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126747-14-6

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126747-14-6 Usage

Description

4-Cyanophenylboronic acid can be used for palladium catalyzed Suzuki cross-coupling reactions to synthesize 6-acryl-2,4-diamino-pyrimidines and triazines. It is used as precursor in the synthesis of inhibitors such as Tpl2 kinase inhibitors and P2X7 antagonists used in the treatment of pain.?It is also a reagent used for preparation of himbacine analogs as thrombin receptor antagonists and potential antiplatelet agents, trisulfonated calixarene upper-rim sulfonamido and their complexation with trimethyllysine epigenetic mark, antimalarial compounds via Suzuki cross-coupling, and deoxyuridine derivatives.

Reference

G. Cooke, H. A. de Cremiers, V. M. Rotello, B. Tarbit, P. E. Vanderstr?ten, Synthesis of 6-aryl-2,4-diamino-pyrimidines and triazines using palladium catalysed Suzuki cross-coupling reactions, Tetrahedron, 2001, vol. 57, pp. 2787-2789 N. Ni, H. Chou, J. Wang, M. Li, C. Lu, P. C. Tai, B. Wang, Identification of boronic acids as antagonists of bacterial quorum sensing in Vibrio harveyi, Biochemical and Biophysical Research Communications, 2008, vol. 369, pp. 590-594

Chemical Properties

white to yellow powder

Uses

Different sources of media describe the Uses of 126747-14-6 differently. You can refer to the following data:
1. suzuki reaction
2. 4-Cyanophenylboronic Acid is a reactant used in the synthesis of (AMG-8718), an inhibitor of β-site amyloid precursor protein cleaving enzyme (BACE1).
3. Intermediates of Liquid Crystals

Check Digit Verification of cas no

The CAS Registry Mumber 126747-14-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,6,7,4 and 7 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 126747-14:
(8*1)+(7*2)+(6*6)+(5*7)+(4*4)+(3*7)+(2*1)+(1*4)=136
136 % 10 = 6
So 126747-14-6 is a valid CAS Registry Number.
InChI:InChI=1/C7H6BNO2/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4,10-11H

126747-14-6 Well-known Company Product Price

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  • TCI America

  • (C1778)  4-Cyanophenylboronic Acid (contains varying amounts of Anhydride)  

  • 126747-14-6

  • 1g

  • 120.00CNY

  • Detail
  • TCI America

  • (C1778)  4-Cyanophenylboronic Acid (contains varying amounts of Anhydride)  

  • 126747-14-6

  • 5g

  • 350.00CNY

  • Detail
  • TCI America

  • (C1778)  4-Cyanophenylboronic Acid (contains varying amounts of Anhydride)  

  • 126747-14-6

  • 25g

  • 1,100.00CNY

  • Detail
  • Alfa Aesar

  • (L18007)  4-Cyanobenzeneboronic acid, 98%   

  • 126747-14-6

  • 1g

  • 482.0CNY

  • Detail
  • Alfa Aesar

  • (L18007)  4-Cyanobenzeneboronic acid, 98%   

  • 126747-14-6

  • 5g

  • 1591.0CNY

  • Detail

126747-14-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Cyanophenylboronic acid

1.2 Other means of identification

Product number -
Other names 4-Cyanophenylboronic 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:126747-14-6 SDS

126747-14-6Relevant articles and documents

Synthesis and photophysical properties of a series of thermally stable terphenyl-bridged bisbenzimidazoles

Luo, Zhonghua,Zhu, Hongjun,Song, Guangliang,Chang, Jin,Liu, Rui

, p. 274 - 279 (2011)

Nine novel terphenyl-bridged bisbenzimidazoles were synthesized in high yield by the condensation of o-phenylenediamines and terphenyl dinitriles in the presence of polyphosphoric acid. The bisbenzimidazoles are thermally robust with high decomposition te

Triarylamine-based dual-function coadsorbents with extended π-conjugation aryl linkers for organic dye-sensitized solar cells

Choi, In Taek,You, Ban Seok,Eom, Yu Kyung,Ju, Myung Jong,Choi, Won Seok,Kang, Sung Ho,Kang, Min Soo,Seo, Kang Deuk,Hong, Ji Yeoun,Song, Sang Hyun,Yang, Ji-Woon,Kim, Hwan Kyu

, p. 3316 - 3326 (2014)

Triarylamine-based dual-function coadsorbents containing a carboxylic acid acceptor linked by extended π-conjugation aryl linkers (e.g., phenylene: HC-A3, naphthalene: HC-A4 and anthracene: HC-A5) were newly designed and synthesized. They were used as coadsorbents in organic dye-sensitized solar cells (DSSCs) based on a porphyrin dye (hexyloxy-biphenyl-ZnP-CN-COOH (HOP)). For comparison, the π-conjugated phenyl linker (HC-A3) previously developed by our group was also used as a coadsorbent. The structural effects on the photophysical and electrochemical properties and DSSC performance were systematically investigated. As a result, the DSSCs based on HC-A4 and HC-5 displayed power conversion efficiencies (PCEs) of 8.2% and 5.1%, respectively, while the HC-A3-based DSSC achieved a PCE of 7.7%. In the case of HC-A4, both the short-circuit photocurrent densities (Jsc) and open-circuit voltages (Voc) of DSSCs were simultaneously improved to a large extent due to the more effective prevention of π-π stacking of organic dye molecules and the better light-harvesting effect at short wavelengths. The HC-A5-based DSSC exhibited a much lower short-circuit current (Jsc) and open-circuit voltages (Voc) compared to the HC-A4-based DSSC, due to the fact that the dihedral angle of the π-conjugated linkers was too high for electron injection into the TiO2 conduction band (CB) level. This had a reduced effect on preventing the π-π stacking of dye molecules, resulting in lower Jsc and Voc values.

Synthesis and thermal analysis of disubstituted propiolates bearing terphenylene mesogen

Chen, Lie,Chen, Yiwang,Zhou, Weihua,He, Xiaohui,Song, Yanlin,Zhang, Zhijie

, p. 391 - 397 (2010)

Novel disubstituted propiolates bearing chromophoric terphenylene mesogenic groups, namely, 40-cyano- 4-terphenylyl-2-octynate M(CN) and 40-methoxyl-4-terphenylyl- 2-octynate M(OCH3) are synthesized, where the terphenyl groups are connected to the C≡C through ester linkage directly. Using transition-metal catalysts such as the classical MoCl 5- and WCl6-based metathesis catalysts, the polymerization of the M(CN) and M(OCH3) are carried out in a series of different solution, however, did not obtain any products. It suggests that the WCl 6- and MoCl5-based catalysts are poisoned by the polar groups, on the other hand, the bulk terphenyl groups and the long alkyl chain around the C≡C bond might inhibit the reaction. M(CN) displays monotropic nematicity, whereas M(OCH3) exhibits enantiotropic nematicity and smecticity (SmAd) with a bilayer arrangement when cooled and heated. Ultraviolet spectroscopy and photoluminescence measurements also show that the terphenyl groups endow disubstituted propiolates with strong UV light absorption and high photoluminescence. Akademiai Kiado, Budapest, Hungary 2009.

Nimesulide derivatives and preparation method and application thereof

-

Page/Page column 13-15; 17-19; 21-22, (2019/04/26)

The invention relates to a preparation method of four nimesulide derivatives with the function of treating liver malignant tumors. According to the invention, a nimesulide solution and an acid or alkaline substance are subjected to displacement reaction to generate three salts with better water solubility and more stability, which are the nimesulide derivatives, or p-aminobenzonitrile is used as asubstrate, the fourth nimesulide derivative with higher bioavailability is generated through a series of redox reactions, four novel nimesulide derivatives are successfully prepared, all the four compounds are soluble in water, the solubility is better than that of the nimesulide, and better absorption rate and bioavailability are provided, and the hepatotoxicity of the four derivatives is not obviously different from that of the nimesulide at normal dose, and only one derivative is enhanced in liver toxicity at overdose. The inhibitory effect on BEL-7402 is no less than or even stronger thanthat of nimesulide when the four derivatives are co-cultured with CIK cells. The four nimesulide derivatives can be used for preparing drugs for inhibiting human liver cancer cells.

Development of a Concise Multikilogram Synthesis of LPA-1 Antagonist BMS-986020 via a Tandem Borylation-Suzuki Procedure

Smith, Michael J.,Lawler, Michael J.,Kopp, Nathaniel,McLeod, Douglas D.,Davulcu, Akin H.,Lin, Dong,Katipally, Kishta,Sfouggatakis, Chris

, p. 1859 - 1863 (2017/11/24)

The process development for the synthesis of BMS-986020 (1) via a palladium catalyzed tandem borylation/Suzuki reaction is described. Evaluation of conditions culminated in an efficient borylation procedure using tetrahydroxydiboron followed by a tandem Suzuki reaction employing the same commercially available palladium catalyst for both steps. This methodology addressed shortcomings of early synthetic routes and was ultimately used for the multikilogram scale synthesis of the active pharmaceutical ingredient 1. Further evaluation of the borylation reaction showed useful reactivity with a range of substituted aryl bromides and iodides as coupling partners. These findings represent a practical, efficient, mild, and scalable method for borylation.

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