N,N-Dimethyl-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine

Name: N,N-Dimethyl-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine
Brand: ChemScene
Availability: InStock
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CAS No. 909391-56-6
Cat. No. CS-0153843
Purity≥95%
MDL No.MFCD08669568

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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N,N-Dimethyl-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine|CS-0153843

Structure of 909391-56-6

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General Information

CAS No. 909391-56-6
Cat. No. CS-0153843
Purity ≥95%
MDL No. MFCD08669568
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₂₄BNO₂
Molecular Weight 261.17
Synonym(s) N,N-Dimethyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methylamine
SMILES CC1(C)C(C)(C)OB(C2=CC=CC(=C2)CN(C)C)O1

Description

N,N-Dimethyl-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine features a boronate ester group flanked by sterically hindered tetramethylcyclopentadienyl moieties, enhancing stability and compatibility in cross-coupling reactions. This bench-stable arylboron reagent integrates seamlessly into Suzuki-Miyaura protocols, enabling efficient C–C bond formation under mild conditions.

Application

N,N-Dimethyl-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The diborolane moiety enables reliable C–C bond formation under mild conditions, while the N,N-dimethylamino group provides enhanced solubility and stability. This compound functions effectively in late-stage functionalization and heterocycle synthesis, offering predictable reactivity and straightforward purification, making it well-suited for iterative medicinal chemistry campaigns and process-scale applications.

Synthesis

Route1
- 124-40-3
- In-stock
  
  214360-74-4
- ~75%
- In-stock
  
  909391-56-6
References
- AKZO NOBEL N.V.; PHARMACOPEIA DRUG DISCOVERY, INC. Patent: WO2006/95014 A1, 2006 ; Location in patent: Page/Page column 43-44 ; WO 2006/095014 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 : 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 21.7
LogP 2.0474
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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N,N-Dimethyl-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine

CAS No. 909391-56-6

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