459-44-9

Basic information

• Product Name: 4-methylbenzenediazonium tetrafluoroborate
• Synonyms: 4-methylbenzenediazonium tetrafluoroborate;p-Toluenediazonium·tetrafluoroborate;4-toluenediazonium tetrafluoroborate
• CAS NO: 459-44-9
• Molecular Formula: BF₄*C₇H₇N₂
• Molecular Weight: 205.9484928
• EINECS: 207-289-4
• Mol File: 459-44-9.mol
• Article Data: 61

Chemical Properties

• Melting Point: 109-111 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: 4-methylbenzenediazonium tetrafluoroborate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methylbenzenediazonium tetrafluoroborate(459-44-9)
• EPA Substance Registry System: 4-methylbenzenediazonium tetrafluoroborate(459-44-9)

Safety Data

• Hazardous Substances Data: 459-44-9(Hazardous Substances Data)

Usage

General Description

4-methylbenzenediazonium tetrafluoroborate is a chemical compound that is commonly used in organic synthesis and as a reagent in various reactions. It is a tetrafluoroborate salt of the diazonium cation derived from 4-methyl aniline. The compound is highly reactive and unstable, and must be handled with care due to its potential explosive nature. It is often used in the preparation of aryl fluorides and other aromatic compounds through the process of diazonium coupling reactions. Additionally, 4-methylbenzenediazonium tetrafluoroborate has also been studied for its potential use in the development of new materials and pharmaceuticals.

InChI:InChI=1/C7H7N2.BF4/c1-6-2-4-7(9-8)5-3-6;2-1(3,4)5/h2-5H,1H3;/q+1;-1

Upstream product

• 106-49-0 p-toluidine 
• 540-80-7 tert.-butylnitrite 
• 109-63-7 boron trifluoride diethyl etherate 
• 13755-29-8 sodium tetrafluoroborate 
• 7632-00-0 sodium nitrite 
• 106-47-8 4-chloro-aniline 

Downstream Products

• 17113-32-5 2-(4-methylphenyl)furan 
• 33269-11-3 3-(p-Methylphenylazo)-indol 
• 94144-23-7 2-p-Tolyl-4-p-tolylsulfanyl-5,6-dihydro-2H-2aλ⁴,3-dithia-1,2-diaza-cyclopenta[cd]pentalene 
• 352-32-9 p-fluorotoluene 
• 29540-83-8 p-tolyl triflate 
• 624-31-7 4-tolyl iodide 
• 236736-28-0 hexafluoro-1,2-diphenylcyclobutane 
• 128346-36-1 C₃₀H₂₄F₆ 
• 78795-69-4 C₁₃H₁₁Cl₂FTe 
• 115197-99-4 C₂₁H₁₉NS₂ 
• 119-61-9 benzophenone 
• 611-97-2 bis(p-methylphenyl)-methanone 
• 134-84-9 4-Methylbenzophenone 
• 116888-07-4 2-tert-Butyl-1-(4-methylphenylhydrazono)-1H-isoindolium-tetrafluoroborat 

Relevant articles and documents

On-off QD switch that memorizes past recovery from quenching by diazonium salts

The understanding of the interaction of CdSe/ZnS semiconductor quantum dots (QD) with their chemical environment is fundamental, yet far from being fully understood. p-Methylphenyldiazonium tetrafluoroborate has been used to get some insight into the effect of diazonium salts on the spectroscopy of QD. Our study reveals that the surface of CdSe/ZnS quantum dots can be modified by diazonium salts (although not functionalized), showing and on-off fluorescence behaviour that memorizes past quenching recoveries. Facile modification of the surface confers protection against quenching by new molecules of diazonium salt and other known quenchers such as 4-amino-TEMPO. The reaction mechanism has been explored in detail by using different spectroscopic techniques. At the first time after addition of diazonium salt over QD the fluorescent is turned off with Stern-Volmer behaviour; the fluorescence recovers following irradiation. Subsequent additions of diazonium salts do not cause the same degree of quenching. We have noted that the third addition (following two cycles of addition and irradiation) is unable to quench the fluorescence. Monitoring the process using NMR techniques reveals the formation of p-difluoroborane toluene as a result of the irradiation of diazonium-treated QD; the treatment leads to the fluorination of the QD surface.

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.

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.