664364-43-6

Basic information

• Product Name: 4-Cyano-1-naphthyl boronic acid
• Synonyms: 4-Cyano-1-naphthyl boronic acid;(4-cyanonaphthalen-1-yl)boronic acid
• CAS NO: 664364-43-6
• Molecular Formula: C11H8BNO2
• Molecular Weight: 196.99772
• Mol File: 664364-43-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Cyano-1-naphthyl boronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Cyano-1-naphthyl boronic acid(664364-43-6)
• EPA Substance Registry System: 4-Cyano-1-naphthyl boronic acid(664364-43-6)

Safety Data

• Hazardous Substances Data: 664364-43-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Cyano-1-naphthyl boronic acid is used as a reagent in organic synthesis for the formation of carbon-carbon and carbon-heteroatom bonds. Its ability to facilitate these bond formations makes it a crucial component in the synthesis of complex organic molecules.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 4-Cyano-1-naphthyl boronic acid is utilized as a precursor in the development of new drugs. Its unique properties allow for the creation of novel molecular structures with potential therapeutic applications.
Used in Agrochemical Production:
4-Cyano-1-naphthyl boronic acid is also employed in the agrochemical sector, where it serves as a building block for the synthesis of new pesticides and other agrochemicals, contributing to the development of more effective and environmentally friendly products.
Used in Materials Science:
In the field of materials science, 4-Cyano-1-naphthyl boronic acid is used as a component in the synthesis of advanced materials with specific properties. Its incorporation into these materials can lead to new applications in various industries, such as electronics, energy, and nanotechnology.

Upstream product

• 87700-65-0 4-bromo-1-naphthoic acid chloride 
• 16650-55-8 4-bromonaphthalene-1-carboxylic acid 
• 5419-55-6 Triisopropyl borate 
• 92616-49-4 4-bromonaphthalene-1-carbonitrile 

Relevant articles and documents

Process Development, Manufacture, and Understanding of the Atropisomerism and Polymorphism of Verinurad

The manufacturing route toward verinurad, an amphoteric, class II atropisomer that readily forms solvates, has proven to be highly complex. This previously required the isolation of intermediates with challenging physical properties and the application of cryogenic processes. New processes were designed and optimized, enabling the manufacture of 113 kg of verinurad in its desired polymorphic form. An interdisciplinary approach involving the synthesis, high-throughput experimentation, analytical chemistry, crystallization science, in silico modeling, and engineering was employed. Kinetic measurement of enantiomerically enriched verinurad salts confirmed that racemization occurred within the clearance time frame, thus mitigating safety concerns associated with inherent axial chirality in verinurad.

Significant rate enhancement via potassium pivalate in a Miyaura borylation approach to verinurad

We describe herein the significant rate-enhancing effect of employing potassium pivalate as a base in a Miyaura borylation. The manufacturing route to verinurad currently employs a Suzuki-Miyaura cross-coupling, requiring cryogenic conditions to generate the boronic acid coupling partner. This process has manufacturability challenges including those associated with low temperature operations and thus an alternative Miyaura borylation approach is described. High throughput screening was employed to investigate the effects of various carboxylate bases and their corresponding counterions on reactivity. Our results highlight potassium pivalate as producing exceptional rate acceleration. To the best of our knowledge this base has not previously been reported for use in Miyaura borylations. Diethanolamine transesterification is also reported as a facile and robust boronate isolation protocol. Successful application of this diethanolamine boronate ester in downstream cross-coupling chemistry has demonstrated the potential for this new route in commercial manufacture of verinurad.

Thiophene derivatives used as inhibitor of URAT1

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FUSED BENZENE DERIVATIVE AND USE

The present invention provides a compound represented by the general formula: [wherein Ring A represents an optionally substituted 5- to 8-membered ring, Ring B represents a further optionally substituted 4- to 10-membered ring, Ring C represents a further optionally substituted benzene ring, X1 represents carbon atom, X2 represents a carbon atom, an oxygen atom, etc., W represents a nitrogen atom, etc., Y11 represents a group represented by the formula CR2R3' (wherein R2 represents a hydrogen atom, a cyano group, a nitro group, etc., and R3' represents a hydrogen atom, a cyano group, a nitro group, etc., respectively), Y21 represents a group represented by the formula CR4R5' (wherein R4 represents a hydrogen atom, a cyano group, a nitro group, etc., and R5' represents a hydrogen atom, a cyano group, a nitro group, etc., respectively), etc., and R1 represents an electron-withdrawing group, respectively. The formula represents a single bond or a double bond] or a salt thereof, which is useful as an androgen receptor modulator.