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2-Benzyloxyphenylboronic acid is an organic compound with the chemical formula C13H13BO3. It is a white solid and is commonly used as a reagent in various chemical reactions and processes.

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  • 190661-29-1 Structure
  • Basic information

    1. Product Name: 2-Benzyloxyphenylboronic acid
    2. Synonyms: AKOS BRN-0079;2-Benzyloxyphenylboronic Acid (contains varying amounts of Anhydride);2-BENZYLOXYBENZENEBORONIC ACID;2-BENZYLOXYPHENYLBORONIC ACID;RARECHEM AH PB 0042;O-BENZYLOXYPHENYLBORONIC ACID;2-Phenylmethoxy Phenylboronic Acid;2-BENZYLOXYPHENYLBORORNIC ACID
    3. CAS NO:190661-29-1
    4. Molecular Formula: C13H13BO3
    5. Molecular Weight: 228.05
    6. EINECS: N/A
    7. Product Categories: blocks;BoronicAcids;Boronic acids;Boronic acid;Organoborons;Aryl;Boronic Acids;Boronic Acids and Derivatives;Aryl Boronic Acids;Boronic Acids and Derivatives;Chemical Synthesis;Monosubstituted Aryl Boronic Acids;Organometallic Reagents;Boronate Ester;Potassium Trifluoroborate
    8. Mol File: 190661-29-1.mol
  • Chemical Properties

    1. Melting Point: 105-110 °C(lit.)
    2. Boiling Point: 428.7 °C at 760 mmHg
    3. Flash Point: 213 °C
    4. Appearance: /
    5. Density: 1.2 g/cm3
    6. Vapor Pressure: 4.13E-08mmHg at 25°C
    7. Refractive Index: 1.593
    8. Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
    9. Solubility: Dichloromethane, Ethyl Acetate, Methanol
    10. PKA: 8.57±0.53(Predicted)
    11. BRN: 7813704
    12. CAS DataBase Reference: 2-Benzyloxyphenylboronic acid(CAS DataBase Reference)
    13. NIST Chemistry Reference: 2-Benzyloxyphenylboronic acid(190661-29-1)
    14. EPA Substance Registry System: 2-Benzyloxyphenylboronic acid(190661-29-1)
  • Safety Data

    1. Hazard Codes: C,Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36/37/39-36
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: IRRITANT, CORROSIVE
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 190661-29-1(Hazardous Substances Data)

190661-29-1 Usage

Uses

1. Kinase Inhibitors:
2-Benzyloxyphenylboronic acid is used as a reagent for the preparation of different kinase inhibitors. Kinase inhibitors are important in the pharmaceutical industry as they play a crucial role in regulating cellular processes and are potential targets for the development of drugs to treat various diseases, including cancer.
2. Palladium Complex-Catalyzed Selective Hydroxylation:
In the field of organic chemistry, 2-Benzyloxyphenylboronic acid is used as a reactant in palladium complex-catalyzed selective hydroxylation reactions. This application is significant for the synthesis of various complex organic molecules and pharmaceutical compounds.
3. Palladium(II)-Catalyzed Oxidative Heck Reactions:
The compound is also utilized in palladium(II)-catalyzed oxidative Heck reactions, which are essential for the formation of carbon-carbon and carbon-heteroatom bonds in organic synthesis.
4. Metal-Free Electrophilic Fluorination:
2-Benzyloxyphenylboronic acid serves as a reactant in metal-free electrophilic fluorination processes. This application is valuable for the introduction of fluorine atoms into organic molecules, which can significantly alter their chemical and biological properties.
5. Suzuki-Miyaura Cross-Coupling Reactions:
The compound is used as a reactant in Suzuki-Miyaura cross-coupling reactions, a widely employed method for the formation of carbon-carbon bonds in organic synthesis. This reaction is particularly useful in the synthesis of complex molecules and biologically active compounds.
6. Suzuki Reaction:
2-Benzyloxyphenylboronic acid is also used in the Suzuki reaction, a type of cross-coupling reaction that involves the formation of carbon-carbon bonds. This reaction is widely used in the synthesis of various organic compounds, including pharmaceuticals and natural products.

Check Digit Verification of cas no

The CAS Registry Mumber 190661-29-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,0,6,6 and 1 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 190661-29:
(8*1)+(7*9)+(6*0)+(5*6)+(4*6)+(3*1)+(2*2)+(1*9)=141
141 % 10 = 1
So 190661-29-1 is a valid CAS Registry Number.
InChI:InChI=1/C13H13BO3/c15-14(16)12-8-4-5-9-13(12)17-10-11-6-2-1-3-7-11/h1-9,15-16H,10H2

190661-29-1 Well-known Company Product Price

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  • TCI America

  • (B4590)  2-Benzyloxyphenylboronic Acid (contains varying amounts of Anhydride)  

  • 190661-29-1

  • 1g

  • 590.00CNY

  • Detail
  • TCI America

  • (B4590)  2-Benzyloxyphenylboronic Acid (contains varying amounts of Anhydride)  

  • 190661-29-1

  • 5g

  • 1,990.00CNY

  • Detail
  • Alfa Aesar

  • (L20100)  2-Benzyloxybenzeneboronic acid, 96%   

  • 190661-29-1

  • 1g

  • 554.0CNY

  • Detail
  • Alfa Aesar

  • (L20100)  2-Benzyloxybenzeneboronic acid, 96%   

  • 190661-29-1

  • 5g

  • 1836.0CNY

  • Detail

190661-29-1SDS

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 (2-phenylmethoxyphenyl)boronic acid

1.2 Other means of identification

Product number -
Other names 2-(Phenylmethoxy)benzeneboronic acid 2-(Phenylmethyl)oxyphenylboronic 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:190661-29-1 SDS

190661-29-1Relevant articles and documents

Structure-Based Optimization of 3-Phenyl-N-(2-(3-phenylureido)ethyl)thiophene-2-sulfonamide Derivatives as Selective Mcl-1 Inhibitors

Li, Yan,Fan, Wenjie,Gong, Qineng,Tian, Jie,Zhou, Mi,Li, Qing,Uwituze, Laura B.,Zhang, Zhichao,Hong, Ran,Wang, Renxiao

, p. 10260 - 10285 (2021/07/26)

Selective Mcl-1 inhibitors may overcome the drug resistance caused by current anti-apoptotic Bcl-2 protein inhibitors in tumors with Mcl-1 overexpression. Based on previously discovered compounds with a 3-phenylthiophene-2-sulfonamide core moiety, in this work, we have obtained new compounds with improved binding affinity and/or selectivity under the guidance of structure-based design. The most potent compounds achieved sub-micromolar binding affinities to Mcl-1 (Ki~ 0.4 μM) and good cytotoxicity (IC5015N-heteronuclear single-quantum coherence NMR spectra suggested that these compounds bound to the BH3-binding groove on Mcl-1. Several cellular assays revealed that FWJ-D4 as well as its precursor FWJ-D5 effectively induced caspase-dependent apoptosis, and their target engagement at Mcl-1 was confirmed by co-immunoprecipitation experiments. Treatment with FWJ-D5 at 50 mg/kg every 2 days on an RS4;11 xenograft mouse model for 22 days led to 75% reduction in tumor volume without body weight loss.

Method for preparing azoxystrobin on basis of Suzuki reaction

-

, (2016/10/10)

The invention relates to a method for preparing azoxystrobin on basis of a Suzuki reaction. The method comprises the following steps: dissolving a mixture composed of methyl (E)-2-[2-(6-chloropyrimidinyl-4-yloxo)phenyl]-3-methoxy acrylate, cesium carbonate and 2-cyanophenol according to a molar ratio of 1:2:2 in a solvent, stirring at 85DEG C under the protection of N2 for 7h, and separating and purifying the obtained mixture to prepare azoxystrobin. The novel green synthesis method provided by the invention has the advantages of low cost, high yield, simple process, and suitableness for mass production.

A concise synthesis of azoxystrobin using a Suzuki cross-coupling reaction

Liu, Yong-Gan,Luo, Yan,Lu, Yao

, p. 586 - 589 (2015/11/27)

A simple, efficient and eco-friendly process for the synthesis in good yield of azoxystrobin from 2-bromophenol has been developed using phenolic hydroxyl protection, Grignard reaction, Suzuki cross-coupling, hydrogenation and a nucleophilic reaction on a 2-chloropyrimidine.

Discovery of GSK345931A: An EP1 receptor antagonist with efficacy in preclinical models of inflammatory pain

Hall, Adrian,Brown, Susan H.,Budd, Christopher,Clayton, Nicholas M.,Giblin, Gerard M.P.,Goldsmith, Paul,Hayhow, Thomas G.,Hurst, David N.,Naylor, Alan,Anthony Rawlings,Scoccitti, Tiziana,Wilson, Alexander W.,Winchester, Wendy J.

, p. 497 - 501 (2011/03/18)

Herein we describe the medicinal chemistry programme to identify a potential back-up compound to the EP1 receptor antagonist GW848687X. This work started with the lipophilic 1,2-biaryl benzene derivative 4 which displayed molecular weight of 41

Novel acyl hydrazino thiophene derivatives, process for preparing them, their use as medicinal products, pharmaceutical compositions and novel use

-

Page/Page column 17, (2010/02/12)

The invention concerns novel compounds of formula (I), process for making, pharmaceutical compositions and methods of treating diseases associated with abnormal physiological behavior in the secretion and/or the activity of cysteine proteases especially c

Stereoselective synthesis of (±)-rocaglaol analogues

Thede, Kai,Diedrichs, Nicole,Ragot, Jacques P.

, p. 4595 - 4597 (2007/10/03)

(Chemical equation presented) An intramolecular hydroxy epoxide opening was used to access the cyclopenta[d]benzofuran ring system of the natural product rocaglaol (2). Our route allowed the stereocontrolled preparation of the rocaglaol derivative (±)-(1S*,3S*,3aR*,8bS*)-3b. The synthesis of the (±)-(3R*)-epimer of 3b was also achieved. Our strategy is well-suited for the production of analogues with variation of the western ring.

Protease inhibitors

-

, (2008/06/13)

The present invention provides compounds of formula (I) which inhibit proteases, including cathepsin K, pharmaceutical compositions of such compounds, and methods for treating diseases of excessive bone loss or cartilage or matrix degradation, including osteoporosis; gingival disease including gingivitis and periodontitis; arthritis, more specifically, osteoarthritis and rheumatoid arthritis; Paget's disease; hypercalcemia or malignancy; and metabolic bone disease therewith.

Treatment of parasitic diseases by inhibition of cysteine proteases of the papain superfamily

-

, (2008/06/13)

The present invention relates to compounds and pharmaceutical compositions which inhibit proteases, such as cysteine proteases. In particular, the present invention relates to compounds and pharmaceutical compositions which inhibit cysteine proteases of the papain superfamily. The compounds and pharmaceutical compositions of the present invention are useful for treating diseases, particularly parasitic diseases, which are mediated by such proteases. In particular, the present invention relates to a method of treating malaria by inhibiting the cysteine protease falcipain.

PROTEASE INHIBITORS

-

, (2008/06/13)

Disclosed herein is a compound of the formula STR1 known as 2-[N-(N-benzyloxycarbonyl-L-leucinyl)]-2'-[N'-[4-(N,N-dimethylaminomethyl) benzyloxy]carbonyl-L-leucinyl]carbohydrazide; and pharmaceutically acceptable salts, hydrates and solvates thereof.

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