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| | 3-Fluorophenylacetonitrile Basic information |
| | 3-Fluorophenylacetonitrile Chemical Properties |
| Melting point | 21 °C | | Boiling point | 113-114 °C18 mm Hg(lit.) | | density | 1.163 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.502(lit.) | | Fp | >230 °F | | storage temp. | Sealed in dry,Room Temperature | | form | powder to lump to clear liquid | | color | White or Colorles to Yellow to Orange | | Specific Gravity | 1.163 | | BRN | 1861071 | | Exposure limits | NIOSH: IDLH 25 mg/m3 | | InChI | InChI=1S/C8H6FN/c9-8-3-1-2-7(6-8)4-5-10/h1-3,6H,4H2 | | InChIKey | DEJPYROXSVVWIE-UHFFFAOYSA-N | | SMILES | C1(CC#N)=CC=CC(F)=C1 | | CAS DataBase Reference | 501-00-8(CAS DataBase Reference) | | NIST Chemistry Reference | Benzeneacetonitrile, 3-fluoro-(501-00-8) | | EPA Substance Registry System | Benzeneacetonitrile, 3-fluoro- (501-00-8) |
| | 3-Fluorophenylacetonitrile Usage And Synthesis |
| Chemical Properties | clear light yellow to slightly brown liquid | | Uses | 3-Fluorophenylacetonitrile is a phenylacetonitrile derivative that is mainly used in pharmaceutical manufacturing or organic synthesis. It is used as a pharmaceutical intermediate for Lemborexant. The drug is a dual receptor orexin antagonist (DORA) approved for the treatment of primary insomnia. | | Synthesis | General procedure for the synthesis of m-fluorophenylacetonitrile from compound (CAS: 773837-37-9) and 3-fluorobenzyl bromide: Compound 36-1 (1.0 g, 5.3 mmol) and sodium cyanide (520 mg, 10.6 mmol) were dissolved in dimethylsulfoxide (10 mL), and the reaction was stirred at 30 °C overnight. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, the reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (50 mL). The organic phase was washed sequentially with water (10 mL x 5) and saturated sodium bicarbonate solution (20 mL), dried over anhydrous sodium sulfate and concentrated. The residue was purified by fast column chromatography to give product 36-2 as a colorless oil (360 mg, yield: 50%). | | References | [1] Patent: WO2011/11522, 2011, A2. Location in patent: Page/Page column 57
[2] Patent: WO2012/79079, 2012, A1. Location in patent: Page/Page column 63 |
| | 3-Fluorophenylacetonitrile Preparation Products And Raw materials |
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