4-(Trifluoromethoxy)aniline Chemical Properties

Boiling point:

73-75 °C10 mm Hg(lit.)

Density 

1.32 g/mL at 20 °C(lit.)

refractive index 

n20/D 1.463(lit.)

Flash point:

177 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

pka

3.75±0.10(Predicted)

form 

Liquid

color 

Clear colorless to yellow

Specific Gravity

1.310

BRN 

2090209

Stability:

Hygroscopic

InChI

InChI=1S/C7H6F3NO/c8-7(9,10)12-6-3-1-5(11)2-4-6/h1-4H,11H2

InChIKey

XUJFOSLZQITUOI-UHFFFAOYSA-N

SMILES

C1(N)=CC=C(OC(F)(F)F)C=C1

CAS DataBase Reference

461-82-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xi,Xn

Risk Statements 

24/25-33-38-41-36/37/38-20/21/22

Safety Statements 

26-36/37/39-45-36

RIDADR 

UN 2941 6.1/PG 3

WGK Germany 

2

Hazard Note 

Toxic

HazardClass 

IRRITANT, TOXIC

HazardClass 

6.1

PackingGroup 

III

HS Code 

29222900

MSDS

• Language:English Provider:4-(Trifluoromethoxy)aniline
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-(Trifluoromethoxy)aniline Usage And Synthesis

Chemical Properties

CLEAR YELLOW LIQUID

Uses

4-(Trifluoromethoxy)aniline was used in the synthesis of:

• side-group liquid-crystalline polymethacrylates with fluorine-containing mesogens
• derivatives of 3-(quinolin-3-yl)acrylates
• series of novel Shiff bases, via condensation with pyridinecarboxaldehydes in the presence of molecular sieves

Uses

4-(Trifluoromethoxy)aniline is used in the synthesis of anticancer agents and antitumor medicaments. Also, its an intermediate in the production of labelled Riluzole, a neuroprotective agent. Modulates glutamatergic transmission. A glutamate release inhibitor. An anticonvulsant.

Synthesis

General procedure: To a flame-dried 25 mL round-bottom flask were added activated magnesium chips (7.5 mmol, 1.5 eq.) and 5 mL of anhydrous tetrahydrofuran (THF). Two drops of 1,2-dibromoethane were added to the suspension to initiate the reaction. 5 min later, a solution of p-bromotrifluoromethoxybenzene (5 mmol, 1.0 eq.) dissolved in 5 mL of anhydrous THF was slowly added to the magnesium suspension at room temperature. A mild exothermic phenomenon was observed during the reaction. After determining the concentration of Grignard's reagent by titration, 1 mmol of the reagent was transferred to another flame-dried reaction flask. The solution was diluted with 3 mL of anhydrous toluene and after cooling to the preset temperature T, a solution of oxazepane (1.2 mmol, 1.2 equiv) dissolved in 1 mL of anhydrous toluene was added. The reaction mixture was held at temperature T for a reaction time t, followed by quenching the reaction with saturated aqueous ammonium chloride (NH4Cl). (Specific reaction temperatures and reaction times need to be listed according to the actual conditions of each substrate.)

References

[1] Organic Letters, 2013, vol. 15, # 14, p. 3734 - 3737
[2] Nature Chemistry, 2017, vol. 9, # 7, p. 681 - 688
[3] Patent: US2018/57444, 2018, A1. Location in patent: Paragraph 0098; 0134; 0135; 0171

4-(Trifluoromethoxy)aniline(461-82-5)Related Product Information

• 4-Methoxyphenylacetone
• 4'-(Trifluoromethoxy)acetophenone
• o-Anisaldehyde
• Anisole
• (Trifluoromethoxy)benzene
• 3-Methoxybenzaldehyde
• 4-(Trifluoromethoxy)chlorobenzene
• 2-(Trifluoromethoxy)aniline
• 4-Aminobenzotrifluoride
• (3-Methoxyphenyl)acetonitrile
• 4-Methoxyphenylacetic acid
• 4-Methoxybenzylchloride
• p-Trifluoromethoxy phenol
• 3-(Trifluoromethoxy)aniline
• Trimethyl phosphite
• 2-Fluoroaniline
• Aniline
• 4-Fluoroaniline