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| | 4-FLUOROBENZOYLACETONITRILE Basic information |
| Product Name: | 4-FLUOROBENZOYLACETONITRILE | | Synonyms: | P-FLUOROBENZOYLACETONITRILE;AKOS B020924;3-(4-FLUORO-PHENYL)-3-OXO-PROPIONITRILE;3-(4'-FLUOROPHENYL)-3-OXOPROPANENITRILE;ART-CHEM-BB B020924;BUTTPARK 34\07-91;4-FLUOROBENZOYLACETONITRILE;3-(4-Fluorophenyl)-3-oxopropanenitrile, 3-(4-Fluorophenyl)-3-oxopropionitrile | | CAS: | 4640-67-9 | | MF: | C9H6FNO | | MW: | 163.15 | | EINECS: | 627-421-8 | | Product Categories: | HALIDE;4640-67-9 | | Mol File: | 4640-67-9.mol |  |
| | 4-FLUOROBENZOYLACETONITRILE Chemical Properties |
| Melting point | 84-88 °C | | Boiling point | 311.9±22.0 °C(Predicted) | | density | 1+-.0.06 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | solubility | Soluble in dimethylformamide, dimethyl sulfoxide. | | pka | 7.67±0.10(Predicted) | | form | Solid | | color | Yellow | | λmax | 247nm(EtOH)(lit.) | | InChI | InChI=1S/C9H6FNO/c10-8-3-1-7(2-4-8)9(12)5-6-11/h1-4H,5H2 | | InChIKey | LOJBBLDAJBJVBZ-UHFFFAOYSA-N | | SMILES | C1(=CC=C(F)C=C1)C(=O)CC#N | | CAS DataBase Reference | 4640-67-9(CAS DataBase Reference) |
| Hazard Codes | Xi,Xn | | Risk Statements | 36/37/38-22 | | Safety Statements | 26-36/37/39 | | WGK Germany | 3 | | Hazard Note | Irritant | | HazardClass | 6.1 | | HS Code | 29269090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 4-FLUOROBENZOYLACETONITRILE Usage And Synthesis |
| Chemical Properties | White to light brown solid | | Uses | 4-Fluorobenzoylacetonitrile is used as a reagent in the synthesis of Blonanserin (B595850); a 5-HT2 serotonin receptor and D2 dopamine receptor antagonist, used as an antipsychotic. 4-Fluorobenzoylacetonitrile is also used in the preparation of pyrazolopyrimidines as potential antimicrobial and antioxidant agents. | | Synthesis | The general procedure for the synthesis of 4-fluorobenzoylacetonitrile from methyl 4-fluorobenzoate and acetonitrile was as follows: methyl 4-fluorobenzoate (29.44 kg), toluene (177 L), and acetonitrile (59 L; 5.9 mole equivalents relative to methyl 4-fluorobenzoate) were added to a reactor. The reaction mixture was cooled to -5 to 0°C. A solution of sodium bis(trimethylmethylsilyl)amide (NaHMDS, 40% in THF) (192 L; 2 molar equivalents relative to methyl 4-fluorobenzoate) was slowly added while maintaining the temperature between -5 and +5 °C. The addition line was flushed with toluene (9 L) to ensure complete transfer. The reaction mixture was quenched by the addition of dilute hydrochloric acid while maintaining a temperature between -5 and +25°C. Continue to add acid until the pH falls below 5. Separate the layers and discard the lower aqueous layer. A small amount of solvent was removed by vacuum distillation. Toluene (59 L) was added and the mixture was heated to 85 to 90 °C to obtain a homogeneous solution. The mixture was cooled to 50 to 55 °C and n-heptane (29 L) was added to induce precipitation. The mixture was further cooled to 20 to 25 °C and the solid product was isolated by filtration and washed with n-heptane (59L). The wet product was dried under vacuum at 40 to 45°C to give 4-fluorobenzoylacetonitrile (26 kg, 83% yield) with 98.7% GC purity. The main impurity, 4-methoxybenzoylacetonitrile, was present in 0.03% (% GC area). | | References | [1] Patent: JP2018/43989, 2018, A. Location in patent: Paragraph 0124-0131 |
| | 4-FLUOROBENZOYLACETONITRILE Preparation Products And Raw materials |
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