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4-(5,5-Dimethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde is a chemical compound that belongs to the class of benzaldehydes. It is characterized by a benzene ring substituted with a formyl group and a boron-containing heterocycle. 4-(5,5-Dimethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde is widely used in organic synthesis and as a reagent in chemical reactions, particularly for its role in cross-coupling reactions to form carbon-carbon bonds. It also serves as a building block in the synthesis of various organic compounds and materials, making it a versatile component in the fields of organic chemistry and material science.

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  • 128376-65-8 Structure
  • Basic information

    1. Product Name: 4-(5,5-Dimethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde
    2. Synonyms: AKOS BRN-0004;4-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZALDEHYDE;4-(5,5-Dimethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde;4-FORMYLPHENYLBORONIC ACID, NEOPENTYL GLYCOL CYCLIC ESTER;4-FORMYLBENZENEBORONIC ACID 2,2-DIMETHYLPROPANEDIOL-1,3 CYCLIC ESTER;2-(4-FORMYLPHENYL)-5,5-DIMETHYL-1,3,2-DIOXABORANE;4-(5,5-Dimethyl-1,3,2-dioxaborin-2-yl)benzaldehyde;4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzaldehyde, 5,5-Dimethyl-2-(4-formylphenyl)-1,3,2-dioxaborinane
    3. CAS NO:128376-65-8
    4. Molecular Formula: C12H15BO3
    5. Molecular Weight: 218.06
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 128376-65-8.mol
  • Chemical Properties

    1. Melting Point: 58-60 °C
    2. Boiling Point: 350.459 °C at 760 mmHg
    3. Flash Point: 165.752 °C
    4. Appearance: Light yellow powder
    5. Density: 1.082 g/cm3
    6. Vapor Pressure: 4.39E-05mmHg at 25°C
    7. Refractive Index: 1.504
    8. Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
    9. Solubility: N/A
    10. CAS DataBase Reference: 4-(5,5-Dimethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde(CAS DataBase Reference)
    11. NIST Chemistry Reference: 4-(5,5-Dimethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde(128376-65-8)
    12. EPA Substance Registry System: 4-(5,5-Dimethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde(128376-65-8)
  • Safety Data

    1. Hazard Codes: Xi
    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: 128376-65-8(Hazardous Substances Data)

128376-65-8 Usage

Uses

Used in Organic Synthesis:
4-(5,5-Dimethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde is used as a key intermediate in organic synthesis for the preparation of a variety of organic compounds. Its unique structure allows for the formation of carbon-carbon bonds through cross-coupling reactions, facilitating the creation of complex molecular architectures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-(5,5-Dimethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde is utilized as a building block for the synthesis of various pharmaceuticals. Its ability to participate in cross-coupling reactions makes it a valuable component in the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
4-(5,5-Dimethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde is also employed in the agrochemical industry for the synthesis of agrochemicals. Its role in forming carbon-carbon bonds is crucial for the development of new compounds with pesticidal or herbicidal properties, contributing to more effective crop protection strategies.
Used in Material Science:
In the field of material science, 4-(5,5-Dimethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde is used as a component in the synthesis of advanced materials. Its versatility in forming carbon-carbon bonds allows for the development of materials with unique properties, such as improved stability, conductivity, or other desirable characteristics for various applications.

Check Digit Verification of cas no

The CAS Registry Mumber 128376-65-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,8,3,7 and 6 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 128376-65:
(8*1)+(7*2)+(6*8)+(5*3)+(4*7)+(3*6)+(2*6)+(1*5)=148
148 % 10 = 8
So 128376-65-8 is a valid CAS Registry Number.
InChI:InChI=1/C12H15BO3/c1-12(2)8-15-13(16-9-12)11-5-3-10(7-14)4-6-11/h3-7H,8-9H2,1-2H3

128376-65-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzaldehyde

1.2 Other means of identification

Product number -
Other names 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzaldehyde

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:128376-65-8 SDS

128376-65-8Relevant articles and documents

Borylated porphyrins: 5,10,15,20-tetrakis(5,5-dimethyl-1,3,2-dioxa-borinan- 2-yl)porphyrin nitrobenzene disolvate

Muniappan, Sankar,Lipstman, Sophia,Goldberg, Israel

, p. o177-o179 (2008)

The title compound, C64H66B4N4O8·2C6H5NO2, is a nitro-benzene solvate of a meso-tetra-phenyl-porphyrin species with unconventional peripheral boronic ester substituents. The porphyrin units reside in the crystal on centers of inversion and exhibit a chann

Simultaneous Formation of a Fully Organic Triply Dynamic Combinatorial Library

Drozdz, Wojciech,Stefankiewicz, Artur R.,Walczak, Anna

, p. 3641 - 3645 (2021)

Here we report the simultaneous formation of doubly and triply dynamic libraries as a result of exchange reactions between functionalized organic building blocks. A combination of three different reversible covalent linkages involving a boronate ester transesterification along with an imine and disulfide exchange was employed to generate a new type of fully organic triply dynamic molecular assembly.

C-H activation by amide chelation control: Ruthenium-catalyzed direct synthesis of 2-Aryl-3-furanamides

Zhao, Yigang,Snieckus, Victor

supporting information, p. 1527 - 1532 (2014/06/09)

A new, catalytic methodology for the synthesis of heterobiaryls by the ruthenium-catalyzed C-H activation/cross-coupling of heterocyclic amides with aryl boroneopentylates is surveyed. From this survey, the highly regioselective reaction of furan-3-carboxamide to give 2-aryl-3-furanamides is optimized and generalized in scope with respect to the aryl boroneopentylate coupling partners. Established thereby is a one-step synthetic method which may supercede the broadly applied two-step directed ortho metalation (DoM)-cross coupling reaction involving cryogenic and strong base conditions and which has potential for further ortho and remote metalation chemistry.

Copper-catalyzed amination of arylboronates with N,N-dialkylhydroxylamines

Matsuda, Naoki,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro

supporting information; body text, p. 3642 - 3645 (2012/05/20)

A tolerant coupling: The title reaction has been developed to deliver arylamines (see scheme; Bz=benzoyl, dppbz=1,2-bis(diphenylphosphino)benzene). The catalysis is based on electrophilic, umpolung amination and enables the use of secondary acyclic amines. Various functional groups are tolerated, thus opening up a new substrate class for the Chan-Lam-type coupling.

Borylation of organo halides and triflates using tetrakis(dimethylamino) diboron

Bello, Charles S.,Schmidt-Leithoff, Joachim

, p. 6230 - 6235,6 (2012/12/11)

We report a new in situ borylation method using tetrakis(dimethylamino) diboron, DMA4B2, in the presence of a diol. Our method uses standard borylation conditions and readily available Pd-catalysts. The scope of this method includes aryl halides and triflates as well as vinyl halides and triflates. The method successfully works with a broad range of diols, enabling the selection of the best boronic ester for subsequent Suzuki coupling.

Synthesis of boradiazaindacene-imidazopyrazinone conjugate as lipophilic and yellow-chemiluminescent chemosensor for superoxide radical anion

Saito, Ryota,Ohno, Ayako,Ito, Eri

scheme or table, p. 583 - 590 (2010/09/05)

As a chemiluminescent chemosensor that emits yellow light on reacting with a superoxide radical anion (O2{radical dot}-) and has a lipophilic character, a 6-phenylimidazo[1,2-a]pyrazin-3(7H)-one derivative possessing a boradiazaindac

PROCESSES FOR THE PREPARATION OF BIPHENYL COMPOUNDS

-

Page/Page column 20; 30; 32; 33, (2010/01/29)

The invention concerns processes for the synthesis of a compound of the formula: wherein: R1 and R2 are each, independently, C1-C12 alkyl, CO2R3, OR4, R5(OR6), or C6-C18 aiyl; R3 -R6 are each, independently, C1-C12 alkyl or C6-C12 aryl; and n and m are each, independently, O or an integer from 1-5; said process comprising: — contacting a compound of the formula H0-R7-0H with BH3 and a compound of the formula in the presence of a nickel-containing catalyst to produce a first product, where R7 is a C2-C12 hydrocarbon group and X is a halogen, OMs or OTs; — contacting the first product in situ with a compound of the formula: in the presence of a nickel-containing catalyst to produce a compound of formula I, where Z is a halogen.

Carboxylation of organoboronic esters catalyzed by N-heterocyclic carbene copper(I) complexes

Ohishi, Takeshi,Nishiura, Masayoshi,Hou, Zhaomin

supporting information; experimental part, p. 5792 - 5795 (2009/03/11)

Copper complexes with a CO2 fixation: Copper(I) complexes serve as excellent catalysts for the carboxylation of aryl- and alkenylboronic esters with CO2, affording a variety of functionalized carboxylic acid derivatives (see scheme). Important active intermediates such as the copper(I) aryl and carboxylate complexes, [(IPr)CuR] and [(IPr)CuOCOR] (R = 4-MeOC 6H4, IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2- ylidene), are isolated and structurally characterized. (Chemical Equation Presented).

Two-step, one-pot ni-catalyzed neopentylglycolborylation and complementary pd/ni-catalyzed cross-coupling with aryl halides, mesylates, and tosylates

Wilson, Daniela A.,Wilson, Christopher J.,Rosen, Brad M.,Percec, Virgil

supporting information; experimental part, p. 4879 - 4882 (2009/05/31)

(Equation Presented) Two-step, one-pot neopentylglycolborylation of aryl iodides and bromides catalyzed by NiCl2(dppe) and NiCl 2(dppp) is reported. Electron-rich and electron-deficient aryl neopentylglycolboronates were efficiently cross-coupled with aryl iodides, bromides, chlorides, mesylates, and tosylates by exploiting complementary Pd/Ni and Ni/Ni catalysis. The borylation route was further extended to a three-step, one-pot synthesis of biaryls via in situ Ni-catalyzed borylation and Pd-mediated cross-coupling.

A versatile method for the hydrolysis of gem-dibromomethylarenes bearing carboxylate or boronate group into aldehydes

Augustine, John Kallikat,Naik, Y. Arthoba,Mandal, Ashis Baran,Chowdappa, Nagaraja,Praveen, Vinuthan B.

, p. 688 - 695 (2008/04/12)

Hydrolysis of gem-dibromomethylarenes bearing carboxylate or boronate group to corresponding aldehydes without affecting the ester group was successfully accomplished in high yields by subjecting them to refluxing pyridine. Both aromatic and heteroaromatic substrates gave the corresponding aldehydes in good yields. This method was efficiently adapted for the large scale synthesis of 2d and 2f.

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