3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Name: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide
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CAS No. 188665-74-9
Cat. No. CS-0153890
Purity≥98%
MDL No.MFCD05663886

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3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide|CS-0153890

Structure of 188665-74-9

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General Information

CAS No. 188665-74-9
Cat. No. CS-0153890
Purity ≥98%
MDL No. MFCD05663886
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₈BNO₃
Molecular Weight 247.10
Synonym(s) BenzaMide, 3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-
SMILES CC1(C(C)(OB(O1)C2=CC=CC(C(N)=O)=C2)C)C

Description

This boronate ester integrates a stable tetramethyl-dioxaborolane moiety with a benzamide scaffold, enabling efficient Suzuki-Miyaura coupling under standard conditions. The para-substituted arylboronate features enhanced hydrolytic stability and moisture tolerance, simplifying handling in synthetic workflows.

Application

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide serves as a versatile boronate building block in Suzuki-Miyaura cross-coupling reactions. Its stability under ambient conditions and tolerance to diverse functional groups enable reliable C–C bond formation with aryl halides and pseudohalides. The dioxaborolane moiety facilitates efficient coupling while the amide functionality provides orthogonal reactivity for downstream derivatization, making it a practical scaffold for medicinal chemistry and materials synthesis.

Synthesis

Route1
- In-stock
  
  618-48-4
- In-stock
  
  73183-34-3
- ~89%
- In-stock
  
  188665-74-9
References
- Billingsley, Kelvin L.; Barder, Timothy E.; Buchwald, Stephen L. Angewandte Chemie - International Edition, 2007 , vol. 46, # 28 p. 5359 - 5363

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
Precautionary Statements : P264-P270-P330-P501

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Computational Chemistry Data

TPSA 61.55
LogP 1.0847
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Amide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

CAS No. 188665-74-9

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