group, enabling sequential functionalization via palladium-catalyzed cross-coupling. The tetramethyl-1,3,2-dioxaborolane moiety ensures high stability and reactivity under standard conditions.

Application

3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile serves as a versatile Suzuki-Miyaura coupling partner, enabling efficient C–C bond formation under mild conditions. The boronate ester group offers excellent stability, ease of handling, and compatibility with diverse functional groups, while the ortho-chloro and nitrile substituents provide orthogonal reactivity for sequential transformations. This compound functions as a key building block in the synthesis of biaryl scaffolds relevant to pharmaceutical and agrochemical research.

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   42.25
  • LogP   2.51088
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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