(E)-Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate

Name: (E)-Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 1009307-13-4
Cat. No. CS-W008802
Purity≥95%
MDL No.MFCD09027313

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(E)-Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate|CS-W008802

Structure of 1009307-13-4

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General Information

CAS No. 1009307-13-4
Cat. No. CS-W008802
Purity ≥95%
MDL No. MFCD09027313
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₉BO₄
Molecular Weight 226.08
Synonym(s) Ethyl (2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate; Ethyl (E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-propenoate; 2-ETHOXYCARBONYLVINYLBORONIC ACID PINACOL ESTER
SMILES O=C(OCC)/C=C/B1OC(C)(C)C(C)(C)O1

Description

(E)-Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate is a bench-stable boronate ester featuring a conjugated acrylate handle. This molecule integrates seamlessly into Suzuki-Miyaura cross-coupling reactions, delivering arylated products with high efficiency under standard conditions. The tetramethyl-substituted dioxaborolane moiety enhances stability and minimizes protodeboronation, while the (E)-configured double bond ensures predictable stereochemical outcomes in downstream transformations.

Application

(E)-Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The (E)-configured vinyl boronate enables efficient formation of conjugated styrene derivatives with high stereoselectivity. Its stability under ambient conditions and compatibility with diverse functional groups facilitate straightforward purification and integration into complex molecular architectures.

Synthesis

Route1
- In-stock
  
  73183-34-3
- 623-47-2
- ~99%
- In-stock
  
  1009307-13-4
References
- Wong, Jason C.; Tang, Guozhi; Wu, Xihan; Liang, Chungen; Zhang, Zhenshan; Guo, Lei; Peng, Zhenghong; Zhang, Weixing; Lin, Xianfeng; Wang, Zhanguo; Mei, Jianghua; Chen, Junli; Pan, Song; Zhang, Nan; Liu, Yongfu; Zhou, Mingwei; Feng, Lichun; Zhao, Weili; Li, Shijie; Zhang, Chao; Zhang, Meifang; Rong, Yiping; Jin, Tai-Guang; Zhang, Xiongwen; Ren, Shuang; Ji, Ying; Zhao, Rong; She, Jin; Ren, Yi; He, Yun; Chen, Li; Xu, Chunping; Chen, Dawei; Cai, Jie; Chen, Taiping; Shan, Song; Pan, Desi; Ning, Zhiqiang; Lu, Xianping Journal of Medicinal Chemistry, 2012 , vol. 55, # 20 p. 8903 - 8925,23

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 44.76
LogP 1.7371
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Functional Group Ester

Key Words

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(E)-Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate

CAS No. 1009307-13-4

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