4-Amino-3-nitrobenzotrifluoride Chemical Properties

Melting point:

105-106 °C(lit.)

Boiling point:

265.6±40.0 °C(Predicted)

Density 

1.4711 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol,Toluene

pka

-2.54±0.10(Predicted)

form 

Crystals or Crystalline Powder

color 

Yellow to golden

BRN 

650808

InChI

InChI=1S/C7H5F3N2O2/c8-7(9,10)4-1-2-5(11)6(3-4)12(13)14/h1-3H,11H2

InChIKey

ATXBGHLILIABGX-UHFFFAOYSA-N

SMILES

C1(N)=CC=C(C(F)(F)F)C=C1[N+]([O-])=O

CAS DataBase Reference

400-98-6(CAS DataBase Reference)

NIST Chemistry Reference

Aniline, 2-nitro-4-trifluoromethyl-(400-98-6)

EPA Substance Registry System

Benzenamine, 2-nitro-4-(trifluoromethyl)- (400-98-6)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37

RIDADR 

UN2811

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29214300

MSDS

• Language:English Provider:2-Nitro-4-(trifluoromethyl)aniline
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Amino-3-nitrobenzotrifluoride Usage And Synthesis

Chemical Properties

White to yellow crystal powder

Uses

4-Amino-3-nitrobenzotrifluoride can be used as pharmaceutical and pesticide intermediates.

Synthesis

N-(2-nitro-4-(trifluoromethyl)phenyl)acetamide (109.5 g, 0.5 mol) was used as a raw material and was mixed with 94% sulfuric acid solution (171.5 g) at a stirring rate of 550 rpm, and the reaction temperature was controlled to be 28 °C. Subsequently, 98% nitric acid solution (32.5 g, 0.51 mol) was added dropwise to the mixture at a dropwise acceleration rate of 40 g/min. After the dropwise addition, the nitrification reaction was continued for 2 hours. After completion of the reaction, the reaction system was heated to 80°C and the deacetylation reaction was carried out for 5 hours to obtain the deacetylated product. The deacetylation product was cooled to below 45°C and slowly added to ice water to precipitate the solid. The resulting solid was filtered and washed, followed by alkaline washing with 10% aqueous sodium hydroxide solution until the pH of the filtrate reached 7, terminating the alkaline washing process. The alkali washed solid was dried at 55 °C for 4.5 h. 104 g of 4-trifluoromethoxy-2-nitroaniline was finally obtained, which was analyzed by GC with a purity of 98.5% and a yield of 94%.

References

[1] Kogyo Kagaku Zasshi, 1959, vol. 62, p. 706,708
[2] Chem. Zentralbl., 1960, vol. 131, p. 7854
[3] Journal of Medicinal Chemistry, 1995, vol. 38, # 10, p. 1786 - 1792
[4] Organic and Biomolecular Chemistry, 2016, vol. 14, # 9, p. 2645 - 2650
[5] Patent: CN107032965, 2017, A. Location in patent: Paragraph 0081; 0084; 0085; 0095; 0099; 0100; 0111; 0112

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