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

Name: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde
Brand: ChemScene
Availability: InStock
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CAS No. 273731-82-1
Cat. No. CS-0174951
Purity≥97%
MDL No.MFCD16295105

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde|CS-0174951

Structure of 273731-82-1

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General Information

CAS No. 273731-82-1
Cat. No. CS-0174951
Purity ≥97%
MDL No. MFCD16295105
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₅BO₄
Molecular Weight 222.05
Synonym(s) 5-Formylfuran-2-boronic acid, pinacol ester
SMILES CC1(C(C)(OB(O1)C2=CC=C(O2)C=O)C)C

Description

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde features a boronate ester group paired with a reactive aldehyde function, enabling efficient Suzuki-Miyaura cross-coupling and subsequent derivatization. This bifunctional scaffold integrates seamlessly into complex molecular architectures under mild conditions.

Application

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The furan aldehyde functionality enables sequential transformations, including oxidation, reduction, or nucleophilic addition, while the stable boronate ester tolerates a range of reaction conditions. Bench-stable and easily purified, it facilitates efficient assembly of complex heterocyclic scaffolds in medicinal chemistry and materials synthesis.

Synthesis

Route1
- In-stock
  
  76-09-5
- In-stock
  
  27329-70-0
- ~67%
- In-stock
  
  273731-82-1
References
- ZENTIVA, K.S.; RADL, Stanislav; STEFKO, Martin; CERNY, Josef Patent: WO2014/59956 A1, 2014 ; Location in patent: Page/Page column 8 ;
Route2
- In-stock
  
  13529-27-6
- 61676-62-8
- ~%
- In-stock
  
  273731-82-1
References
- ZENTIVA, K.S.; RADL, Stanislav; STEFKO, Martin; CERNY, Josef Patent: WO2014/59956 A1, 2014 ; Location in patent: Page/Page column 7 ;

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-P280-P302+P352

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Computational Chemistry Data

TPSA 48.67
LogP 1.3913
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Aldehyde

Building Blocks Skeleton Aromatic heterocycle compounds Furan compounds

Key Words

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

CAS No. 273731-82-1

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