| Identification | More | [Name]
4-(Trifluoromethoxy)benzonitrile | [CAS]
332-25-2 | [Synonyms]
4-(TRIFLUOROMETHOXY)BENZONITRILE 98
4-(Trifluoromethoxy)benzonitrile 98%
p-trifluoromethoxybenonitrile
4-(Trifluoromethoxy)benzonitrile
p-Cyanotrifluoromethoxybenzene
Benzonitrile, 4-(trifluoromethoxy)-
4-(Trifluoromethyloxy)benzonitrile | [EINECS(EC#)]
206-363-3 | [Molecular Formula]
C8H4F3NO | [MDL Number]
MFCD00039474 | [Molecular Weight]
187.12 | [MOL File]
332-25-2.mol |
| Chemical Properties | Back Directory | [Appearance]
clear light yellow liquid | [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]
332-25-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,T,Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [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 .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
3276 | [WGK Germany ]
3
| [Hazard Note ]
Toxic | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29269090 |
| Hazard Information | Back Directory | [Chemical Properties]
clear light yellow liquid | [Uses]
4-(Trifluoromethoxy)benzonitrile features both cyano and trifluoromethoxy groups as electron-withdrawing substituents, establishing an acceptor–π–acceptor (A–π–A) electronic system[3]. The compound serves as a precursor for fluorophosgene, undergoing quantitative photocatalytic cleavage by an organic photosensitizer to yield benzonitrile and fluorophosgene via single-electron reduction[4]. It is also employed in the synthesis of N-benzyl benzamidine libraries through reaction with variously substituted benzyl amines[5]. | [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 |
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