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4-Butylphenylboronic acid pinacol ester is a chemical compound that is commonly used in organic synthesis as a boronic acid derivative. It is an ester of pinacol, a type of alcohol, and 4-butylphenylboronic acid, which is a boronic acid substituted with a butyl group. Its unique structure and reactivity make it a valuable intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds.

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  • 625458-85-7 Structure
  • Basic information

    1. Product Name: 4-Butylphenylboronic acid pinacol ester
    2. Synonyms: 4-Butylphenylboronic acid pinacol ester;2-(4-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
    3. CAS NO:625458-85-7
    4. Molecular Formula: C16H25BO2
    5. Molecular Weight: 260.1795
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 625458-85-7.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 345.2±21.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 0.96±0.1 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: 4-Butylphenylboronic acid pinacol ester(CAS DataBase Reference)
    10. NIST Chemistry Reference: 4-Butylphenylboronic acid pinacol ester(625458-85-7)
    11. EPA Substance Registry System: 4-Butylphenylboronic acid pinacol ester(625458-85-7)
  • 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: 625458-85-7(Hazardous Substances Data)

625458-85-7 Usage

Uses

Used in Pharmaceutical Industry:
4-Butylphenylboronic acid pinacol ester is used as a reagent in Suzuki-Miyaura cross-coupling reactions for the formation of carbon-carbon bonds to create new organic molecules. This is crucial in the development of new pharmaceuticals with improved efficacy and safety profiles.
Used in Agrochemical Industry:
4-Butylphenylboronic acid pinacol ester is used as a reagent in Suzuki-Miyaura cross-coupling reactions to synthesize agrochemicals with enhanced properties, such as increased effectiveness and reduced environmental impact.
Used in Organic Synthesis:
4-Butylphenylboronic acid pinacol ester is used as a versatile intermediate in the synthesis of various organic compounds, including those with potential applications in materials science, fragrances, and dyes. Its reactivity in cross-coupling reactions allows for the creation of complex molecular structures with diverse functional groups.

Check Digit Verification of cas no

The CAS Registry Mumber 625458-85-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 6,2,5,4,5 and 8 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 625458-85:
(8*6)+(7*2)+(6*5)+(5*4)+(4*5)+(3*8)+(2*8)+(1*5)=177
177 % 10 = 7
So 625458-85-7 is a valid CAS Registry Number.

625458-85-7SDS

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

1.2 Other means of identification

Product number -
Other names AMTB390

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:625458-85-7 SDS

625458-85-7Relevant articles and documents

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.

Azo bond formation on metal surfaces

Meng, Xiangzhi,Klaasen, Henning,Viergutz, Lena,Schulze Lammers, Bertram,Witteler, Melanie C.,M?nig, Harry,Amirjalayer, Saeed,Liu, Lacheng,Neugebauer, Johannes,Gao, Hong-Ying,Studer, Armido,Fuchs, Harald

supporting information, p. 1458 - 1464 (2020/12/14)

The formation of azo compounds via redox cross-coupling of nitroarenes and arylamines, challenging in solution phase chemistry, is achieved by on-surface chemistry. Reaction products are analyzed with a cryogenic scanning tunneling microscope (STM) and X-ray photoelectron spectroscopy (XPS). By using well-designed precursors containing both an amino and a nitro functionality, azo polymers are prepared on surface via highly efficient nitro-amino cross-coupling. Experiments conducted on other substrates and surface orientations reveal that the metal surface has a significant effect on the reaction efficiency. The reaction was further found to proceed from partially oxidized/reduced precursors in dimerization reactions, shedding light on the mechanism that was studied by DFT calculations.

Visible-Light-Induced Ni-Catalyzed Radical Borylation of Chloroarenes

Tian, Ya-Ming,Guo, Xiao-Ning,Krummenacher, Ivo,Wu, Zhu,Nitsch, J?rn,Braunschweig, Holger,Radius, Udo,Marder, Todd B.

supporting information, p. 18231 - 18242 (2020/11/02)

A highly selective and general photoinduced C-Cl borylation protocol that employs [Ni(IMes)2] (IMes = 1,3-dimesitylimidazoline-2-ylidene) for the radical borylation of chloroarenes is reported. This photoinduced system operates with visible light (400 nm) and achieves borylation of a wide range of chloroarenes with B2pin2 at room temperature in excellent yields and with high selectivity, thereby demonstrating its broad utility and functional group tolerance. Mechanistic investigations suggest that the borylation reactions proceed via a radical process. EPR studies demonstrate that [Ni(IMes)2] undergoes very fast chlorine atom abstraction from aryl chlorides to give [NiI(IMes)2Cl] and aryl radicals. Control experiments indicate that light promotes the reaction of [NiI(IMes)2Cl] with aryl chlorides generating additional aryl radicals and [NiII(IMes)2Cl2]. The aryl radicals react with an anionic sp2-sp3 diborane [B2pin2(OMe)]- formed from B2pin2 and KOMe to yield the corresponding borylation product and the [Bpin(OMe)]?- radical anion, which reduces [NiII(IMes)2Cl2] under irradiation to regenerate [NiI(IMes)2Cl] and [Ni(IMes)2] for the next catalytic cycle.

Nickel-Catalyzed C(sp2)-H Borylation of Arenes

Das, Arpan,Hota, Pradip Kumar,Mandal, Swadhin K.

, p. 3286 - 3293 (2019/09/12)

In this study, C(sp2)-H borylation of arenes was accomplished by a nickel catalyst, resulting in good yield. Alkyl and alkoxy arenes were successfully functionalized, affording C(sp2)-H borylated compounds. It was unraveled that the well-defined abnormal N-heterocyclic carbene based Ni(II) complex breaks into Ni nanoparticles (Ni-NPs), which act as catalytically active species. A series of controlled reactions under stoichiometric conditions along with spectroscopic studies and single-crystal X-ray crystallographic study helped us to understand the formation of Ni-NPs along with formation of a boron(III) compound during this reaction.

Nickel-catalysed decarbonylative borylation of aroyl fluorides

Wang, Zhenhua,Wang, Xiu,Nishihara, Yasushi

, p. 13969 - 13972 (2019/01/03)

The first Ni(cod)2/PPh3 catalyst system has been established for decarbonylative borylation of aroyl fluorides with bis(pinacolato)diboron. A wide range of functional groups in the substrates were well tolerated. The ease of access of the starting aroyl fluorides indicates that these results might become an alternative to the existing decarbonylation events.

Highly Soluble p-Terphenyl and Fluorene Derivatives as Efficient Dopants in Plastic Scintillators for Sensitive Nuclear Material Detection

Yemam, Henok A.,Mahl, Adam,Tinkham, Jonathan S.,Koubek, Joshua T.,Greife, Uwe,Sellinger, Alan

supporting information, p. 8921 - 8931 (2017/07/11)

Plastic scintillators are commonly used as first-line detectors for special nuclear materials. Current state-of-the-art plastic scintillators based on poly(vinyltoluene) (PVT) matrices containing high loadings (>15.0 wt %) of 2,5-diphenyloxazole (PPO) off

2-Aryl-indenylphosphine ligands: Design, synthesis and application in Pd-catalyzed Suzuki-Miyaura coupling reactions

Lian, Ze-Yu,Yuan, Jia,Yan, Meng-Qi,Liu, Yan,Luo, Xue,Wu, Qing-Guo,Liu, Sheng-Hua,Chen, Jian,Zhu, Xiao-Lei,Yu, Guang-Ao

supporting information, p. 10090 - 10094 (2016/11/06)

A focused library of phosphine ligands was constructed for structural optimization. The catalyst can be used to perform the Suzuki-Miyaura cross-coupling reaction of aryl and heteroaryl chlorides.

MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS

-

Page/Page column, (2014/05/25)

Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidase (SpsB), an essential protein in bacteria.

The synthesis of 2 6-dialkylphenyldithieno[3 2-b:2' 3'-d]thiophene derivatives and their applications in organic field-effect transistors

Zhu, Minliang,Luo, Hao,Wang, Liping,Guo, Yunlong,Zhang, Weifeng,Liu, Yunqi,Yu, Gui

, p. 17 - 24 (2013/06/27)

2,6-Dialkylphenyldithieno[3,2-b:2',3'-d]thiophene derivatives (DPCn-DTT) were synthesized and characterized. Effect of alkyl groups on optical characteristics, electrochemical properties, film-forming ability, and field-effect performance was studied. The

LIQUID CRYSTAL COMPOUND

-

Page/Page column 6-7, (2012/10/23)

A liquid crystal compound with high optical anisotropy is provided. The liquid crystal compound is represented by formula (I), wherein each of R1 and R2 represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms;

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