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Cas Database

459-44-9

459-44-9

Identification

  • Product Name:p-TOLUENEDIAZONIUM FLUOROBORATE

  • CAS Number: 459-44-9

  • EINECS:

  • Molecular Weight:205.951

  • Molecular Formula: C7H7N2•BF4

  • HS Code:

  • Mol File:459-44-9.mol

Synonyms:4-methylbenzenediazonium tetrafluoroborate

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  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 61 Articles be found

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

Liras, Marta,Gonzalez-Bejar, Maria,Scaiano

, p. 9757 - 9762 (2010)

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

Liu, An-Di,Wang, Zhao-Li,Liu, Li,Cheng, Liang

, p. 16434 - 16447 (2021/11/16)

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.

Metal-Free Visible-Light Synthesis of Arylsulfonyl Fluorides: Scope and Mechanism

Louvel, Dan,Chelagha, Aida,Rouillon, Jean,Payard, Pierre-Adrien,Khrouz, Lhoussain,Monnereau, Cyrille,Tlili, Anis

supporting information, p. 8704 - 8708 (2021/05/17)

The first metal-free procedure for the synthesis of arylsulfonyl fluorides is reported. Under organo-photoredox conditions, aryl diazonium salts react with a readily available SO2 source (DABSO) to afford the desired product through simple nucleophilic fluorination. The reaction tolerates the presence of both electron-rich and -poor aryls and demonstrated a broad functional group tolerance. To shed the light on the reaction mechanism, several experimental techniques were combined, including fluorescence, NMR, and EPR spectroscopy as well as DFT calculations.

Azoacetylenes for the Synthesis of Arylazotriazole Photoswitches

Anderl, Felix,Balkenhohl, Moritz,Carreira, Erick M.,Fink, Moritz,Pfaff, Patrick

supporting information, p. 14495 - 14501 (2021/09/18)

We report a modular approach toward novel arylazotriazole photoswitches and their photophysical characterization. Addition of lithiated TIPS-acetylene to aryldiazonium tetrafluoroborate salts gives a wide range of azoacetylenes, constituting an underexplored class of stable intermediates.In situdesilylation transiently leads to terminal arylazoacetylenes that undergo copper-catalyzed cycloadditions (CuAAC) with a diverse collection of organoazides. These include complex molecules derived from natural products or drugs, such as colchicine, taxol, tamiflu, and arachidonic acid. The arylazotriazoles display near-quantitative photoisomerization and long thermalZ-half-lives. Using the method, we introduce for the first time the design and synthesis of a diacetylene platform. It permits implementation of consecutive and diversity-oriented approaches linking two different conjugants to independently addressable acetylenes within a common photoswitchable azotriazole. This is showcased in the synthesis of several photoswitchable conjugates, with potential applications as photoPROTACs and biotin conjugates.

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

Kurandina, Daria,Yadagiri, Dongari,Rivas, Monica,Kavun, Aleksei,Chuentragool, Padon,Hayama, Keiichi,Gevorgyan, Vladimir

supporting information, p. 8104 - 8109 (2019/06/13)

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.

Fluorosulfonylation of arenediazonium tetrafluoroborates with Na2S2O5 and N-fluorobenzenesulfonimide

Huang, Yangen,Liu, Shuai,Qing, Feng-Ling,Xu, Xiu-Hua

, (2020/10/18)

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.

Process route upstream and downstream products

Process route

C<sub>12</sub>H<sub>24</sub>O<sub>6</sub>*C<sub>7</sub>H<sub>7</sub>N<sub>2</sub><sup>(1+)</sup>*BF<sub>4</sub><sup>(1-)</sup>

C12H24O6*C7H7N2(1+)*BF4(1-)

18-crown-6 ether
17455-13-9

18-crown-6 ether

4-methylbenzenediazonium tetrafluoroborate
459-44-9

4-methylbenzenediazonium tetrafluoroborate

Conditions
Conditions Yield
In methanol; at 25 ℃; Equilibrium constant;
2C<sub>14</sub>H<sub>28</sub>O<sub>7</sub>*C<sub>7</sub>H<sub>7</sub>N<sub>2</sub><sup>(1+)</sup>*BF<sub>4</sub><sup>(1-)</sup>

2C14H28O7*C7H7N2(1+)*BF4(1-)

1,4,7,10,13,16,10-heptaoxacyclohenicosane
33089-36-0

1,4,7,10,13,16,10-heptaoxacyclohenicosane

4-methylbenzenediazonium tetrafluoroborate
459-44-9

4-methylbenzenediazonium tetrafluoroborate

Conditions
Conditions Yield
In CHCl2F; at -52.1 ℃; Thermodynamic data; rate constant; ΔGc(excit.);
tetrafluoroboric acid

tetrafluoroboric acid

4-methylbenzenediazonium tetrafluoroborate
459-44-9

4-methylbenzenediazonium tetrafluoroborate

Conditions
Conditions Yield
With sodium nitrite; In water; at -7 - 1 ℃; for 2h;
95%
tetrafluoroboric acid; p-toluidine; In ethanol; water; for 0.25h;
With sodium nitrite; In ethanol; water; at 0 ℃; for 1h;
94%
With sodium nitrite; In water; at 0 ℃; for 0.666667h; Inert atmosphere; Schlenk technique;
90%
With sodium nitrite; In water; for 0.166667h;
90.9%
With isopentyl nitrite; In ethanol; water; at -20 - 20 ℃; for 1h; Inert atmosphere;
82%
With sodium nitrite; In water; at 0 ℃; for 0.5h;
80%
With sodium nitrite; In water; at 0 ℃; for 0.75h; Schlenk technique;
78%
With sodium nitrite; In water; at 0 ℃; for 0.75h;
62%
tetrafluoroboric acid; p-toluidine; In water; at 0 ℃; for 0.5h;
With sodium nitrite; In water; for 0.5h;
17%
With sodium nitrite; In water;
With sodium nitrite; In water; at -5 - 0 ℃; for 0.666667h;
With sodium nitrite; In water; for 0.5h; Cooling with ice;
With sodium nitrite; In water; for 0.5h; Cooling with ice;
With tert.-butylnitrite; In ethanol; water; at 0 - 20 ℃; for 1h;
With sodium nitrite; In water; for 0.5h; Cooling with ice;
With tert.-butylnitrite; In ethanol; water; at 0 - 20 ℃; for 1h;
tetrafluoroboric acid; p-toluidine; In ethanol; water; at 20 ℃; for 0.0833333h;
With tert.-butylnitrite; In ethanol; water; at 0 ℃; for 2h; Inert atmosphere;
4-methylbenzenediazonium tetrafluoroborate
459-44-9

4-methylbenzenediazonium tetrafluoroborate

Conditions
Conditions Yield
With tetrafluoroboric acid; sodium nitrite; In water; at 0 ℃; for 0.5h;
97%
With tetrafluoroboric acid; sodium nitrite; In water; at 0 - 20 ℃;
95%
With tert.-butylnitrite; boron trifluoride diethyl etherate; In tetrahydrofuran; at -15 - 5 ℃; for 0.666667h;
92%
With tetrafluoroboric acid; sodium nitrite; In water; for 0.166667h; Cooling with ice;
91%
With tetrafluoroboric acid; sodium nitrite; In water;
82%
With tetrafluoroboric acid; sodium nitrite; at 0 ℃; for 1h;
65%
With nitrosonium tetrafluoroborate; In acetonitrile; at -40 ℃; for 1.5h; Inert atmosphere;
60%
With tetrafluoroboric acid; ethyl nitrite; In ethanol; at 0 ℃;
45%
With tetrafluoroboric acid; sodium nitrite; In water;
28%
With tetrafluoroboric acid; sodium nitrite;
With hydrogenchloride; tetrafluoroboric acid; sodium nitrite; at 0 ℃;
With tetrafluoroboric acid; sodium nitrite; at 0 - 5 ℃; for 0.5h;
With tert.-butylnitrite; boron trifluoride diethyl etherate; In diethyl ether; dichloromethane;
With tetrafluoroboric acid; sodium nitrite; In water; at 0 - 5 ℃; for 0.5h;
With tetrafluoroboric acid; sodium nitrite; In water;
p-toluidine; With hydrogenchloride; sodium nitrite; In water; at 5 - 10 ℃;
With sodium tetrafluoroborate; In water; Further stages.;
With tetrafluoroboric acid; sodium nitrite; In water; cooling;
With tetrafluoroboric acid; sodium nitrite; In water; at 0 - 5 ℃;
p-toluidine; With hydrogenchloride; sodium nitrite; Cooling;
With sodium tetrafluoroborate; In water;
With hydrofluoroboric acid; sodium nitrite; In water; at 0 ℃; for 0.583333h;
With tetrafluoroboric acid; sodium nitrite; In water; at 0 ℃; for 0.5h;
With tetrafluoroboric acid; sodium nitrite; In diethyl ether; water; at 0 ℃; for 0.5h;
With tetrafluoroboric acid; sodium nitrite; In water; at 0 ℃; for 1h;
With tetrafluoroboric acid; sodium nitrite; In water; at 0 - 5 ℃; for 0.5h; Inert atmosphere;
With tetrafluoroboric acid; sodium nitrite; In water; at 0 ℃; for 0.5h;
With tetrafluoroboric acid; sodium nitrite; In water; at 0 ℃; for 1.08333h; Sealed tube;
With tetrafluoroboric acid; sodium nitrite; In water; at 0 ℃; for 0.666667h;
With tetrafluoroboric acid; tert.-butylnitrite; In ethanol; water; at 0 - 20 ℃; for 1h;
With tetrafluoroboric acid; sodium nitrite; In water; at 0 ℃; for 0.5h;
With tetrafluoroboric acid; tert.-butylnitrite; In ethanol; water; at 0 - 20 ℃; for 0.5h;
sodium tetrafluoroborate
13755-29-8

sodium tetrafluoroborate

4-methylbenzenediazonium tetrafluoroborate
459-44-9

4-methylbenzenediazonium tetrafluoroborate

Conditions
Conditions Yield
p-toluidine; With hydrogenchloride; In water; at 0 - 5 ℃;
With sodium nitrite; In water;
sodium tetrafluoroborate; In water; at 5 ℃; for 0.166667h;
p-toluidine; With hydrogenchloride; In water; at 0 - 5 ℃;
With sodium nitrite; In water; at 0 - 10 ℃;
sodium tetrafluoroborate; In water; at 10 ℃; for 0.25h;
tetrafluoroboric acid

tetrafluoroboric acid

sodium nitrite
7632-00-0

sodium nitrite

4-methylbenzenediazonium tetrafluoroborate
459-44-9

4-methylbenzenediazonium tetrafluoroborate

Conditions
Conditions Yield
In water; at 0 ℃; for 0.5h;
84%
In water; at 0 - 5 ℃; for 0.5h;
76%
In water; at 5 ℃; Cooling with ice;
In water; at 0 - 20 ℃; for 0.5h;
tetrafluoroboric acid; p-toluidine; In water; at 0 ℃; for 0.25h;
sodium nitrite; In water; at 0 ℃; for 0.5h;
boron trifluoride diethyl etherate
109-63-7

boron trifluoride diethyl etherate

4-methylbenzenediazonium tetrafluoroborate
459-44-9

4-methylbenzenediazonium tetrafluoroborate

Conditions
Conditions Yield
With tert.-butylnitrite; In dichloromethane; at 0 - 20 ℃; for 2h;
With tert.-butylnitrite; In dichloromethane; for 1.16667h; Inert atmosphere;
17 g
nitrosonium tetrafluoroborate

nitrosonium tetrafluoroborate

4-methylbenzenediazonium tetrafluoroborate
459-44-9

4-methylbenzenediazonium tetrafluoroborate

Conditions
Conditions Yield
In ethyl acetate; at 0 ℃; for 1h; Inert atmosphere;
tetrafluoroboric acid

tetrafluoroboric acid

tert.-butylnitrite
540-80-7

tert.-butylnitrite

4-methylbenzenediazonium tetrafluoroborate
459-44-9

4-methylbenzenediazonium tetrafluoroborate

Conditions
Conditions Yield
In ethanol; at 0 - 20 ℃; for 1h; Inert atmosphere;
87%
4-chloro-aniline
106-47-8

4-chloro-aniline

4-methylbenzenediazonium tetrafluoroborate
459-44-9

4-methylbenzenediazonium tetrafluoroborate

Conditions
Conditions Yield
With tetrafluoroboric acid; sodium nitrite; In water; at -3 ℃;

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