2-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Name: 2-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 287944-10-9
Cat. No. CS-W004785
Purity≥97%
MDL No.MFCD08669391

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2-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W004785

Structure of 287944-10-9

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General Information

CAS No. 287944-10-9
Cat. No. CS-W004785
Purity ≥97%
MDL No. MFCD08669391
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₉BO₂
Molecular Weight 194.08
Synonym(s) 1-Cyclopentenylboronic acid pinacol ester
SMILES CC1(C)C(C)(C)OB(C2=CCCC2)O1

Description

This boronate ester features a cyclopentenyl group tethered to a stable dioxaborolane ring, enabling efficient cross-coupling reactions under standard conditions. The sterically hindered tetramethyl substitution enhances shelf life and resistance to protodeboronation, while the electron-deficient cyclopentenyl moiety facilitates selective functionalization in complex synthesis workflows.

Application

2-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. Its cyclopentenyl moiety enables efficient incorporation into functionalized heterocycles and conjugated systems, with excellent tolerance to common reaction conditions. The tetramethyl-substituted dioxaborolane enhances shelf stability and facilitates straightforward purification, making it well-suited for iterative synthesis in medicinal chemistry and materials development workflows.

Synthesis

Route1
- 930-29-0
- In-stock
  
  73183-34-3
- ~97%
- In-stock
  
  287944-10-9
References
- BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WAGNER, Holger; BERTA, Daniela; FUCHS, Klaus; GIOVANNINI, Riccardo; HAMPRECHT, Wolfgang; KONETZKI, Ingo; STREICHER, Ruediger; TRIESELMANN, Thomas Patent: WO2012/110599 A1, 2012 ; Location in patent: Page/Page column 230-231 ; WO 2012/110599 A1
Route2
- 61676-62-8
- In-stock
  
  17529-98-5
- ~80%
- In-stock
  
  287944-10-9
References
- Rauniyar, Vivek; Zhai, Huimin; Hall, Dennis G. Synthetic Communications, 2008 , vol. 38, # 22 p. 3984 - 3995
Route3
- 28075-49-2
- In-stock
  
  73183-34-3
- ~71%
- In-stock
  
  287944-10-9
References
- Takagi, Jun; Takahashi, Kou; Ishiyama, Tatsuo; Miyaura, Norio Journal of the American Chemical Society, 2002 , vol. 124, # 27 p. 8001 - 8006

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

Quality Control

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Computational Chemistry Data

TPSA 18.46
LogP 2.7281
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Fatty ring compounds Cyclopentane compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

Key Words

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2-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

CAS No. 287944-10-9

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