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

Name: Methyl 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
Brand: ChemScene
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CAS No. 363185-87-9
Cat. No. CS-0175552
Purity≥95%
MDL No.MFCD16293749

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Methyl 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate|CS-0175552

Structure of 363185-87-9

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General Information

CAS No. 363185-87-9
Cat. No. CS-0175552
Purity ≥95%
MDL No. MFCD16293749
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₂₀BNO₄
Molecular Weight None
Synonym(s) Methyl 2-aMino-5-(tetraMethyl-1,3,2-dioxaborolan-2-yl)benzoate
SMILES CC1(C(C)(OB(O1)C2=CC(C(OC)=O)=C(N)C=C2)C)C

Description

Methyl 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate features a boronate ester group enabling reliable Suzuki-Miyaura coupling under mild conditions. The para-amino substituent enhances electronic tuning and facilitates downstream functionalization. This bench-stable reagent integrates efficiently into complex molecule synthesis with minimal side reactions.

Application

Methyl 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate serves as a versatile boron building block for Suzuki-Miyaura cross-coupling reactions. The pinacol borane moiety ensures excellent bench stability and functional group tolerance, enabling efficient C–C bond formation under mild conditions. The ortho-amino and ester functionalities provide strategic handles for further derivatization in medicinal chemistry and heterocycle synthesis, making it a practical reagent for constructing complex aromatic scaffolds.

Synthesis

Route1
- In-stock
  
  73183-34-3
- In-stock
  
  52727-57-8
- ~%
- In-stock
  
  363185-87-9
References
- WO2007/80382 A1, ; Page/Page column 130 ; WO 2007/080382 A1
Route2
- In-stock
  
  77317-55-6
- 25015-63-8
- ~%
- In-stock
  
  363185-87-9
References
- EP1270577 A1, ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H225
Precautionary Statements : P210-P233-P240-P241-P242-P243-P280-P370+P378-P501

Quality Control

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Computational Chemistry Data

TPSA 70.78
LogP 1.3546
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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

CAS No. 363185-87-9

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