456-39-3

Usage

Uses

Used in Organic Synthesis:
3-Chlorobenzenediazonium tetrafluorborate is used as a diazonium salt for the formation of azo compounds in organic synthesis reactions.
Used in Pharmaceutical Industry:
3-Chlorobenzenediazonium tetrafluorborate is used as a precursor for the synthesis of various aromatic and heteroaromatic compounds, as well as in the development of new materials and pharmaceuticals.
Used in Material Science:
3-Chlorobenzenediazonium tetrafluorborate is used as a precursor in the development of new materials.
Note: Due to its reactivity, handling and storage of 3-chlorobenzenediazonium tetrafluorborate should be done with caution, as it can be explosive and potentially toxic if mishandled.

InChI:InChI=1/C6H4ClN2.BF4/c7-5-2-1-3-6(4-5)9-8;2-1(3,4)5/h1-4H;/q+1;-1

Upstream product

• 100-77-6 3-chlorobenzenediazonium chloride 
• 108-42-9 3-chloro-aniline 
• 13755-29-8 sodium tetrafluoroborate 
• 109-63-7 boron trifluoride diethyl etherate 
• 540-80-7 tert.-butylnitrite 
• 7632-00-0 sodium nitrite 

Downstream Products

• 13031-39-5 3-chlorophenyl acetate 
• 2051-61-8 m-chlorobiphenyl 
• 106131-20-8 (E)-1,2-bis(3-chlorophenyl)diazene 
• 2050-67-1 PCB 11 
• 446836-14-2 C₁₁H₁₀ClNO₂S 
• 108-37-2 1-bromo-3-chlorobenzene 
• 63686-33-9 [Ir(CO)Cl(NH:NC₆H₃Cl-m)(PPh₃)2]BF₄ 
• 108-90-7 chlorobenzene 
• 105230-62-4 (3-chlorophenyl)(phenyl)selane 
• 541-73-1 1,3-Dichlorobenzene 
• 38527-57-0 2-(m-chlorophenyl)furan 
• 14123-60-5 3-chlorophenylacetone 
• 1184248-07-4 1-(3-chlorophenyl)-2-phenylpropan-2-ol 
• 5097-96-1 bis(m-chlorophenyl) sulfide 

Relevant academic research and scientific papers

Aqueous and Visible-Light-Promoted C-H (Hetero)arylation of Uracil Derivatives with Diazoniums

Direct C5 (hetero)arylation of uracil and uridine substrates with (hetero)aryl diazonium salts under photoredox catalysis with blue light was reported. The coupling proceeds efficiently with diazonium salts and heterocycles in good functional group tolerance at room temperature in aqueous solution without transition-metal components. A plausible radical mechanism has been proposed.

Comparison of the Thermal Stabilities of Diazonium Salts and Their Corresponding Triazenes

A range of diazonium salts and their corresponding triazenes have been prepared in order to directly compare their relative thermal stabilities (via initial decomposition temperature) from differential scanning calorimetry (DSC) data. A structure-stability relationship has been explored to investigate trends in stability, depending on the aromatic substituent and the structure of the secondary amine component of the diazonium salts and triazenes. All of the triazenes investigated show significantly greater stability (many are stable above 200 °C) compared with the corresponding diazonium salts, which show varying stabilities.

Copper-mediated tandem ring-opening/cyclization reactions of cyclopropanols with aryldiazonium salts: Synthesis of: N -arylpyrazoles

A general method for the synthesis of structurally diverse N-arylpyrazoles from readily available cyclopropanols and aryldiazonium salts is disclosed. The reaction was conducted at room temperature within minutes with a broad substrate scope and excellent regioselectivity.

Discovery and structure-activity relationship studies of 1-aryl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as potent dual inhibitors of indoleamine 2,3-dioxygenase 1 (IDO1) and trytophan 2,3-dioxygenase (TDO)

Indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO), which mediate kynurenine pathway of tryptophan degradation, have emerged as potential new targets in immunotherapy for treatment of cancer because of their critical role in immunosuppression in the tumor microenvironment. In this investigation, we report the structural optimization and structure-activity relationship studies of 1-phenyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as a new class of IDO1/TDO dual inhibitors. Among all the obtained dual inhibitors, 1-(3-chloro-4-fluorophenyl)-6-fluoro-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione (38) displayed the most potent IDO1 and TDO inhibitory activities with IC50 (half-maximal inhibitory concentration) values of 5 nM for IDO1 and 4 nM for TDO. It turned out that compound 38 was not a PAINS compound. Compound 38 could efficiently inhibit the biofunction of IDO1 and TDO in intact cells. In LL2 (Lewis lung cancer) and Hepa1-6 (hepatic carcinoma) allograft mouse models, this compound also showed considerable in vivo anti-tumor activity and no obvious toxicity was observed. Therefore, 38 could be a good lead compound for cancer immunotherapy and deserving further investigation.

Transition-Metal- A nd Light-Free Directed Amination of Remote Unactivated C(sp3)-H Bonds of Alcohols

Due to the great value of amino alcohols, new methods for their synthesis are in high demand. Abundant aliphatic alcohols represent the ideal feedstock for the method development toward this important motif. To date, transition-metal-catalyzed approaches for the directed remote amination of alcohols have been well established. Yet, they have certain disadvantages such as the use of expensive catalysts and limited scope. Very recently, transition-metal-free visible-light-induced radical approaches have emerged as new powerful tools for directed remote amination of alcohols. Relying on 1,5-HAT reactivity, these methods are limited to β-or δ- A mination only. Herein, we report a novel transitionmetal- A nd visible-light-free room-temperature radical approach for remote β-, γ-, and δ-C(sp3)-N bond formation in aliphatic alcohols using mild basic conditions and readily available diazonium salt reagents.

Modular and Selective Arylation of Aryl Germanes (C?GeEt3) over C?Bpin, C?SiR3 and Halogens Enabled by Light-Activated Gold Catalysis

Selective C (Formula presented.) –C (Formula presented.) couplings are powerful strategies for the rapid and programmable construction of bi- or multiaryls. To this end, the next frontier of synthetic modularity will likely arise from harnessing the coupling space that is orthogonal to the powerful Pd-catalyzed coupling regime. This report details the realization of this concept and presents the fully selective arylation of aryl germanes (which are inert under Pd0/PdII catalysis) in the presence of the valuable functionalities C?BPin, C?SiMe3, C?I, C?Br, C?Cl, which in turn offer versatile opportunities for diversification. The protocol makes use of visible light activation combined with gold catalysis, which facilitates the selective coupling of C?Ge with aryl diazonium salts. Contrary to previous light-/gold-catalyzed couplings of Ar–N2+, which were specialized in Ar–N2+ scope, we present conditions to efficiently couple electron-rich, electron-poor, heterocyclic and sterically hindered aryl diazonium salts. Our computational data suggest that while electron-poor Ar–N2+ salts are readily activated by gold under blue-light irradiation, there is a competing dissociative deactivation pathway for excited electron-rich Ar–N2+, which requires an alternative photo-redox approach to enable productive couplings.

RhIII-Catalyzed Synthesis of Highly Substituted 2-Pyridones using Fluorinated Diazomalonate

A RhIII-catalyzed strategy was developed for the rapid construction of highly substituted 2-pyridone scaffolds using α,β-unsaturated oximes and fluorinated diazomalonate. The reaction proceeds through direct, site-selective alkylation based on migratory insertion and subsequent cyclocondensation. A wide substrate scope with different functional groups was explored. The requirement of fluorinated diazomalonate was explored for this transformation. The developed methodology was further extended with the synthesis of the bioactive compound.

Photocatalyzed borylation using water-soluble quantum dots

The synthesis of arylboronates by Sandmeyer-type reactions in the presence of water still remains a significant challenge. Herein, we report the use of water-soluble MPA-capped quantum dot (QD) photocatalysts for the borylation of diazonium salts in the presence of water. A biphasic system under mild acidic conditions remains critical to prevent decomposition and competitive disulphide bond formation. The present protocol offers a broader scope of substrates and borylating agents. Additionally, this catalytic system offers a significantly high turnover number (TON). The present methodology can effectively distinguish subtle reactivity differences between boronic acids and boronates. Mechanistic investigation suggests an excited-state electron transfer pathway.

Palladium catalyzed stereocontrolled synthesis of C-aryl glycosides using glycals and arenediazonium salts at room temperature

A stereocontrolled synthesis of aryl-C-glycosides was achieved using glycals and aryldiazonium salts in the presence of palladium acetate. A wide range of glycals including d-glucal, d-galactal, l-rhamnal, d-xylal and d-ribal underwent C-arylation at the anomeric carbon in the presence of different aryldiazonium tetrafluoroborates and gave synthetically useful 2,3-deoxy-3-keto-α-aryl-C-glycosides in good to excellent yields. Broad substrate scope, simple operation and room temperature reactions make this protocol very attractive in organic synthesis.

Copper-Catalyzed Arylsulfonylation and Cyclizative Carbonation of N-(Arylsulfonyl)acrylamides Involving Desulfonative Arrangement toward Sulfonated Oxindoles

Sulfonated oxindoles are accessed by a Cu(OAc)2-catalyzed three-component reaction of N-(arylsulfonyl)acrylamides, DABSO, and aryldiazonium tetrafluoroborates. This transformation is triggered by the formation of arylsulfonyl radicals in situ from the reaction of aryldiazonium tetrafluoroborates and DABSO. Afterward, the sequential radical addition, radical cyclization, and desulfonylative 1,4-aryl migration take place to provide the final product by the formation of four new bonds in one pot. This procedure shows good functional group tolerance.