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(E)-2-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol is a complex organic chemical compound that integrates elements such as carbon, hydrogen, oxygen, and boron. It is characterized by a carbon chain with a multiple bond, classifying it within the alkene group. (E)-2-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol's structure is enriched with various functional groups, including alcohols and boronic esters, which are commonly involved in organic reactions such as the Suzuki coupling. (E)-2-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol's exact applications and properties may differ depending on the specific context in which it is used, and it requires careful handling due to its potential reactivity.

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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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  • 581802-26-8 Structure
  • Basic information

    1. Product Name: (E)-2-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol
    2. Synonyms: (E)-2-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol;(E)-(3-Hydroxy-3-methylbuten-1-yl)boronic acid pinacol ester;(3E)-2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-buten-2-ol;-2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl);(E)-2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)but-3-enyl-2-ol
    3. CAS NO:581802-26-8
    4. Molecular Formula: C11H21BO3
    5. Molecular Weight: 212.09364
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 581802-26-8.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 70-80 °C(Press: 0.1 Torr)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 0.97±0.1 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: 2-8°C
    8. Solubility: N/A
    9. PKA: 14.71±0.29(Predicted)
    10. CAS DataBase Reference: (E)-2-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol(CAS DataBase Reference)
    11. NIST Chemistry Reference: (E)-2-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol(581802-26-8)
    12. EPA Substance Registry System: (E)-2-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol(581802-26-8)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 581802-26-8(Hazardous Substances Data)

581802-26-8 Usage

Uses

Used in Organic Synthesis:
(E)-2-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol is used as a synthetic intermediate for the preparation of more complex organic molecules. Its presence of boronic ester groups makes it a valuable building block in cross-coupling reactions, such as the Suzuki reaction, which is a powerful method for the formation of carbon-carbon bonds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (E)-2-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol is used as a key component in the synthesis of potential drug candidates. Its versatility in organic reactions allows for the creation of a wide range of molecular structures that could exhibit therapeutic properties.
Used in Material Science:
(E)-2-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol is employed in the development of new materials with specific properties, such as improved thermal stability or enhanced electrical conductivity. Its structural features can be tailored to meet the requirements of various applications in material science.
Used in Research and Development:
In academic and industrial research settings, (E)-2-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-ol is utilized as a model compound to study the reactivity and behavior of complex organic molecules. This can lead to a better understanding of reaction mechanisms and the development of new synthetic strategies.

Check Digit Verification of cas no

The CAS Registry Mumber 581802-26-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 5,8,1,8,0 and 2 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 581802-26:
(8*5)+(7*8)+(6*1)+(5*8)+(4*0)+(3*2)+(2*2)+(1*6)=158
158 % 10 = 8
So 581802-26-8 is a valid CAS Registry Number.

581802-26-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

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

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:581802-26-8 SDS

581802-26-8Relevant articles and documents

Highly efficient hydroboration of alkynes catalyzed by porous copper-organic framework under mild conditions

Gao, Ning,Hu, Tianding,Kang, Xiaomin,Lan, Xingwang,Wang, Zhenguang,Wu, Zhi-Lei,Zhao, Bin

, p. 250 - 257 (2021/10/25)

The hydroboration of alkynes is crucial due to the wide applications in organic synthesis, while such reaction is often completed with low turnover frequency (TOF) value and long reaction time. Therefore, it is very important and necessary that the hydrob

Zirconium-Catalyzed Synthesis of Alkenylaminoboranes: From a Reliable Preparation of Alkenylboronates to a Direct Stereodivergent Access to Alkenyl Bromides

Birepinte, Mélodie,Chabaud, Laurent,Liautard, Virginie,Pucheault, Mathieu

, p. 2838 - 2843 (2020/04/16)

A simple procedure has been optimized for the preparation of alkenylaminoborane from alkynes using diisopropylaminoborane and HZrCp2Cl. Coupled with a magnesium-catalyzed dehydrogenation, it allowed for the use of air- and moisture-stable diisopropylamine. This synthesis has been extended to a one-pot sequence leading directly to bromoalkenes with controlled stereochemistry. As such, it provides an easy, scalable, cheap process to access alkenylboronates and both (E)- and (Z)-bromoalkenes from commercially available alkynes.

Synthesis of Alkenyl Boronates from Epoxides with Di-[B(pin)]-methane via Pd-Catalyzed Dehydroboration

Murray, Stephanie A.,Luc, Eugenia C. M.,Meek, Simon J.

supporting information, p. 469 - 472 (2018/01/28)

A practical and broadly applicable catalytic method for the synthesis of (E)-alkenylborons is presented. Reactions are promoted by [Pd(Cl)(η3-C3H5)]2 and proceed by the dehydroboration of cyclic borates. Through

Efficient heterogeneous hydroboration of alkynes: enhancing the catalytic activity by Cu(0) incorporated CuFe2O4 nanoparticles

Zeng, Xianghua,Gong, Chunhua,Guo, Haiyang,Xu, Hao,Zhang, Junyong,Xie, Jingli

supporting information, p. 17346 - 17350 (2018/11/01)

CuFe2O4 magnetic nanoparticles (NPs) are typically further calcined at high temperature to eliminate the reduced state of the Cu(0) source. Here we report the discovery of Cu(0) incorporated in CuFe2O4 that enables the catalytic activity for hydroboration of alkynes to be enhanced. This catalyst system has a low working temperature and short reacting time, and wide tolerance of substituted alkynes such as ynoate, ynamide and ynone. The Cu-CuFe2O4 catalyst was prepared by a simple hydrothermal method and well characterized by SEM, TEM, PXRD, XPS and EDS. Recycling of the catalyst was also achieved without obvious loss of activity after six runs. Furthermore, the mechanism of this reaction was also investigated.

Rhodium-Catalysed Hydroboration of Terminal Alkynes Using Pinacolborane Promoted by Tri(2-furyl)phosphine

Wang, Kongchen,Bates, Roderick W.

supporting information, p. 2749 - 2752 (2017/06/13)

Tri(2-furyl)phosphine is a superior ligand to triphenylphosphine in the rhodium-catalysed hydroboration of alkynes with pinacolborane to yield alkenylboronates. In general the reactions are faster and the products are cleaner.

Ligand-free hydroboration of alkynes catalyzed by heterogeneous copper powder with high efficiency

Zhao, Jie,Niu, Zhiqiang,Fu, Hua,Li, Yadong

supporting information, p. 2058 - 2060 (2014/03/21)

Regioselective hydroboration of terminal and internal alkynes is realized by using 10 mol% copper powder (0.3-1 μm) at room temperature. 24 alkynes were efficiently converted into vinylboronates in up to 96% yield without addition of any ligand or additiv

PtCl2/XPhos: A highly efficient and readily available catalyst for the hydrosilylation of propargylic alcohols

McLaughlin, Mark G.,Cook, Matthew J.

supporting information; experimental part, p. 11104 - 11106 (2011/11/07)

A highly regioselective hydrosilylation of propargylic alcohols has been developed using an in situ prepared PtCl2/XPhos catalyst system. The reaction is tolerant of many functional groups and exhibits excellent regio and geometric selectivity.

SN2′ boron-mediated Mitsunobu reactions - A new one-pot three-component synthesis of substituted enamides and enol benzoates

Berree, Fabienne,Gernigon, Nicolas,Hercouet, Alain,Chia, Hui Lin,Carboni, Bertrand

supporting information; experimental part, p. 329 - 333 (2009/07/04)

The conversion of (3-hydroxy-1-propen-1-yl)boronates to substituted enamides and enol benzoates is readily achieved in a one-pot procedure consisting of a regiocontrolled Mitsunobu reaction with convenient nucleophiles, followed by allylboration of aldehydes. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.

Synthesis of functionalized vinyl boronates via ruthenium-catalyzed olefin cross-metathesis and subsequent conversion to vinyl halides

Morrill, Christie,Grubbs, Robert H.

, p. 6031 - 6034 (2007/10/03)

Functionalized vinyl pinacol boronates suitable for Suzuki cross-coupling reactions are synthesized using ruthenium-catalyzed olefin cross-metathesis of 1-propenyl pinacol boronate and various alkenes, including functionalized and 1,1-disubstituted alkenes. The resultant boronate cross products are stereoselectively transformed into predominantly Z-vinyl bromides and E-vinyl iodides. The vinyl bromides may be synthesized in a two-step, one-pot synthesis from a variety of olefins, resulting in a Z-selective formal vinyl bromide cross-metathesis reaction.

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