4-Amino-3-nitrobenzotrifluoride

4-Amino-3-nitrobenzotrifluoride Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H311Toxic in contact with skin

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P309IF exposed or if you feel unwell:

P310Immediately call a POISON CENTER or doctor/physician.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

4-Amino-3-nitrobenzotrifluoride Chemical Properties,Usage,Production

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