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| | 4-(Trifluoromethoxy)benzonitrile Basic information |
| | 4-(Trifluoromethoxy)benzonitrile Chemical Properties |
| Boiling point | 192-193 °C(lit.) | | density | 1.285 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.452(lit.) | | Fp | 181 °F | | storage temp. | Inert atmosphere,Room Temperature | | form | clear liquid | | color | Colorless to Almost colorless | | BRN | 2832939 | | InChI | InChI=1S/C8H4F3NO/c9-8(10,11)13-7-3-1-6(5-12)2-4-7/h1-4H | | InChIKey | XWHIXOMWXCHJPP-UHFFFAOYSA-N | | SMILES | C(#N)C1=CC=C(OC(F)(F)F)C=C1 | | CAS DataBase Reference | 332-25-2(CAS DataBase Reference) | | EPA Substance Registry System | Benzonitrile, 4-(trifluoromethoxy)- (332-25-2) |
| | 4-(Trifluoromethoxy)benzonitrile Usage And Synthesis |
| Chemical Properties | clear light yellow liquid | | General Description | 4-(Trifluoromethoxy)benzonitrile serves as an intermediate in the synthesis of fluvoxamine. | | Synthesis | To a 25 mL Schlenk tube equipped with a magnetic stirrer were sequentially added CuCl (0.05 mmol, 5 mol%), DABCO (0.10 mmol, 10 mol%) and 4-HO-TEMPO (0.05 mmol, 5 mol%). Subsequently, a solution of acetonitrile (2 mL) with 4-trifluoromethoxybenzyl alcohol (1 mmol) and ammonia (25-28%, 3 mmol, 3.0 equiv) was added. The reaction mixture was stirred at room temperature for 24 h under balloon protection. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate. The organic layers were combined and dried with anhydrous magnesium sulfate. After concentration under reduced pressure, the crude product was purified by column chromatography to give p-trifluoromethoxybenzonitrile. | | References | [1] Advanced Synthesis and Catalysis, 2014, vol. 356, # 18, p. 3892 - 3896
[2] Chinese Chemical Letters, 2018, vol. 29, # 3, p. 464 - 466 |
| | 4-(Trifluoromethoxy)benzonitrile Preparation Products And Raw materials |
| Raw materials | Methanol, 1,1,1-trifluoro-, silver(1+) salt (1:1)-->1-Bromo-4-(trifluoromethoxy)benzene-->4-(TRIFLUOROMETHOXY)BENZALDOXIME-->4-(Trifluoromethoxy)benzyl alcohol-->Copper(I) Cyanide-->Benzenediazonium, 4-cyano-, tetrafluoroborate(1-)-->4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy-->Copper(I) chloride-->Acetonitrile-->Triethylenediamine | | Preparation Products | 4-(Trifluoromethoxy)benzoic acid-->3-METHYL-2-OXAZOLIDONE-->2-Methyl-1[4-(trifluoromethoxy)phenyl] propan-1-one-->3,4-dimethyl-5-phenyl-oxazolidin-2-one-->1-[4-(TRIFLUOROMETHOXY)PHENYL]CYCLOPROPAN-1-AMINE-->4-(TRIFLUOROMETHOXY)THIOBENZAMIDE |
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