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Cas Database

98-80-6

98-80-6

Identification

  • Product Name:Phenylboronic acid

  • CAS Number: 98-80-6

  • EINECS:202-701-9

  • Molecular Weight:121.931

  • Molecular Formula: C6H7BO2

  • HS Code:29310095

  • Mol File:98-80-6.mol

Synonyms:Phenyldihydroxyborane;Borophenylic acid;Phenylboronic Acid (PBA);1/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9;Dihydroxyphenylborane;Boric acid, phenyl-;boronic acid, phenyl-;4-16-00-01654 (Beilstein Handbook Reference);Usaf bo-2;Dihydroxy(phenyl)borane;Kyselina fenylborita [Czech];Acide phenylborique [French];T-500;Acide phenylborique;Benzeneboronic acid;Phenyl boronic acid;Phenylboronic acid 98%;phenyl-Boronic acid;Boronic acid,phenyl-;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn,IrritantXi,DangerousN

  • Hazard Codes:Xn,Xi,N

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowed

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:Usbiological
  • Product Description:Phenylboronic Acid-d5
  • Packaging:100mg
  • Price:$ 355
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  • Manufacture/Brand:Usbiological
  • Product Description:Phenylboronic acid
  • Packaging:25g
  • Price:$ 322
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  • Product Description:PhenylboronicAcid(95%)
  • Packaging:10g
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Phenylboronic Acid (contains varying amounts of Anhydride)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Phenylboronic Acid (contains varying amounts of Anhydride)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Phenylboronic Acid (contains varying amounts of Anhydride)
  • Packaging:250g
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  • Manufacture/Brand:Strem Chemicals
  • Product Description:Phenylboronic acid, min. 97%
  • Packaging:50g
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  • Manufacture/Brand:Strem Chemicals
  • Product Description:Phenylboronic acid, min. 97%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Phenylboronic acid 95%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Phenylboronic acid purum, ≥97.0% (HPLC)
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Relevant articles and documentsAll total 115 Articles be found

-

Gilman,Moore

, p. 3609 (1958)

-

Catalytic phenylborylation reaction by iridium(0) nanoparticles produced from hydridoiridium carborane

Yinghuai, Zhu,Chenyan, Koh,Ang, Thiam Peng,Emi,Monalisa, Winata,Louis, Loo Kui-Jin,Hosmane, Narayan S.,Maguire, John A.

, p. 5756 - 5761 (2008)

Well-dispersed iridium(0) nanoparticles stabilized with the ionic liquid, trihexyltetradecylphosphonium methylsulfonate, [THTdP][MS], have been successfully prepared by reduction of the precursor hydridoiridium carborane, (Ph3P)2Ir(H)-(7,8-nido-C2B9H 11). The iridium nanoparticles were found to be active catalysts for arylborylation, forming boric acids. The activity of the catalyst has been investigated as a function of the activating base, and reaction conditions. The highest yield of 91% was achieved in a microwave reactor using the base, tetra-2-pyridinylpyrazine, in the presence of [THTdP][MS]. The catalytic system could be recycled at least six times with less than a 0.5% loss of activity.

Novel biscapped and monocapped tris(dioxime) Mn(II) complexes: X-ray crystal structure of the first cationic tris(dioxime) Mn(II) complex [Mn(CDOH)3BPh]OH (CDOH2 = 1,2-cyclohexanedione dioxime)

Hsieh, Wen-Yuan,Liu, Shuang

, p. 5034 - 5043 (2006)

This report describes the synthesis and characterization of a series of novel biscapped and monocapped tris-(dioxime) Mn(II) complexes [Mn(dioxime) 3(BR)2] and [Mn(dioxime)3BR]+ (dioxime = cyclohexanedione dioxime (CDOH2) and 1,2-dimethylglyoxyl dioxime (DMGH2); R = Me, n-Bu, and Ph). All tris(dioxime) Mn(II) complexes have been characterized by elemental analysis, IR, UV/vis, cyclic voltammetry, ESI-MS, and, in the cases of [Mn(CDOH)3BPh] OH·CHCl3 and [Mn(CDO)(CDOH)2(BBu(OC 2H5))2], X-ray crystallography. It was found that biscapped Mn(II) complexes [Mn(dioxime)3(BR)2] are not stable in the presence of water and readily hydrolyze to form monocapped cationic complexes [M(dioxime)3BR]+. This instability is most likely caused by mismatch between the size of Mn(II) and the coordination cavity of the biscapped tris(dioxime) ligands. In contrast, monocapped cationic complexes [M(dioxime)3BR]+ are very stable in aqueous solution even in the presence of PDTA (1,2-diaminopropane-N,N,N′,N′- tetraacetic acid) because of the kinetic inertness imposed by the monocapped tris(dioxime) chelators that are able to completely wrap Mn(II) into their N6 coordination cavity. [Mn(CDO)3BPh]OH has a distorted trigonal prismatic coordination geometry, with the Mn(II) being bonded by six imine-N donors. The hydroxyl groups from three dioxime chelating arms form very strong intramolecular hydrogen bonds with the hydroxide counterion so that the structure of [Mn(CDOH)3BPh]OH can be considered as being the clathrochelate with the hydroxide counterion as a cap .

Evaluation of borinic acids as new, fast hydrogen peroxide–responsive triggers

Gatin-Fraudet, Blaise,Ottenwelter, Roxane,Le Saux, Thomas,Norsikian, Stéphanie,Pucher, Mathilde,Lombès, Thomas,Baron, Aurélie,Durand, Philippe,Doisneau, Gilles,Bourdreux, Yann,Iorga, Bogdan I.,Erard, Marie,Jullien, Ludovic,Guianvarc’h, Dominique,Urban, Dominique,Vauzeilles, Boris

, (2021/12/23)

Hydrogen peroxide (H2O2) is responsible for numerous damages when overproduced, and its detection is crucial for a better understanding of H2O2-mediated signaling in physiological and pathological processes. For this purpose, various “off–on” small fluorescent probes relying on a boronate trigger have been prepared, and this design has also been involved in the development of H2O2-activated prodrugs or theranostic tools. However, this design suffers from slow kinetics, preventing activation by H2O2 with a short response time. Therefore, faster H2O2-reactive groups are awaited. To address this issue, we have successfully developed and characterized a prototypic borinic-based fluorescent probe containing a coumarin scaffold. We determined its in vitro kinetic constants toward H2O2-promoted oxidation. We measured 1.9 × 104 M-1·S-1 as a second-order rate constant, which is 10,000-fold faster than its well-established boronic counterpart (1.8 M-1·S-1). This improved reactivity was also effective in a cellular context, rendering borinic acids an advantageous trigger for H2O2-mediated release of effectors such as fluorescent moieties.

Fourth subgroup metal complex with rigid annular bridging structure and application of fourth subgroup metal complex

-

Paragraph 0058; 0061-0062, (2021/06/23)

The invention belongs to the technical field of olefin polymerization catalysts, and particularly relates to a fourth subgroup metal complex with a rigid annular bridging structure and an application of the fourth subgroup metal complex. The fourth subgroup metal complex provided by the invention has a structure represented by a formula (A) or a formula (B), X is halogen or alkyl; and M is titanium, zirconium or hafnium. On the basis of a non-metallocene catalyst, a bridging structure in catalyst molecules is improved and upgraded, and a brand-new metal complex with excellent catalytic performance and good high-temperature tolerance is designed; when the fourth subgroup metal complex is used as a main catalyst to catalyze olefin polymerization reaction, under the activation action of a small amount of mixed cocatalyst, the fourth subgroup metal complex can efficiently catalyze the copolymerization reaction of ethylene and alpha-olefin to obtain polyolefin with high molecular weight and high comonomer insertion rate.

Boronic Ester Based Vitrimers with Enhanced Stability via Internal Boron-Nitrogen Coordination

Zhang, Xiaoting,Wang, Shujuan,Jiang, Zikang,Li, Yu,Jing, Xinli

, p. 21852 - 21860 (2021/01/11)

Boron-containing polymers have many applications resulting from their prominent properties. Organoboron species with reversible B-O bonds have been successfully employed for the fabrication of various self-healing/healable and reprocessable polymers. However, the application of the polymers containing boronic ester or boroxine linkages is limited because of their instability to water. Herein, we report the hydrolytic stability and dynamic covalent chemistry of the nitrogen-coordinating cyclic boronic diester (NCB) linkages, and a new class of vitrimers based on NCB linkages is developed through the chemical reactions of reactive hydrogen with isocyanate. Thermodynamic and kinetic studies demonstrated that NCB linkages exhibit enhanced water and heat resistance, whereas the exchange reactions between NCB linkages can take place upon heating without any catalyst. The model compounds of NCBC-X1 and NCBC-X2 containing a urethane group and urea group, respectively, also showed higher hydrolytic stability compared to that of conventional boronic esters. Polyurethane vitrimers and poly(urea-urethane) vitrimers based on NCB linkages exhibited excellent solvent resistance and mechanical properties like general thermosets, which can be repaired, reprocessed, and recycled via the transesterification of NCB linkages upon heating. Especially, vitrimers based on NCB linkages presented improved stability to water and heat compared to those through conventional boronic esters because of the existence of N → B internal coordination. We anticipate that this work will provide a new strategy for designing the next generation of sustainable materials.

Linking Molecular Behavior to Macroscopic Properties in Ideal Dynamic Covalent Networks

Marco-Dufort, Bruno,Iten, Ramon,Tibbitt, Mark W.

supporting information, p. 15371 - 15385 (2020/10/20)

Dynamic covalent networks (DCvNs) are increasingly used in advanced materials design with applications ranging from recyclable thermosets to self-healing hydrogels. However, the relationship between the underlying chemistry at the junctions of DCvNs and their macroscopic properties is still not fully understood. In this work, we constructed a robust framework to predict how complex network behavior in DCvNs emerges from the chemical landscape of the dynamic chemistry at the junction. Ideal dynamic covalent boronic ester-based hydrogels were used as model DCvNs. We developed physical models that describe how viscoelastic properties, as measured by shear rheometry, are linked to the molecular behavior of the dynamic junction, quantified via fluorescence and NMR spectroscopy and DFT calculations. Additionally, shear rheometry was combined with Transition State Theory to quantify the kinetics and thermodynamics of network rearrangements, enabling a mechanistic understanding including preferred reaction pathways for dynamic covalent chemistries. We applied this approach to corroborate the "loose-bolt"postulate for the reaction mechanism in Wulff-type boronic acids. These findings, grounded in molecular principles, advance our understanding and rational design of dynamic polymer networks, improving our ability to predict, design, and leverage their unique properties for future applications.

Erratum: Linking molecular behavior to macroscopic properties in ideal dynamic covalent networks (Journal of the American Chemical Society (2020) 142: 36 (15371-15385) DOI: 10.1021/jacs.0c06192)

Iten, Ramon,Marco-Dufort, Bruno,Tibbitt, Mark W.

supporting information, p. 18730 - 18731 (2020/11/19)

The "concentration of functional groups, c,"was defined incorrectly on page S18 of the Supporting Information. The (Table Presented) correct definition is as follows: c is the concentration of functional groups of one of the two network components, assuming that both components are present in equal amounts. Therefore, in a network formed from tetrafunctional macromers (f = 4) and where the total molar concentration of macromers is [PEG], c = f [PEG]/2 = 4[PEG]/2 = 2[PEG]. In the original Supporting Information, we took c as the total concentration of functional groups in the network, resulting in c = 4[PEG]. This formula was incorrect and resulted in erroneous values for select Keq or Gp data reported in Table 1 (page 15374) and Figure 8 (page 15381). The corrected Table 1 and Figure 8 are shown below, and the SI has been corrected accordingly. In addition, some of these data that are quoted in the article should be changed as follows (with the corrected values highlighted in bold). On page 15374: "Keq,c = 37.5 when c = 0.02 M,""Keq was determined to be 540 ± 65. [?] corresponding to Gp = 10.9 ± 2.0 kPa,"and "Keq was quantified as 277 ± 37 from NMR and 323 from DFT, corresponding to Gp = 8.0 ± 0.8 and 9.0 kPa, respectively."On page 15381: "The rheometric data exhibited a similar increase in Keq from 75 at pH 6 to 10750 at pH 9 (Figure 8c)"and "At pH 9, Keq = 1126 ± 108 and 565 (from spectroscopy and rheology, respectively) and then decreased sharply at pH 10 to Keq = 112 and 120 (Figure 8e,f)."On page 15373 (in the Figure 2 caption): "Keq = 540 ± 65."'Table Presented' These corrections do not affect any of the conclusions of the article but only the exact value of select parameters. We apologize for these errors and for any inconvenience caused to the readers. ? Associated Content: ? Supporting Information The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.0c10406. Synthesis, sample preparation, computational and experimental methods, and model descriptions (PDF). (Figure Presented).

Process route upstream and downstream products

Process route

diphenylborinic acid
2622-89-1

diphenylborinic acid

phenylmercury(II) chloride
100-56-1

phenylmercury(II) chloride

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
Conditions Yield
With mercury dichloride;
With HgCl2;
diphenylboronchloride
3677-81-4

diphenylboronchloride

phenylmercury(II) chloride
100-56-1

phenylmercury(II) chloride

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: H2O
2: HgCl2
With H2O; HgCl2;
Conditions
Conditions Yield
With magnesium; In N,N-dimethyl-formamide; byproducts: Mg(2+); Electrolysis; electrolysis carried out in a single-compartment cell at room temp., starting materials dissolved in DMF containing KBr or n-Bu4NBr, solvent andexcess B(OCH3)3 evaporated under vacuum, medium hydrolysed at 0° C with an HCl or H2SO4 soln.; extraction with Et2O (3 x 20 ml if the solvent evaporated or 3 x 60 ml otherwise), organic phase dried over sodium or magnesium sulfate and concentrated under vacuum, side product phenol formation avoided by work-up under inert atmosphere;
45%
Conditions
Conditions Yield
bromobenzene; N,N-dimethyl-formamide; With Trimethyl borate; at 20 ℃; Electrochemical reaction; Mg consumable anode, supporting electrolyte;
With air; at 0 ℃; Further stages.; Acid hydrolysis;
45 % Turnov.
1,6-anhydro-β-D-glucopyranose 2,4-O-phenylboronate
32741-93-8

1,6-anhydro-β-D-glucopyranose 2,4-O-phenylboronate

levoglucosan
498-07-7

levoglucosan

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
Conditions Yield
With water; In dimethylsulfoxide-d6; at 20 ℃; for 1h; Inert atmosphere;
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

water
7732-18-5

water

potassium phenyltrifluoborate

potassium phenyltrifluoborate

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
Conditions Yield
With montmorillonite K10; at 25 ℃; for 1h; Time;
1,2-diphenyl-1,2-bis(dimethylamino)diboron
19127-90-3

1,2-diphenyl-1,2-bis(dimethylamino)diboron

N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
Conditions Yield
With hydrogenchloride; water; In tetrahydrofuran; byproducts: H2;
With H2O; HCl; In tetrahydrofuran; byproducts: H2;
borane
13283-31-3

borane

triphenyltin(IV) hydroxide
76-87-9

triphenyltin(IV) hydroxide

ethanolamine
141-43-5

ethanolamine

triphenylstannane
892-20-6

triphenylstannane

phenylboronic acid
98-80-6

phenylboronic acid

2-aminoethoxydiphenyl borate
15614-89-8

2-aminoethoxydiphenyl borate

Conditions
Conditions Yield
With water; In tetrahydrofuran; diethyl ether; ethanol; to THF soln. of Sn compd. added BH3 (N2, room temp.),refluxed (1 h), added H2O,stirred (30 min),extd. (Et2O), dried (MgSO4),evapd. in vac.,heated with pentane,filtered PhB(OH)2,filtrate evapd.,added Et2O,EtOH soln. of HOCH2CH2NH2 added,refluxed (30 min); filtered hot, complex pptd. by cooling, filtered; PhB(OH)2 recrystd. from H2O; compds. identified by m. p., IR, NMR;
water
7732-18-5

water

2-phenyl-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine
24341-81-9

2-phenyl-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine

naphthalene-1,8-diamine
479-27-6

naphthalene-1,8-diamine

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
Conditions Yield
In dimethylsulfoxide-d6; at 20 ℃; for 288h;
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

water
7732-18-5

water

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
Conditions Yield
In dimethylsulfoxide-d6; at 20 ℃;

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