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2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane, also known as Dibutylphenylvinyborane or DBPB, is a boron-containing chemical compound used in organic synthesis as a cross-coupling reagent. It has a molecular structure consisting of a boron atom bonded to four methyl groups and a phenyl group with tert-butyl substituents. DBPB is valued for its ability to facilitate the synthesis of complex organic molecules and pharmaceuticals, making it a versatile tool for chemical synthesis research and development.

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  • 2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

    Cas No: 1071924-13-4

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  • 1071924-13-4 Structure
  • Basic information

    1. Product Name: 2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane
    2. Synonyms: 2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane
    3. CAS NO:1071924-13-4
    4. Molecular Formula: C20H33BO2
    5. Molecular Weight: 316.28582
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 1071924-13-4.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: 2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
    10. NIST Chemistry Reference: 2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane(1071924-13-4)
    11. EPA Substance Registry System: 2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane(1071924-13-4)
  • 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: 1071924-13-4(Hazardous Substances Data)

1071924-13-4 Usage

Uses

Used in Pharmaceutical Industry:
2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane is used as a cross-coupling reagent for the formation of carbon-carbon and carbon-heteroatom bonds in the synthesis of complex organic molecules and pharmaceuticals. Its high stability and reactivity make it a valuable tool in the development of new drugs and therapeutic agents.
Used in Organic Synthesis Research:
2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane is used as a reagent in various coupling reactions, including Suzuki-Miyaura and Stille coupling, to facilitate the formation of carbon-carbon and carbon-heteroatom bonds. This allows for the efficient synthesis of complex organic molecules, making DBPB a versatile tool for chemical synthesis research and development.

Check Digit Verification of cas no

The CAS Registry Mumber 1071924-13-4 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,0,7,1,9,2 and 4 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 1071924-13:
(9*1)+(8*0)+(7*7)+(6*1)+(5*9)+(4*2)+(3*4)+(2*1)+(1*3)=134
134 % 10 = 4
So 1071924-13-4 is a valid CAS Registry Number.

1071924-13-4SDS

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 2-[3,5-bis(1,1-dimethylethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

1.2 Other means of identification

Product number -
Other names 2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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:1071924-13-4 SDS

1071924-13-4Relevant articles and documents

Synthesis of dilactone bridged terphenyls with crankshaft architectures

Dressler, Justin J.,Miller, Sarah A.,Meeuwsen, Brian T.,Riel, Asia Marie S.,Dahl, Bart J.

, p. 283 - 292 (2015)

Three highly fluorescent dilactone bridged terphenyls with crankshaft architectures have been synthesized. This general class of compounds is relatively unexplored. These compounds have been characterized by fluorescence and UV-vis spectroscopy. For all three compounds, a direct correlation between the rigidity of the terphenyl system and the strength of absorption and emission of light has been observed. Preliminary studies have indicated that compounds with this architecture have the potential to be useful as pH-driven molecular switches and/or sensors with instant fluorescence attenuation at high pH values.

Material for organic device and organic electroluminescent device using same (by machine translation)

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Paragraph 0624-0628, (2020/09/03)

The compound according to claim 1, which is represented by the following general formula. When a polycyclic aromatic compound having a bulky substituent in a molecule is used as a material for an organic device, an organic EL device having good quantum efficiency can be provided, for example. In particular, since the use concentration can be relatively high, concentration quenching can be suppressed, which is advantageous in the device manufacturing process. (In General Formula (1), R represents a hydrogen atom or a methyl group. 1 R/R3 R/R4 ~ R7 R/R8 ~ R11 R/R12 ~ R15 Is independently hydrogen, aryl, or the X, and X is each independently hydrogen, aryl, or the like. 1 Silver - O or — AOMARKENCODEGXDEGXDEGXDEGXDEGXDEGXDEGXDEGXDEGXDEGXDEGXDEGXDEGXDEGXDEGXDEGXDEGXDEGXDEGXDEGXDEGXDEGXDEGXDEGXDEGXDEGX1 Z2 At least 1 hydrogen in the compound of general formula (1) may be substituted with halogen or deuterium. (by machine translation)

Two Ligands Transfer from Ag to Pd: En Route to (SIPr)Pd(CF2H)(X) and Its Application in One-Pot C-H Borylation/Difluoromethylation

Herbert, Simon,Kinzel, Tom,Shen, Qilong,Zhang, Wei,Zhao, Haiwei

, p. 3596 - 3604 (2020/03/23)

A process for the concurrent transfer of both the NHC ligand and the difluoromethyl group from [(SIPr)Ag(CF2H)] to PdX2 (X = Cl, OAc, and OPiv) for the preparation of [(SIPr)Pd(CF2H)X] complexes is described. These complexes were air-stable and easily underwent transmetalation with aryl pinacol boronate/reductive elimination to generate ArCF2H in high yields. Based on this discovery, the first one-pot C-H borylation and difluoromethylation process for the preparation of difluoromethylated (hetero)arenes was developed.

Cleavage of C(aryl)?CH3 Bonds in the Absence of Directing Groups under Transition Metal Free Conditions

Dai, Peng-Fei,Ning, Xiao-Shan,Wang, Hua,Cui, Xian-Chao,Liu, Jie,Qu, Jian-Ping,Kang, Yan-Biao

supporting information, p. 5392 - 5395 (2019/03/29)

Organic chemists now can construct carbon–carbon σ-bonds selectively and sequentially, whereas methods for the selective cleavage of carbon–carbon σ-bonds, especially for unreactive hydrocarbons, remain limited. Activation by ring strain, directing groups, or in the presence of a carbonyl or a cyano group is usually required. In this work, by using a sequential strategy site-selective cleavage and borylation of C(aryl)?CH3 bonds has been developed under directing group free and transition metal free conditions. Methyl groups of various arenes are selectively cleaved and replaced by boryl groups. Mechanistic analysis suggests that it proceeds by a sequential intermolecular oxidation and coupling of a transient aryl radical, generated by radical decarboxylation, involving a pyridine-stabilized persistent boryl radical.

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND A ELECTRONIC DEVICE THEREOF

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Paragraph 0084; 0087; 0127-0129, (2018/10/24)

The present invention relates to a compound for an organic electronic element including a benzo fluorine compound and a derivative thereof, an organic electronic element utilizing the same, and an electronic device thereof. According to the present invention, the light emitting efficiency, the color purity, and the lifetime of the organic electronic element can be improved. [Reference numerals] (401) Substrate;(402) Anode;(404) Hole transport layer;(405) Light emitting layer;(406) Electron transport layer;(408) Cathode

BIPHENOL COMPOUND, OLEFIN POLYMERIZATION CATALYST USING THE SAME, AND OLEFIN POLYMER PRODUCTION METHOD

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Paragraph 0156-0158, (2017/01/26)

PROBLEM TO BE SOLVED: To provide a transition metal complex having a quadridentate ligand allowing inexpensive production through a simple synthetic route, which forms a polymerization catalyst with high catalytic activity enabling polymerization of a high-molecular mass olefin. SOLUTION: The biphenol compound is represented by general formula (1). (Q1 and Q2 are C1-20 divalent hydrocarbon groups or the like; Q3 to Q8 are H, C1-20 hydrocarbon groups or the like; T1 and T2 are C6-20 aryloxy groups, amino groups or the like; and m and n are from 0 to 2.) COPYRIGHT: (C)2015,JPOandINPIT

Iridium-Catalyzed Borylation of Primary Benzylic C-H Bonds without a Directing Group: Scope, Mechanism, and Origins of Selectivity

Larsen, Matthew A.,Wilson, Conner V.,Hartwig, John F.

supporting information, p. 8633 - 8643 (2015/07/15)

Primary benzylic boronate esters are useful intermediates in organic synthesis, but these reagents cannot be prepared by hydroboration. The benzylic C-H borylation of methylarenes would be a method to form these products, but such reactions without neat methylarene or a directing group are unknown. We report an approach to divert the borylation of methylarenes from aromatic positions to benzylic positions with a silylborane as reagent and a new iridium catalyst containing an electron-deficient phenanthroline as ligand. This system forms benzylic boronate esters selectively over the corresponding aryl boronate esters. An Ir diboryl monosilyl complex ligated by the phenanthroline was isolated and determined to be the resting state of the catalyst. Mechanistic studies show that this complex is kinetically competent to be an intermediate in the catalytic process. Kinetic studies of benzylic and aryl C-H borylation catalyzed by various Ir complexes show that the rate of aryl C-H borylation decreases with decreasing electron density at the metal center of the Ir catalyst, but that the rate of benzylic C-H borylation is less sensitive to the degree of electron density at the metal center of the Ir catalyst. Kinetic and computational studies suggest that the two borylation reactions respond differently to the degree of electron density at the metal center because they occur with different turnover-limiting steps. The turnover-limiting step in the borylation of aryl C-H bonds is known to be C-H oxidative addition, but the turnover-limiting step of the borylation of benzylic C-H bonds appears to be an isomerization prior to C-B reductive elimination.

SUBSTITUTED PYRAZOLE ANALOGUES AS RAR ANTAGONISTS

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Page/Page column 28, (2013/05/22)

The present invention provides compounds of Formula I or a pharmaceutical salt thereof; methods of treating osteoarthritis and the pain associated with osteoarthritis using the compounds; and processes for preparing the compounds.

Synthesis and characterization of monoisomeric 1,8,15,22-substituted (A3B and A2B2) phthalocyanines and phthalocyanine-fullerene dyads

Ranta, Jenni,Kumpulainen, Tatu,Lemmetyinen, Helge,Efimov, Alexander

experimental part, p. 5178 - 5194 (2010/10/03)

(Figure presented) Synthesis and characterization of three phthalocyanine-fullerene (Pc-C60) dyads, corresponding monoisomeric phthalocyanines (Pc), and building blocks, phthalonitriles, are described. Six novel bisaryl phthalonitriles were prepared by the Suzuki-Miyaura coupling reaction from trifluoromethanesulfonic acid 2,3-dicyanophenyl ester and various oxaborolanes. Two phthalonitriles were selected for the synthesis of A 3B- and A2B2-type phthalocyanines. Phthalonitrile 4 has a bulky 3,5-di-tert-butylphenyl substituent at the α-phthalo position, which forces only one regioisomer to form and greatly increases the solubility of phthalocyanine. Phthalonitrile 8 has a 3-phenylpropanol side chain at the α-position making further modifications of the side group possible. Synthesized monoisomeric A3B- and A 2B2-type phthalocyanines are modified by attachment of malonic residues. Finally, fullerene is covalently linked to phthalocyanine with one or two malonic bridges to produce Pc-C60 dyads. Due to the monoisomeric structure and increased solubility of phthalocyanines, the quality of NMR spectra of the compounds is enhanced significantly, making detailed NMR analysis of the structures possible. The synthesized dyads have different orientations of phthalocyanine and fullerene, which strongly influence the electron transfer (ET) from phthalocyanine to fullerene moiety. Fluorescence quenchings of the dyads were measured in both polar and nonpolar solvents, and in all cases, the quenching was more efficient in the polar environment. As expected, most efficient fluorescence quenching was observed for dyad 20b, with two linkers and phthalocyanine and fullerene in face-to-face orientation.

Iterative synthesis of 1,3,5-polyphenylene dendrons via C-H activation

Finke, Aaron D.,Moore, Jeffrey S.

supporting information; experimental part, p. 4851 - 4854 (2009/05/31)

(Equation Presented) An iterative synthesis of 1,3,5-polyphenylene dendrons via C-H activation/Suzuki-Miyaura coupling up to a third generation dendron is described. C-H bonds at the focal points of the dendrons are selectively borylated via iridium-catalyzed borylation, eliminating the need for reactive protecting groups. Sequential additions of low catalyst loadings efficiently borylate higher-generation dendrons, whereas higher initial catalyst loadings are less efficient.

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