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4-(Dimethylamino)phenylboronic acid is an organic compound with the chemical formula C8H12BNO2. It is a white to green-grey or blue-grey crystalline substance known for its unique chemical properties and versatile applications in various industries.

28611-39-4

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28611-39-4 Usage

Uses

Used in Chemical Synthesis:
4-(Dimethylamino)phenylboronic acid is used as a reactant/reagent in the preparation of biaryls via palladium-catalyzed Suzuki-Miyaura coupling of nitroarenes with boronic acids. This reaction is a widely employed method in organic chemistry for the formation of carbon-carbon bonds, particularly in the synthesis of complex molecules and pharmaceuticals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-(Dimethylamino)phenylboronic acid is utilized as a key intermediate in the synthesis of various drugs and drug candidates. Its unique chemical properties allow for the development of novel therapeutic agents with potential applications in treating a range of diseases.
Used in Material Science:
4-(Dimethylamino)phenylboronic acid can also be employed in the development of new materials with specific properties, such as optical, electronic, or mechanical characteristics. Its ability to form stable complexes with other molecules makes it a valuable component in the design and synthesis of advanced materials for various applications.
Used in Research and Development:
Due to its unique chemical properties and reactivity, 4-(Dimethylamino)phenylboronic acid is often used in research and development laboratories for the exploration of new chemical reactions, synthesis methods, and potential applications in various fields, including chemistry, biology, and materials science.

Check Digit Verification of cas no

The CAS Registry Mumber 28611-39-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,8,6,1 and 1 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 28611-39:
(7*2)+(6*8)+(5*6)+(4*1)+(3*1)+(2*3)+(1*9)=114
114 % 10 = 4
So 28611-39-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H12BNO2/c1-10(2)8-5-3-7(4-6-8)9(11)12/h3-6,11-12H,1-2H3

28611-39-4 Well-known Company Product Price

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  • (Code)Product description
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  • TCI America

  • (D4428)  4-(Dimethylamino)phenylboronic Acid (contains varying amounts of Anhydride)  

  • 28611-39-4

  • 1g

  • 1,130.00CNY

  • Detail
  • TCI America

  • (D4428)  4-(Dimethylamino)phenylboronic Acid (contains varying amounts of Anhydride)  

  • 28611-39-4

  • 5g

  • 3,890.00CNY

  • Detail
  • Alfa Aesar

  • (H55723)  4-(Dimethylamino)benzeneboronic acid, 97%   

  • 28611-39-4

  • 1g

  • 558.0CNY

  • Detail
  • Alfa Aesar

  • (H55723)  4-(Dimethylamino)benzeneboronic acid, 97%   

  • 28611-39-4

  • 5g

  • 1933.0CNY

  • Detail
  • Alfa Aesar

  • (H55723)  4-(Dimethylamino)benzeneboronic acid, 97%   

  • 28611-39-4

  • 25g

  • 6762.0CNY

  • Detail

28611-39-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name [4-(dimethylamino)phenyl]boronic acid

1.2 Other means of identification

Product number -
Other names 4-(Dimethylamino)benzeneboronic Acid

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:28611-39-4 SDS

28611-39-4Relevant articles and documents

Mimicking Photosystem I with a Transmembrane Light Harvester and Energy Transfer-Induced Photoreduction in Phospholipid Bilayers

Pannwitz, Andrea,Saaring, Holden,Beztsinna, Nataliia,Li, Xinmeng,Siegler, Maxime A.,Bonnet, Sylvestre

, p. 3013 - 3018 (2021)

Photosystem I (PS I) is a transmembrane protein that assembles perpendicular to the membrane, and performs light harvesting, energy transfer, and electron transfer to a final, water-soluble electron acceptor. We present here a supramolecular model of it formed by a bicationic oligofluorene 12+ bound to the bisanionic photoredox catalyst eosin Y (EY2?) in phospholipid bilayers. According to confocal microscopy, molecular modeling, and time dependent density functional theory calculations, 12+ prefers to align perpendicularly to the lipid bilayer. In presence of EY2?, a strong complex is formed (Ka=2.1±0.1×106 m?1), which upon excitation of 12+ leads to efficient energy transfer to EY2?. Follow-up electron transfer from the excited state of EY2? to the water-soluble electron donor EDTA was shown via UV–Vis absorption spectroscopy. Overall, controlled self-assembly and photochemistry within the membrane provides an unprecedented yet simple synthetic functional mimic of PS I.

Impact of Five-membered Heterocyclic Rings on Photophysical Properties including Two-photon Absorption Character

Abe, Manabu,Chitose, Youhei,Lin, Tzu-Chau,Pham, Thuy Thi Thu,Tam, Tran Thi Thanh,Tseng, Wei-Lun

supporting information, p. 1810 - 1813 (2021/10/27)

A series of dipolar-type terphenyl derivatives 13 featuring an electron donor (p-NMe2C6H4 group) and acceptor (p-NO2C6H4 group) unit was synthesized and their photophysical properties were

Magnesium promoted autocatalytic dehydrogenation of amine borane complexes: A reliable, non-cryogenic, scalable access to boronic acids

Marciasini, Ludovic D.,Richard, Jimmy,Cacciuttolo, Bastien,Sartori, Guillaume,Birepinte, Melodie,Chabaud, Laurent,Pinet, Sandra,Pucheault, Mathieu

, p. 164 - 171 (2018/12/05)

Owing to the unusual reactivity of dialkylamine-borane complexes, a methodology was developed to simply access boronic acids. The intrinsic instability of magnesium aminoborohydride was tweaked into a tandem dehydrogenation borylation sequence. Proceeding via an autocatalytic cycle, amineborane dehydrogenation was induced by a variety of Grignard reagents. Overall, addition of the organomagnesium species onto specially designed dialkylamine-borane complexes led to a variety of boronic acids in high yields. In addition, the reaction can be performed under Barbier conditions, on a large scale.

Benzacridine derivatives and organic light-emitting device (OLED) thereof

-

Paragraph 0057; 0058; 0059, (2018/07/30)

The invention provides benzacridine derivatives and an organic light-emitting device (OLED) thereof, and relates to the technical field of organic optoelectronic materials. The compounds has the advantages of simple preparation method and easy obtaining of raw materials, have better hole transmission efficiency, film-forming property and thermal stability. Furthermore, the compounds also can be applied to a light extraction layer of the device, and can effectively reduce driving voltage and increase light-emitting efficiency, thus being light extraction materials with good performance.

Fluorescent chemosensors of carbohydrate triols exhibiting TICT emissions

Oesch, David,Luedtke, Nathan W.

, p. 12641 - 12644 (2015/08/06)

4-4′-Disubstituted biphenyl boronic acids (BBAs) are push-pull fluorophores with "turn-on" fluorescence properties. Upon carbohydrate triol binding, BBA boronate esters can participate in photon-induced electron transfer, giving a twisted intramolecular charge transfer (TICT) complex. The resulting TICT emissions distinguish between carbohydrates that bind to boron as a diol versus triol unit, thereby revealing stereochemical information about the carbohydrate.

Sequential one-pot access to molecular diversity through aniline aqueous borylation

Erb, William,Albini, Mathieu,Rouden, Jacques,Blanchet, Jrme

, p. 10568 - 10580 (2015/01/08)

On the basis of our recently reported aniline aqueous borylation, molecular diversity was achieved in a one-pot process by combining other reactions such as esterification, Suzuki-Miyaura coupling, hydrogenolysis, or Petasis borono-Mannich.

Synthesis and biological activity of new 4-(Pyridin-4-yl)-(3-methoxy-5- methylphenyl)- 1H-pyrazoles derivatives as ROS Receptor tyrosine kinase inhibitors

Park, Byung Sun,El-deeb, Ibrahim M.,Yoo, Kyung Ho,Han, Dong Keun,Tae, Jin Sung,Lee, So Ha

, p. 3629 - 3634 (2013/01/16)

A series of new 4-(pyridin-4-yl)-(3-methoxy-5-methylphenyl)-1H-pyrazoles (6a-k & 7a-l) has been rationally designed based on the structure of the lead compound KIST301080, a selective ROS receptor tyrosine kinase inhibitor, in order to study the activity of ROS of this new class of inhibitors. The compounds were synthesized and screened against ROS kinase, where compound 6h showed moderate inhibitory activity with an IC50 value of 6.25 μM. The study emphasized the importance of the acetonitrile group at the pyrazole ring and also the importance of having a hydrogen bond donor on the distal phenyl ring linked to the pyridine moiety.

Highly efficient one-pot access to functionalized arylboronic acids via noncryogenic bromine/magnesium exchanges

Leermann, Timo,Leroux, Frederic R.,Colobert, Francoise

supporting information; experimental part, p. 4479 - 4481 (2011/10/09)

A general and convenient protocol for the electrophilic borylation of aryl Grignard reagents prepared from arylbromides by direct insertion of magnesium in the presence of LiCl or by Mg/Br exchange with iPrMgCl?LiCl has been developed. Various aryl boronic acids were synthesized in a straightforward manner in excellent yields at 0 °C.

Red-emitting dyes with photophysical and photochemical properties controlled by pH

Novakova, Veronika,Miletin, Miroslav,Kopecky, Kamil,Zimcik, Petr

experimental part, p. 14273 - 14282 (2012/01/06)

New unsymmetrical zinc azaphthalocyanines, bearing one substituted aniline as a peripheral substituent, were prepared by using a statistical condensation approach. Both fluorescence and singlet oxygen quantum yields were extremely low in DMF (φFΔF=0. 22-0.29, φΔ=0.40-0.59, respectively). This behavior was attributed to the deactivation of excited states by intramolecular charge transfer from a donor site (aniline), which was blocked after protonation in acidic media. In the protonated form, all of the compounds efficiently emitted light with λem in the region of 662-675 nm. The investigated compounds were anchored to dioleoylphosphatidylcholine (DOPC) unilamellar vesicles and showed response to buffer pH. They were highly fluorescent at low pH values and almost nonfluorescent in neutral solutions. The pKa values were determined in DOPC vesicles and ranged between 2.2 and 4.2.

Molecular motion in zinc hydrazone grid complexes

Dutta, Manisha,Movassat, Meisam,Brook, David J.R.,Oliver, Allen,Ward, Don

experimental part, p. 632 - 643 (2012/03/27)

Four new grid forming hydrazone ligands substituted with methoxy and dimethylamino groups were synthesised. Combination of these ligands with zinc triflate in acetonitrile resulted in self-assembly to form grids as indicated by 1H NMR and ES-MS

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