2,6-Dibromo-4-(trifluoromethoxy)aniline Chemical Properties

Melting point:

70-74 °C(lit.)

Boiling point:

65/0.1mm

Density 

2.036±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

-0.38±0.10(Predicted)

color 

White to Off-White

InChI

InChI=1S/C7H4Br2F3NO/c8-4-1-3(14-7(10,11)12)2-5(9)6(4)13/h1-2H,13H2

InChIKey

JBSWOEGXMADXOU-UHFFFAOYSA-N

SMILES

C1(N)=C(Br)C=C(OC(F)(F)F)C=C1Br

CAS DataBase Reference

88149-49-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-60-37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29222990

MSDS

• Language:English Provider:SigmaAldrich

2,6-Dibromo-4-(trifluoromethoxy)aniline Usage And Synthesis

Uses

2,6-Dibromo-4-(trifluoromethoxy)benzenamine is used in the synthesis of novel pyridylpyrazole acid derivatives in the preparation of agricultural insecticides.

Chemical Properties

Light pink powder

Uses

2,6-Dibromo-4-(trifluoromethoxy)benzenamine is used in the synthesis of novel pyridylpyrazole acid derivatives in the preparation of agricultural insecticides.

Synthesis

The general procedure for the synthesis of 2,6-dibromo-4-(trifluoromethoxy)aniline from p-trifluoromethoxyaniline was as follows: first, 156 g of the crystallized mother liquor containing sodium sulfate was filtered into a 250 mL four-necked flask and the stirring apparatus was started. Subsequently, 17.5 g (0.175 mol) of the reagent was slowly added dropwise, followed by 36.5 g of sodium bromide (0.354 mol) and 30 g (99% purity, 0.168 mol) of 4-trifluoromethoxyaniline. The temperature of the reaction system was adjusted to above 30 °C and the dropwise addition of 38 g of 35% hydrogen peroxide solution was started. During the dropwise addition, if the temperature increased to 50 °C, the reaction temperature was controlled between 50 and 55 °C by adjusting the dropwise acceleration of the coolant. After the dropwise addition was completed, the reaction temperature was maintained to drop and the reaction was continued to be held for 3 hours. Upon completion of the reaction, the system was cooled to about 30°C and the filtration operation was carried out. The resulting filter cake was dried to obtain 55.8 g of white crystals of 2,6-dibromo-4-trifluoromethoxyaniline, which was analyzed by high performance liquid chromatography (HPLC) with a purity of 99.6% and a yield of 99.2%.

References

[1] Patent: CN106631839, 2017, A. Location in patent: Paragraph 0022-0033
[2] Organic Letters, 2011, vol. 13, # 20, p. 5636 - 5639

2,6-Dibromo-4-(trifluoromethoxy)aniline(88149-49-9)Related Product Information

• p-Anisaldehyde
• 4-(Trifluoromethoxy)aniline
• 4'-Methoxyacetophenone
• Aniline
• 2-(Trifluoromethoxy)aniline
• 3-Methoxybenzaldehyde
• 3-(Trifluoromethoxy)aniline
• 4-Methoxybenzoic acid
• 4-(Trifluoromethoxy)benzaldehyde
• 4-(Trifluoromethoxy)chlorobenzene
• (Trifluoromethoxy)benzene
• Anisole
• 4'-(Trifluoromethoxy)acetophenone
• 3-Methoxyacetophenone
• p-Trifluoromethoxy phenol
• 3-(Trifluoromethoxy)bromobenzene
• 2-Bromo-4-trifluoromethoxyaniline
• 3,5-Dibromophenol