ChemicalBook Product Catalog Organic Chemistry Organic fluorine compound Fluorobenzonitrile series 4-(Trifluoromethoxy)benzonitrile

4-(Trifluoromethoxy)benzonitrile

Product Name4-(Trifluoromethoxy)benzonitrile
CAS332-25-2
MFC8H4F3NO
MW187.12
EINECS206-363-3
MOL File332-25-2.mol

Chemical Properties

Boiling point	192-193 °C(lit.)
Density	1.285 g/mL at 25 °C(lit.)
refractive index	n20/D 1.452(lit.)
Flash point	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)

Safety Information

Hazard Codes	Xn,T,Xi
Risk Statements	20/21/22-36/37/38
Safety Statements	26-36/37/39-45
RIDADR	3276
WGK Germany	3
Hazard Note	Toxic
HazardClass	6.1
PackingGroup	III
HS Code	2926909090

MSDS

Provider	Language
4-(Trifluoromethoxy)benzonitrile	English

Usage And Synthesis

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

1736-74-9

332-25-2

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
[3]Zhang, R., Fan, C., Li, J., & Duan, R. (2026). Defective MOF-808 functionalized with electronically tunable deep eutectic solvents as a dual-functional platform for simultaneous flufenacet removal and analysis. Journal of Environmental Management, 415, 130683. https://doi.org/10.1016/j.jenvman.2026.130683
[4]Petzold, D., Nitschke, P., Brandl, F., Scheidler, V., Dick, B., Gschwind, R. M., & König, B. (2018). Visible-Light-Mediated Liberation and In Situ Conversion of Fluorophosgene. Chemistry – A European Journal, 25(1), 361–366. https://doi.org/10.1002/chem.201804603
[5]Beinat, C., Banister, S. D., Hoban, J., Tsanaktsidis, J., Metaxas, A., Windhorst, A. D., & Kassiou, M. (2014). Structure–activity relationships of N-substituted 4-(trifluoromethoxy)benzamidines with affinity for GluN2B-containing NMDA receptors. Bioorganic & Medicinal Chemistry Letters, 24(3), 828–830. https://doi.org/10.1016/j.bmcl.2013.12.087

4-(Trifluoromethoxy)benzonitrile

Chemical Properties

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MSDS

Usage And Synthesis

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