Cyclohex-1-en-1-ylboronic acid

Name: Cyclohex-1-en-1-ylboronic acid
Brand: ChemScene
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CAS No. 89490-05-1
Cat. No. CS-W007409
Purity≥97%
MDL No.MFCD02179497

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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Cyclohex-1-en-1-ylboronic acid|CS-W007409

Structure of 89490-05-1

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General Information

CAS No. 89490-05-1
Cat. No. CS-W007409
Purity ≥97%
MDL No. MFCD02179497
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₁₁BO₂
Molecular Weight 125.96
Synonym(s) Cyclohexen-1-yl-Boronic Acid
SMILES OB(C1=CCCCC1)O

Description

Cyclohex-1-en-1-ylboronic acid features a conjugated vinyl boronic acid moiety that enables efficient Suzuki-Miyaura cross-coupling reactions. This bench-stable reagent integrates readily into synthetic sequences requiring aryl or alkenyl building blocks, offering predictable regiochemistry and compatibility with diverse reaction conditions.

Application

Cyclohex-1-en-1-ylboronic acid serves as a versatile building block in transition-metal-catalyzed coupling reactions, enabling efficient C–C bond formation under mild conditions. Its pendant vinyl boronic ester functionality exhibits excellent bench stability and tolerates a range of functional groups, facilitating direct incorporation into complex molecular architectures. Widely employed in the synthesis of cyclic frameworks and bioactive heterocycles, it functions reliably in Suzuki-Miyaura cross-coupling protocols with high reproducibility and predictable regioselectivity.

Synthesis

Route1
- 212127-64-5
- ~55%
- In-stock
  
  89490-05-1
References
- Renaud; Ouellet Journal of the American Chemical Society, 1998 , vol. 120, # 31 p. 7995 - 7996
Route2
- In-stock
  
  141091-37-4
- ~%
- In-stock
  
  89490-05-1
References
- Angewandte Chemie - International Edition, , vol. 51, # 31 p. 7799 - 7803

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 40.46
LogP 0.4988
H_Acceptors 2
H_Donors 2
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Fatty ring compounds Cyclohexane compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

Key Words

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Cyclohex-1-en-1-ylboronic acid

CAS No. 89490-05-1

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