(E)-2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol

Name: (E)-2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 581802-26-8
Cat. No. CS-W018867
Purity≥95%
MDL No.MFCD10698506

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(E)-2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol|CS-W018867

Structure of 581802-26-8

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General Information

CAS No. 581802-26-8
Cat. No. CS-W018867
Purity ≥95%
MDL No. MFCD10698506
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₂₁BO₃
Molecular Weight 212.09
Synonym(s) None
SMILES CC(C)(O)\C=C\B1OC(C)(C)C(C)(C)O1

Description

This boronate ester features a (E)-configured enol moiety flanked by a methyl group and a tetramethyl-1,3,2-dioxaborolane ring. The conjugated alkene system enables efficient cross-coupling reactions under mild conditions, while the sterically protected boronate offers enhanced stability during storage and handling. This compound integrates readily into complex molecular architectures via Suzuki-Miyaura coupling protocols.

Application

(E)-2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol serves as a stable, bench-ready boronate building block for palladium-catalyzed cross-coupling reactions. Its vinyl boronate functionality enables efficient Suzuki-Miyaura coupling with aryl, heteroaryl, and vinyl halides under mild conditions. The tetramethylcyclohexadienylboronate moiety enhances stability and minimizes protodeboronation, while the tertiary alcohol group provides orthogonal reactivity in multi-step syntheses. Functions reliably in complex molecule assembly and API intermediate construction.

Synthesis

Route1
- 1138162-60-3
- ~49%
- In-stock
  
  581802-26-8
References
- Berree, Fabienne; Gernigon, Nicolas; Hercouet, Alain; Chia, Hui Lin; Carboni, Bertrand European Journal of Organic Chemistry, 2009 , # 3 p. 329 - 333
Route2
- 115-19-5
- In-stock
  
  73183-34-3
- ~92%
- In-stock
  
  581802-26-8
References
- Zhao, Jie; Niu, Zhiqiang; Fu, Hua; Li, Yadong Chemical Communications, 2014 , vol. 50, # 16 p. 2058 - 2060
Route3
- 17869-77-1
- 25015-63-8
- ~78%
- In-stock
  
  581802-26-8
References
- McLaughlin, Mark G.; Cook, Matthew J. Chemical Communications, 2011 , vol. 47, # 39 p. 11104 - 11106

Safety Information

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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 38.69
LogP 1.9449
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Fatty chain compounds

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(E)-2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol

CAS No. 581802-26-8

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