ChemicalBook Product Catalog Organic Chemistry Organic fluorine compound Fluorotoluene series 5-Bromo-2-nitrobenzotrifluoride

5-Bromo-2-nitrobenzotrifluoride

Product Name5-Bromo-2-nitrobenzotrifluoride
CAS344-38-7
MFC7H3BrF3NO2
MW270
EINECS670-400-3
MOL File344-38-7.mol

Chemical Properties

Melting point	33-35 °C (lit.)
Boiling point	95-100 °C/5 mmHg (lit.)
Density	1,799 g/cm³
refractive index	1.522-1.524
Flash point	>230 °F
storage temp.	Sealed in dry,Room Temperature
solubility	soluble in Methanol
form	Liquid
color	Clear yellow
BRN	2650701
CAS DataBase Reference	344-38-7(CAS DataBase Reference)

Safety Information

Hazard Codes	Xn,Xi
Risk Statements	36/37/38-20/21/22
Safety Statements	36/37/39-26-37/39-24/25
WGK Germany	3
HazardClass	IRRITANT
HS Code	29049090

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Chemical Properties

clear yellow liquid

Uses

5-Bromo-2-nitrobenzotrifluoride serves as a precursor for synthesizing triphenylamine monomers and diamine intermediates. It undergoes palladium-catalyzed coupling with p-anisidine or bis(4-methoxyphenyl)amine to produce A2B and AB2 type methoxy-protected triphenylamine monomers. Alternatively, Ullmann coupling with activated copper in DMF yields a dinitro biphenyl compound, which is subsequently reduced to the diamine monomer 3,3′-bis(trifluoromethyl)-4,4′-diamino-1,1′-biphenyl[3][4]. The compound is completely reduced to the corresponding aniline in 99% yield using an Fe–phenanthroline/C catalyst and hydrazine hydrate. It has also been examined as a reagent doped into skimmed molecular beams for structural and dynamic studies[1][2].

Synthesis

4-NITRO-3-(TRIFLUOROMETHYL)BENZOIC ACID&

320-38-7

344-38-7

GENERAL PROCEDURE: To a 25 mL round-bottomed flask fitted with a Dimroth condenser (cooled to 10°C) was added 4-nitro-3-(trifluoromethyl)benzoic acid (1.8 mmol), chloroisocyanurate, brominating agent and solvent (8 mL). The mixture was stirred and heated in an oil bath under fluorescent room light (FL) illumination. Upon completion of the reaction, the cooled reaction mixture was filtered through a short silica gel pad, washed with 1 M Na2SO3 aqueous solution, dried over anhydrous Na2SO4, filtered and concentrated in vacuum to give 5-bromo-2-nitrobenzotrifluoride. The resulting product contained 1-5% of the corresponding chlorinated nitro compounds as by-products. The experimental results are detailed in Table 2. Table 2. Results of bromocarboxylation reaction of nitroaromatic carboxylic acids.

References

[1]Jagadeesh, R. V., Wienhöfer, G., Westerhaus, F. A., Surkus, A.-E., Pohl, M.-M., Junge, H., Junge, K., & Beller, M. (2011). Efficient and highly selective iron-catalyzed reduction of nitroarenes. Chemical Communications, 47(39), 10972. https://doi.org/10.1039/c1cc13728j
[2]Bejoy, N. B., & Patwari, G. N. (2023). Photodegradation of Flutamide and Halogen Derivatives of Nitrobenzotrifluoride: The NO Release Channel. The Journal of Physical Chemistry A, 127(34), 7168–7174. https://doi.org/10.1021/acs.jpca.3c03024
[3]Kim, S. D., Byun, T., Lee, B., Kim, S. Y., & Chung, I. S. (2015). Rigid‐Rod Polyamides from 3,3′‐bis(trifluoromethyl)‐4,4′‐diamino‐1,1′‐biphenyl. Macromolecular Chemistry and Physics, 216(12), 1341–1347. https://doi.org/10.1002/macp.201500013
[4]Kang, I., Lee, T., Yoon, Y. R., Kim, J. W., Kim, B.-K., Lee, J., Lee, J. H., & Kim, S. Y. (2021). Synthesis of Arylene Ether-Type Hyperbranched Poly(triphenylamine) for Lithium Battery Cathodes. Materials, 14(24), 7885. https://doi.org/10.3390/ma14247885

References

[1] Patent: WO2017/60906, 2017, A1. Location in patent: Paragraph 00122

Preparation Products And Raw materials

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