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4,4,5,5-Tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane is a boron-based chemical compound that serves as a versatile building block in organic synthesis. Characterized by a boron atom bonded to two oxygen atoms and a carbon atom, this dioxaborolane structure is known for its stability and high reactivity. The presence of the 4-vinylphenyl group in the molecule offers flexibility for further derivatization, making it a valuable tool for the synthesis of pharmaceuticals, agrochemicals, and materials for advanced technologies.

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  • 870004-04-9 Structure
  • Basic information

    1. Product Name: 4,4,5,5-Tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane
    2. Synonyms: 4,4,5,5-Tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane
    3. CAS NO:870004-04-9
    4. Molecular Formula: C14H19BO2
    5. Molecular Weight: 230.12
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 870004-04-9.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 323.5±21.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 0.98±0.1 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
    8. Solubility: N/A
    9. CAS DataBase Reference: 4,4,5,5-Tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane(CAS DataBase Reference)
    10. NIST Chemistry Reference: 4,4,5,5-Tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane(870004-04-9)
    11. EPA Substance Registry System: 4,4,5,5-Tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane(870004-04-9)
  • 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: 870004-04-9(Hazardous Substances Data)

870004-04-9 Usage

Uses

Used in Organic Synthesis:
4,4,5,5-Tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane is used as a reagent in cross-coupling reactions for the formation of carbon-carbon bonds. Its high reactivity and stability make it a valuable component in the synthesis of various functional materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4,4,5,5-Tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane is used as a key intermediate in the synthesis of various drugs. Its versatility allows for the development of new pharmaceutical compounds with improved properties and therapeutic effects.
Used in Agrochemical Industry:
4,4,5,5-Tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane is utilized as a building block in the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural chemicals with enhanced efficacy and selectivity.
Used in Advanced Materials:
This chemical compound is also used in the preparation of materials for advanced technologies, such as polymers, coatings, and electronic materials, due to its unique structural properties and reactivity.

Check Digit Verification of cas no

The CAS Registry Mumber 870004-04-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,7,0,0,0 and 4 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 870004-04:
(8*8)+(7*7)+(6*0)+(5*0)+(4*0)+(3*4)+(2*0)+(1*4)=129
129 % 10 = 9
So 870004-04-9 is a valid CAS Registry Number.

870004-04-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 4,4,5,5-tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane

1.2 Other means of identification

Product number -
Other names 4-vinylaniline

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:870004-04-9 SDS

870004-04-9Relevant articles and documents

Tunable Hydrogen Release from Amine–Boranes via their Insertion into Functional Polystyrenes

Ledoux, Audrey,Brunet, Juliette,Raynaud, Jean,Lac?te, Emmanuel

, p. 15239 - 15243 (2019)

Polystyrene-g-boramine random copolymers are dihydrogen reservoirs with tunable dehydrogenation temperatures, which can be adjusted by selecting the boramine content in the copolymers. They display a unique dihydrogen thermal release profile, which is a d

Facile strategy to well-defined water-soluble boronic acid (Co)polymers

Cambre, Jennifer N.,Roy, Debashish,Gondi, Sudershan R.,Sumerlin, Brent S.

, p. 10348 - 10349 (2007)

A facile route to well-defined boronic acid (co)polymers from stable and easily manipulated boronic ester monomers is presented. The polymerization of 4-pinacolatoborylstyrene by reversible addition-fragmentation chain transfer (RAFT) yielded polymeric bo

One-step preparation of phenyl boron-modified magnetic mesoporous silica for selective enrichment of cis-diol-containing substances

Fu, Hua,Hu, Jing,Zhang, Min,Wang, Yuerong,Zhang, Hongyang,Hu, Ping

, (2018)

For enrichment and separation of cis-diol-containing compounds from biomatrix, a new type of magnetic nanoparticles named MS-48-PBSC, whichwas facilely prepared in a one-step heterogeneous reaction. The morphology results demonstrated that the MS-48-PBSC

High Glass-Transition Temperature Polymer Networks Harnessing the Dynamic Ring Opening of Pinacol Boronates

Brunet, Juliette,Collas, Franck,Humbert, Matthieu,Perrin, Lionel,Brunel, Fabrice,Lac?te, Emmanuel,Montarnal, Damien,Raynaud, Jean

, p. 12216 - 12222 (2019)

Differential scanning calorimetry of high molar mass poly(4-vinylphenylboronic acid, pinacol ester)s evidenced unusual reactive events above 120 °C, resulting in a high glass-transition temperature of 220 °C. A reversible ring-opening reactivity of pinaco

Functionalized styrene synthesis via palladium-catalyzed C[sbnd]C cleavage of aryl ketones

Zhang, Xu,Wang, Zhen-Yu,Wang, Xing,Xu, Hui,Dai, Hui-Xiong

, (2022/03/31)

We report herein the synthesis of functionalized styrenes via palladium-catalyzed Suzuki–Miyaura cross-coupling reaction between aryl ketone derivatives and potassium vinyltrifluoroborate. The employment of pyridine-oxazoline ligand was the key to the cleavage of unstrained C[sbnd]C bond. A variety of functional groups and biologically important moleculars were well tolerated. The orthogonal Suzuki–Miyaura coupling demonstrated the synthetic practicability.

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Vinyl Acetate in Dimethyl Isosorbide as a Sustainable Solvent

Su, Mincong,Huang, Xia,Lei, Chuanhu,Jin, Jian

supporting information, p. 354 - 358 (2022/01/15)

A nickel-catalyzed reductive cross-coupling has been achieved using (hetero)aryl bromides and vinyl acetate as the coupling partners. This mild, applicable method provides a reliable access to a variety of vinyl arenes, heteroarenes, and benzoheterocycles, which should expand the chemical space of precursors to fine chemicals and polymers. Importantly, a sustainable solvent, dimethyl isosorbide, is used, making this protocol more attractive from the point of view of green chemistry.

Merging Iridium-Catalyzed C-H Borylations with Palladium-Catalyzed Cross-Couplings Using Triorganoindium Reagents

Jayasundara, Chathurika R. K.,Gil-Negrete, José M.,Montero Bastidas, Jose R.,Chhabra, Arzoo,Martínez, M. Montserrat,Pérez Sestelo, José,Smith, Milton R.,Maleczka, Robert E.

, p. 751 - 759 (2021/12/27)

A versatile and efficient method to prepare borylated arenes furnished with alkyl, alkenyl, alkynyl, aryl, and heteroaryl functional groups is developed by merging Ir-catalyzed C-H borylations (CHB) with a chemoselective palladium-catalyzed cross-coupling of triorganoindium reagents (Sarandeses-Sestelo coupling) with aryl halides bearing a boronic ester substituent. Using triorganoindium cross-coupling reactions to introduce unsaturated moieties enables the synthesis of borylated arenes that would be difficult to access through the direct application of the CHB methodology. The sequential double catalyzed procedure can be also performed in one vessel.

Transition metal-free formal hydro/deuteromethylthiolation of unactivated alkenes

Chen, Shuangyang,Wang, Jia,Xie, Lan-Gui

supporting information, p. 4037 - 4042 (2021/05/19)

Methylthioether is involved in the methylthiotransfer process in organisms, and therefore its functionality is of paramount importance to living organisms. Several methods for the installation of the methylthio group in small molecules have been reported previously; however, procedures starting from unactivated alkenes are rare. Herein, we report a formal hydro/deuteromethylthiolation of alkenes by using dimethyl(methylthio)sulfonium trifluoromethanesulfonate as the stimulator and sodium borohydride/deuteride as the hydrogen/deuterium source. The process represents a mild, transition metal-free and methanethiol-free route towards the synthesis of methylthioethers from unactivated alkenes. This journal is

Iminyl-Radical-Promoted C-C Bond Cleavage/Heck-Like Coupling via Dual Cobaloxime and Photoredox Catalysis

Tu, Jia-Lin,Tang, Wan,Xu, Wei,Liu, Feng

, p. 2929 - 2940 (2021/02/06)

We report herein an unprecedented protocol for radical-olefin coupling of α-imino-oxy acids and alkenes for the synthesis of alkene-containing nitriles via synergistic photoredox and cobaloxime catalysis. With visible-light irradiation, the transformation

Photoinduced Hydrocarboxylation via Thiol-Catalyzed Delivery of Formate across Activated Alkenes

Alektiar, Sara N.,Wickens, Zachary K.

supporting information, p. 13022 - 13028 (2021/09/03)

Herein we disclose a new photochemical process to prepare carboxylic acids from formate salts and alkenes. This redox-neutral hydrocarboxylation proceeds in high yields across diverse functionalized alkene substrates with excellent regioselectivity. This operationally simple procedure can be readily scaled in batch at low photocatalyst loading (0.01% photocatalyst). Furthermore, this new reaction can leverage commercially available formate carbon isotologues to enable the direct synthesis of isotopically labeled carboxylic acids. Mechanistic studies support the working model involving a thiol-catalyzed radical chain process wherein the atoms from formate are delivered across the alkene substrate via CO2?- as a key reactive intermediate.

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