Benzenediazonium tetrafluoroborate
Phenyldiazonium tetrafluoroborate · Ccris 5461 · Sildenafil Impurity 44 · Benzenediazonium fluoborate · Benzenediazonium fluoroborate · Diazobenzene tetrafluoroborate · Phenyldiazonium fluoborate (salt) · Benzenediazonium,tetrafluoroborate
Identifiers & Physical Properties
| CAS No. | 369-57-3 |
|---|---|
| Molecular formula | C6H5BF4N2 |
| Average molar mass | 191.92 g/mol |
| Monoisotopic mass | 192.048191 g/mol |
| SMILES | F[B-](F)(F)F.N#[N+]c1ccccc1 |
| InChIKey | JNCLVGMBRSKDED-UHFFFAOYSA-N |
| PubChem CID | 5284485 |
| EC No. | 820-352-6 |
| DTXSID | DTXSID5021467 |
Chemical & Physical Properties
| Topological polar surface area | 28.2 |
|---|---|
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 6 |
| Rotatable bonds | 0 |
| Heavy atoms | 13 |
| Formal charge | 0 |
| Complexity | 124 |
| Melting point | 121-122 °C (decomp) |
| Density | 1.53 g/cm3(Temp: 25 °C) |
| Solubility | fairly sol polar solvents such as acetonitrile, acetone, pyridine, DMF, DMSO, and HMPA with decompositionslightly sol waterinsol hydrocarbons and Et2Osolubilized in nonpolar media by crown ethers. |
| Color | colorless solid after recrystallizationturns pink at 80 °C |
| EWG's Food Scores | 1 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H335-H302-H319-H315 |
| GHS precautionary statements | P264-P270-P301+P312-P330-P501-P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P |
| Toxicity | mmo-sat 10 mmol/L CNREA8 42,1446,82 |
Safety & Regulations
| GHS classification | DangerH228 (66.7%): Flammable solid [Danger Flammable solids]H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]H373 (33.3%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]P210, P240, P241, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazards summary | Causes dermatitis in oral and subcutaneous lethal-dose studies of hamsters[RTECS] See Diazobenzenesulfonic acid. See 4-Nitrobenzenediazonium tetrafluoroborate. See Potassium tetrafluoroborate. |
| Hazard Classes and Categories | Flam. Sol. 1 (66.7%)Acute Tox. 4 (100%)Skin Irrit. 2 (100%)Eye Irrit. 2 (100%)STOT SE 3 (100%)STOT RE 2 (33.3%) |
| Toxicity | mmo-sat 10 mmol/L CNREA8 42,1446,82 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| GHS hazard statements | H335-H302-H319-H315 |
| GHS precautionary statements | P264-P270-P301+P312-P330-P501-P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P |
Applications & Uses
Uses
Benzenediazonium Tetrafluoroborate is much higher stability than the corresponding chlorides; shock-insensitive; often used when pure, isolated arenediazonium salts are needed; reagent for introducing aryl, arylazo, arylhydrazono, or amino groups; forms fluoroarenes upon heating; building block for heterocycles.
Preparation & Synthesis
Preparation
Preparative Methods of Benzenediazonium Tetrafluoroborate: The most commonly used procedures consist in diazotization of an aromatic amine (ArNH2) with NaNO2 in aqueous HCl or H2SO4 followed by precipitation of the salt with added NaBF4 or fluoroboric acid. Alternatively, the diazotization can be carried out directly in 40-50% aqueous HBF4. Aromatic amines that do not dissolve in aqueous mineral acids can be reacted with NO+BF4 - in an anhydrous organic solvent or in liquid SO2. This method can also be applied to N-(trimethylsilyl)anilines and for the preparation of those salts that are not easily isolated from water. An improved, high-yielding one-pot procedure employs ArNH2, t-BuONO, and BF3. Et2O in an anhydrous organic solvent, typically CH2Cl2.