| Identification | More | [Name]
4-FLUOROBENZOYLACETONITRILE | [CAS]
4640-67-9 | [Synonyms]
3-(4'-FLUOROPHENYL)-3-OXOPROPANENITRILE
3-(4-FLUOROPHENYL)-3-OXOPROPANENITRILE
3-(4-FLUORO-PHENYL)-3-OXO-PROPIONITRILE
4-FLUOROBENZOYLACETONITRILE
AKOS B020924
ART-CHEM-BB B020924
BUTTPARK 34\07-91
P-FLUOROBENZOYLACETONITRILE
4-FLUOROBENZOYLACETONITRILE 96%
3-Oxo-3-(4-fluorophenyl)propionitrile, 4-Fluoro-μ-oxobenzenepropanenitrile, 4-Fluorophenacyl cyanide
4-Fluorobenzoylacetonitrile ,98.0% | [EINECS(EC#)]
627-421-8 | [Molecular Formula]
C9H6FNO | [MDL Number]
MFCD00662062 | [Molecular Weight]
163.15 | [MOL File]
4640-67-9.mol |
| Chemical Properties | Back Directory | [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. | [form ]
Solid | [pka]
7.67±0.10(Predicted) | [color ]
Yellow | [λmax]
247nm(EtOH)(lit.) | [Detection Methods]
HPLC | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [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 |
| Hazard Information | Back Directory | [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 |
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