28912-93-8

Usage

Uses

Used in Chemical Synthesis:
Naphthalene-1-diazonium tetrafluoroborate is used as a synthetic intermediate for the preparation of alkylaryl asymmetrical azo compounds. These azo compounds are important in the production of dyes, pigments, and other organic compounds due to their unique color and chemical properties.
Used in Dye and Pigment Production:
In the dye and pigment industry, naphthalene-1-diazonium tetrafluoroborate is used as a key component in the synthesis of various dyes and pigments. The resulting azo compounds contribute to the vibrant colors and stability of these products, making them suitable for a wide range of applications, including textiles, plastics, and printing inks.
Used in Research and Development:
Naphthalene-1-diazonium tetrafluoroborate is also utilized in research and development for the study of chemical reactions and mechanisms involving diazonium compounds. Its reactivity and versatility make it a valuable tool for chemists in understanding and developing new synthetic pathways and applications for azo compounds and related materials.

InChI:InChI=1/C10H7N2.BF4/c11-12-10-7-3-5-8-4-1-2-6-9(8)10;2-1(3,4)5/h1-7H;/q+1;-1

Upstream product

• 134-32-7 1-amino-naphthalene 
• 540-80-7 tert.-butylnitrite 
• 7632-00-0 sodium nitrite 

Downstream Products

• 321-38-0 1-Fluoronaphthalene 
• 826-74-4 1-vinylnaphthalene 
• 86-55-5 1-naphthalenecarboxylic acid 
• 73368-15-7 benzoic acid-[1]naphthoic acid-anhydride 
• 91-20-3 naphthalene 
• 119286-02-1 S-naphthalen-1-yl ethanethioate 
• 529-36-2 1-Naphthalenethiol 
• 24197-75-9 4-cyanophenyl thiolbenzoate 
• 7570-98-1 1-naphthyl phenyl sulfide 
• 2653-64-7 1-(2'-hydroxynaphthylazo)naphthalene 
• 1778-72-9 (E)-1-(2,6-dimethyl-4-hydroxyphenylazo)naphthalene 
• 605-02-7 1-phenylnaphthalene 
• 86-57-7 1-Nitronaphthalene 
• 2653-72-7 1-(1-naphthylazo)-4-hydroxynaphthalene 

Relevant academic research and scientific papers

Stability of 1-naphthalenediazonium ion in solution. Complexation and decomposition of 1-naphthalenediazonium tetrafluoroborate in the presence of crown ethers and acyclic polyethers in 1,2-dichloroethane and the gas phase under fast atom bombardment conditions

The effects of solvent, temperature and pH on the rate of decomposition of uncomplexed 1-naphthalenediazonium tetrafluoroborate were studied by UV spectrometry. The complexation of the 1-naphthalenediazonium ion with crown ethers containing 4-10 oxygen atoms and some acyclic polyethers was detected and characterized in the gas phase by fast atom bombardment mass spectrometry (FAB-MS). In addition, the host-guest complexation and the kinetics of the thermal dediazoniation of 1-naphthalenediazonium ion in the presence of four crown ethers and two acyclic polyethers were studied in 1,2-dichloroethane (DCE) solution at 40 °C by UV spectrometry. All hosts, except 12-crown-4, formed 1:1 complexes under FAB conditions. The values of the thermodynamic stability K and the stabilizing ability of the complexation (k2/k1) in DCE were calculated from the kinetic data. The thermodynamic and kinetic stabilities were observed to be greater for the inclusion complex of the 1-naphthalenediazonium ion formed with crown ethers containing at least six oxygen atoms than for the non-spesific adduct formation formed with 15-crown-5. This was also true for tetraglyme, whose chain is too short to be capable of being fully wrapped around the diazonium group as in the complex of PEG 1000. Crown ethers with seven oxygen atoms are the strongest complexing agents for all the aromatic diazonium ions studied, for the 1-naphthalenediazonium ion investigated here and for arenediazonium ions examined earlier. The values of the activation enthalpy ΔH≠ for the thermal dediazoniation of the uncomplexed salt in both the acidic aqueous solution and DCE were observed to be high, and the corresponding values of activation entropy ΔS≠ were clearly positive. The results are consistent with a heterolytic SNI-like mechanism involving the decomposition of the uncomplexed and complexed 1-naphthalenediazonium ion into a highly reactive naphthyl cation, followed by fast product-determining reactions with nucleophiles to give the products. Copyright

Aryl Diazonium Salts: Powerful Arylating Agents for Catellani-Typeortho-Arylation

The Catellani reaction provides an efficient synthetic approach to polyfunctionalized arenes. However, the selectiveortho-arylating reagents employed in these reactions have been strictly limited to activated bromoarenes. As demonstrated in this work, aryl diazonium salts bearing both electron-donating and electron-withdrawing substituents, after in situ transformations with KI into the corresponding iodoarenes, were efficient arylating reagents for Catellani typeortho-arylation approaches.

Fluorosulfonylation of arenediazonium tetrafluoroborates with Na2S2O5 and N-fluorobenzenesulfonimide

A transition-metal-free Sandmeyer-type fluorosulfonylation reaction has been achieved by the three-component reaction of arenediazonium tetrafluoroborates, Na2S2O5, and N-fluorobenzenesulfonimide (NFSI). The reaction proceeds through a radical tandem process, affording various arenesulfonyl fluorides in moderate to high yields. This protocol not only provides a complement to the previous fluorosulfonylation reactions, but also extends the applications of Sandmeyer reaction.

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.

Electrochemical Cross-Coupling of C(sp2)?H with Aryldiazonium Salts via a Paired Electrolysis: an Alternative to Visible Light Photoredox-Based Approach

Photoredox-based C?H bond functionalization constitutes one of the most powerful and atom-economical approaches to organic syntheses. During this type of reaction, single electron transfer takes place between the photocatalyst (PC) and redox- active substrates. Electrosynthesis also involves electron transfer between substrates and electrodes. In this paper, we focus upon electrochemical cross-coupling of C(sp2)?H with aryldiazonium salts and have developed an efficient electrochemical approach to the Minisci-type arylation reaction. The constant current paired electrosynthesis proceeds in a simple undivided cell without external supporting electrolyte, features a wide range of substrates and is easy to scale-up. These results demonstrate that photoredox-based cross-coupling of C(sp2)?H with aryldiazonium salts can also proceed successfully under paired electrolysis conditions, thereby contributing to understanding of the parallels between photosynthesis and electrosynthesis. (Figure presented.).

Pentafluoroethylation of Arenediazonium Tetrafluoroborates Using On-Site Generated Tetrafluoroethylene

Copper-mediated pentafluoroethylation of arenediazonium tetrafluoroborates with tetrafluoroethylene (TFE) on-site generated from TMSCF3 has been developed as a new method to prepare pentafluoroethyl arenes. The active pentafluoroethylation reagent “CuC2F5” is pre-generated from CuSCN, TFE and CsF, and its generation and further reaction are strongly solvent-dependent. This pentafluoroethylation reaction represents the first example of Sandmeyer-type pentafluoroethylation, which exhibits good functional group tolerance and potential applications for the synthesis of complicated bioactive compounds.

Additions to N-Sulfinylamines as an Approach for the Metal-free Synthesis of Sulfonimidamides: O-Benzotriazolyl Sulfonimidates as Activated Intermediates

Sulfonimidamides are obtained in moderate to very good yields from the key intermediates O-benzotriazolyl sulfonimidates, which are formed by reacting aryldiazonium tetrafluoroborates, N-tritylsulfinylamine, and N-hydroxybenzotriazole hydrate in a process mediated by a tertiary amine. The formation of the sulfonimidate proceeds in inexpensive and environmentally benign dimethyl carbonate as the solvent, it does not require anhydrous conditions, and the product yields generally exceed 70 %. The substrate scope is broad, and a wide range of sensitive organic functionalities is well tolerated. The reactions probably proceed via aryl radicals formed from diazonium cations with assistance from both the tertiary amine and the sulfinylamine.

Hypervalent Iodine(III)-Catalyzed Balz–Schiemann Fluorination under Mild Conditions

An unprecedented hypervalent iodine(III) catalyzed Balz–Schiemann reaction is described. In the presence of a hypervalent iodine compound, the fluorination reaction proceeds under mild conditions (25–60 °C), and features a wide substrate scope and good functional-group compatibility.

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.

Cobalt bis(acetylacetonate)–tert-butyl hydroperoxide–triethyl-silane: A general reagent combination for the Markovnikov-selective hydrofunctionalization of alkenes by hydrogen atom transfer

We show that cobalt bis(acetylacetonate) [Co(acac)2], tert-butyl hydroperoxide (TBHP), and triethylsilane (Et3SiH) constitute an inexpensive, general, and practical reagent combination to initiate a broad range of Markovnikov-selective alkene hydrofunctionalization reactions. These transformations are believed to proceed by cobalt-mediated hydrogen atom transfer (HAT) to the alkene substrate, followed by interception of the resulting alkyl radical intermediate with a SOMOphile. In addition, we report the first reductive couplings of unactivated alkenes and aryldiazonium salts by an HAT pathway. The simplicity and generality of the Co(acac)2–TBHP–Et3SiH reagent combination suggests it as a useful starting point to develop HAT reactions in complex settings.