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CAS

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3-Formylphenylboronic acid is an organic compound that features a boronic acid group attached to a formyl-substituted phenyl ring. It is known for its unique chemical properties and reactivity, making it a versatile molecule in various chemical and biological applications.

87199-16-4

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87199-16-4 Usage

Uses

Used in Chemical Research:
3-Formylphenylboronic acid is used as a reagent to study the effects of boronic acid on fluoride-selective chemosignaling behavior of merocyanine dye. This application is crucial for understanding the interactions between boronic acids and other chemical species, which can be instrumental in developing new sensors and materials.
Used in Biophysical Studies:
As exciton-coupled CD probes for epigallocatechin gallate, 3-Formylphenylboronic acid aids in the investigation of molecular interactions and conformational changes in biological systems. This use is valuable for advancing our knowledge of biomolecular structures and their functions.
Used in Enzyme Inhibition:
3-Formylphenylboronic acid serves as a biological inhibitor of γ-glutamyltranspeptidase, an enzyme involved in the metabolism of glutathione. Its inhibitory action can be harnessed in the development of therapeutic agents targeting specific metabolic pathways.
Used in Organic Synthesis:
In the field of organic synthesis, 3-Formylphenylboronic acid is utilized as a reactant in palladium-catalyzed homocoupling reactions. This process allows for the formation of biaryl compounds, which are important structural motifs in pharmaceuticals and agrochemicals.
Used in Cross-Coupling Reactions:
3-Formylphenylboronic acid is a key component in Suzuki coupling reactions, a widely used cross-coupling method for the formation of carbon-carbon bonds. This reaction is essential for the synthesis of complex organic molecules and the development of new chemical entities.

Check Digit Verification of cas no

The CAS Registry Mumber 87199-16-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,7,1,9 and 9 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 87199-16:
(7*8)+(6*7)+(5*1)+(4*9)+(3*9)+(2*1)+(1*6)=174
174 % 10 = 4
So 87199-16-4 is a valid CAS Registry Number.
InChI:InChI=1/C7H7BO3/c9-5-6-2-1-3-7(4-6)8(10)11/h1-5,10-11H

87199-16-4 Well-known Company Product Price

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  • (Code)Product description
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  • TCI America

  • (F0445)  3-Formylphenylboronic Acid (contains varying amounts of Anhydride)  

  • 87199-16-4

  • 1g

  • 80.00CNY

  • Detail
  • TCI America

  • (F0445)  3-Formylphenylboronic Acid (contains varying amounts of Anhydride)  

  • 87199-16-4

  • 5g

  • 200.00CNY

  • Detail
  • TCI America

  • (F0445)  3-Formylphenylboronic Acid (contains varying amounts of Anhydride)  

  • 87199-16-4

  • 25g

  • 600.00CNY

  • Detail
  • Alfa Aesar

  • (B25437)  3-Formylbenzeneboronic acid   

  • 87199-16-4

  • 1g

  • 229.0CNY

  • Detail
  • Alfa Aesar

  • (B25437)  3-Formylbenzeneboronic acid   

  • 87199-16-4

  • 5g

  • 761.0CNY

  • Detail
  • Alfa Aesar

  • (B25437)  3-Formylbenzeneboronic acid   

  • 87199-16-4

  • 25g

  • 3130.0CNY

  • Detail

87199-16-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Formylphenylboronic acid

1.2 Other means of identification

Product number -
Other names (3-formylphenyl)boronic 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:87199-16-4 SDS

87199-16-4Relevant articles and documents

Copper-Catalyzed Monoorganylation of Trialkyl Borates with Functionalized Organozinc Pivalates

Fu, Ying,Gou, Bei-Lei,Shi, Chun-Zhao,Du, Zhengyin,Shen, Tong

, p. 4253 - 4257 (2018/09/18)

Organozinc pivalates, a recently developed air- and moisture-stable organozinc species, were found for the first time as excellent organometallic species in the monoorganylation of trialkyl borates whereby boronic acids were prepared in high yields. The significant advantage of organozinc pivalates over another previously employed organometallic reagents, e. g., organolithium reagents, Grignard reagents and organozinc halides, is that the generation of multiorganylation byproducts such as borinic acids and trialkylboranes were completely suppressed. Additionally, the in situ generated boronates could be directly arranged into Suzuki-Miyaura type cross-coupling reactions to produce biaryls in high yields.

Method for synthesizing aromatic aldehyde, aromatic ketone and aromatic ester through catalytically oxidizing alkyl aromatic compound by iron

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Paragraph 0092; 0093, (2017/10/13)

The invention discloses a method for synthesizing aromatic aldehyde, aromatic ketone and aromatic ester through catalytically oxidizing an alkyl aromatic compound by iron, and belongs to the technical field of catalytic synthesis. According to the method, a low-cost and environment-friendly iron catalyst is used under a normal pressure; under the action of hydrogen and silicon reagents serving as an accelerant and an oxidant, a side chain of an aromatic hydrocarbon is oxidized into a carbonyl group for generating the corresponding aromatic aldehyde, aromatic ketone and aromatic ester. The method for preparing the aromatic aldehyde, the aromatic ketone and the aromatic ester through a catalytic oxidation reaction, which is provided by the invention, has numerous advantages that a catalyst, reaction raw materials, the oxidant and a silicon reagent are wide in sources and good in stability and is low-cost and environment-friendly; the alkyl aromatic compound is metered to participate in a reaction; the reaction condition is mild; the compatibility of functional groups is good; the scope of application is wide; the reaction selectivity is good; in an optimized reaction condition, the separation yield of a target product can be up to approximately 95 percent.

A process for preparing aldehyde group benzene boric acid

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Paragraph 0026; 0027; 0033; 0036; 0037, (2017/07/04)

The invention discloses a method for preparing formyl phenylboronic acid, which comprises the following steps: heating halogenated phenylboronic acid in toluene or heptane under reflux for dewatering to form a tripolymer, mixing the tripolymer with dimethylformamide, dropwisely adding n-butyllithium at low temperature to react by a one-pot process, hydrolyzing with hydrochloric acid, and recrystallizing to obtain the formyl phenylboronic acid. The method is simple to operate, avoids the process of separating the intermediate after formyl protection in the conventional technique, has high universality, can obtain favorable yield for ortho-, meta- and para- formyl phenylboronic acids, and is beneficial to scale-up production.

Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid

Molander, Gary A.,Trice, Sarah L. J.,Kennedy, Steven M.,Dreher, Spencer D.,Tudge, Matthew T.

supporting information; experimental part, p. 11667 - 11673 (2012/09/05)

The Suzuki-Miyaura reaction has become one of the more useful tools for synthetic organic chemists. Until recently, there did not exist a direct way to make the most important component in the coupling reaction, namely the boronic acid. Current methods to make boronic acids often employ harsh or wasteful reagents to prepare boronic acid derivatives and require additional steps to afford the desired boronic acid. The scope of the previously reported palladium-catalyzed, direct boronic acid synthesis is unveiled, which includes a wide array of synthetically useful aryl electrophiles. It makes use of the newly available second generation Buchwald XPhos preformed palladium catalyst and bis-boronic acid. For ease of isolation and to preserve the often sensitive C-B bond, all boronic acids were readily converted to their more stable trifluoroborate counterparts.

Palladium-catalyzed borylation of aryl and heteroaryl halides utilizing tetrakis(dimethylamino)diboron: One step greener

Molander, Gary A.,Trice, Sarah L. J.,Kennedy, Steven M.

supporting information, p. 4814 - 4817,4 (2012/12/12)

The palladium-catalyzed borylation of aryl and heteroaryl halides with a novel borylating agent, tetrakis(dimethylamino)diboron [(Me2N) 2B-B(NMe2)2], is reported. The method is complementary to the previously reported method utilizing bis-boronic acid (BBA) in that certain substrates perform better under one set of optimized reaction conditions than the other. Because tetrakis(dimethylamino)diboron is the synthetic precursor to both BBA and bis(pinacolato)diboron (B 2Pin2), the new method represents a more atom-economical and efficient approach to current borylation methods.

Base free aryl coupling of diazonium compounds and boronic esters: Self-activation allowing an overall highly practical process

Bonin, Helene,Delbrayelle, Dominique,Demonchaux, Patrice,Gras, Emmanuel

supporting information; experimental part, p. 2677 - 2679 (2010/07/08)

Boronic esters have long been considered as poor partners in cross-coupling reactions with arene diazoniums. Here is reported an unprecedented application of self-activated boronic esters in a base-free cross-coupling reaction with diazonium salts under mild and user friendly conditions.

NOVEL BIAROMATIC COMPOUNDS WHICH ACTIVATE PPARγ TYPE RECEPTORS, AND USE THEREOF IN COSMETIC OR PHARMACEUTICAL COMPOSITIONS

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Page 58, (2008/06/13)

The invention relates to novel biaromatic compounds which correspond to the general formula (I), and also to a process for preparing them and to their use in pharmaceutical compositions intended for use in human or veterinary medicine (in dermatology, and also in the field of cardiovascular diseases, immune diseases and/or diseases associated with lipid metabolism), or alternatively in cosmetic compositions.

Method for producing formylphenylboronic acids

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, (2008/06/13)

A process for preparing formylphenylboronic acids of the formula (I) by reaction of protected chlorobenzaldehydes of the formula (II) with lithium in an inert solvent to form compounds of the formula (III) and subsequent reaction with a boron compound of the formula BY3 to give compounds of the formula (I).

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