28912-93-8

Basic information

• Product Name: naphthalene-1-diazonium tetrafluoroborate
• Synonyms: naphthalene-1-diazonium tetrafluoroborate
• CAS NO: 28912-93-8
• Molecular Formula: BF₄*C₁₀H₇N₂
• Molecular Weight: 241.9805928
• EINECS: 249-308-9
• Mol File: 28912-93-8.mol
• Article Data: 14

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: naphthalene-1-diazonium tetrafluoroborate(CAS DataBase Reference)
• NIST Chemistry Reference: naphthalene-1-diazonium tetrafluoroborate(28912-93-8)
• EPA Substance Registry System: naphthalene-1-diazonium tetrafluoroborate(28912-93-8)

Safety Data

• Hazardous Substances Data: 28912-93-8(Hazardous Substances Data)

Usage

Uses

1-Naphthyldiazonium Tetrafluoroborate is used in the preparation of alkylaryl asymmetrical azo compound.

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 
• 7632-00-0 sodium nitrite 
• 540-80-7 tert.-butylnitrite 

Downstream Products

• 321-38-0 1-Fluoronaphthalene 
• 86-55-5 1-naphthalenecarboxylic acid 
• 2653-64-7 1-(2'-hydroxynaphthylazo)naphthalene 
• 90-13-1 1-Chloronaphthalene 
• 1778-72-9 (E)-1-(2,6-dimethyl-4-hydroxyphenylazo)naphthalene 
• 5023-64-3 1-(benzylsulfanyl)naphthalene 
• 73368-15-7 benzoic acid-[1]naphthoic acid-anhydride 
• 605-85-6 1-(1-naphthyl)-2-phenylethanone 
• 886361-18-8 perfluorophenyl naphthalene-1-sulfonate 
• 317-55-5 naphthalene-1-sulfonyl fluoride 
• 4044-57-9 1-phenylethynyl-naphthalene 
• 605-02-7 1-phenylnaphthalene 

Relevant articles and documents

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

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.

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.).