3-BROMO-5-NITROBENZOTRIFLUORIDE Chemical Properties

Boiling point:

223.7±35.0 °C(Predicted)

Density 

1.788±0.06 g/cm3(Predicted)

refractive index 

1.515

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Oil

color 

Colourless

InChI

InChI=1S/C7H3BrF3NO2/c8-5-1-4(7(9,10)11)2-6(3-5)12(13)14/h1-3H

InChIKey

YHTVYRKVFAFVLP-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

630125-49-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38-36/38

Safety Statements 

26-36/37/39-36/37

HazardClass 

IRRITANT

HS Code 

29049090

3-BROMO-5-NITROBENZOTRIFLUORIDE Usage And Synthesis

Description

3-Bromo-5-nitrobenzotrifluoride is an important organic synthetic compound and a pharmaceutical intermediate component. It can be used in the preparation of SOS1 degraders and nilotinib hydrochloride.

Chemical Properties

Yellow liquid

Uses

3-Bromo-5-nitrobenzotrifluoride is an efficient D-glucosamine-based copper catalyst for C-X couplings and its application in synthesis of nilotinib intermediate. 3-Bromo-5-nitrobenzotrifluoride is also an intermediate for Nilotinib (N465300).

Synthesis

Example 14 Synthesis of 1-bromo-3-nitro-5-trifluoromethylbenzene (XI): To a solution of 1-nitro-3-trifluoromethylbenzene (41.1 mL, 300 mmol, 97%, purchased from Aldrich) in dichloromethane (240 mL) was slowly added 98% sulfuric acid (45.7 mL, 840 mmol) over a 10 minute period. The two-phase mixture obtained with vigorous stirring was heated to 35 °C and 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (total 53.1 g, 180 mmol) was added in six equal portions over 5 hours. The mixture was continued to be stirred at 35 °C for 19 h. HPLC analysis showed more than 97% conversion of the starting material. After the reaction mixture was cooled to room temperature, it was added dropwise to a stirred aqueous 2 M NaOH solution (210 mL) at 0-5 °C over 20 min, during which time it was cooled in an ice-water bath, and the internal temperature was briefly raised to about 35 °C. The reaction mixture was then cooled to room temperature, and the internal temperature was raised to about 35 °C. The reaction mixture was then cooled to room temperature. The two layers were separated and the aqueous layer was extracted with hexane (3 x 200 mL). The combined organic layers were washed sequentially with water (200 mL), 5% aqueous sodium bisulfite (2 x 200 mL), 8% aqueous NaHCO3 (200 mL), and 10% aqueous NaCl (200 mL), followed by evaporation of the solvent at 45 °C under reduced pressure. The resulting liquid was distilled at 0.71 mbar and a bath temperature of 70-80 °C to give 1-bromo-3-nitro-5-trifluoromethylbenzene as a light yellow liquid in 89.6% yield (1H-NMR purity about 95%).1H-NMR (400 MHz, CDCl3): δ 8.11 (m, 1H), 8.45 (m, 1H), 8.58-8.59 (m, 1H). 1H). Boiling point: ca. 68 °C (0.71 mbar).

References

[1] Patent: WO2006/135640, 2006, A2. Location in patent: Page/Page column 25-26
[2] RSC Advances, 2015, vol. 5, # 2, p. 1522 - 1528
[3] Patent: US2016/311777, 2016, A1. Location in patent: Paragraph 0028

3-BROMO-5-NITROBENZOTRIFLUORIDE(630125-49-4)Related Product Information

• 2-BROMO-3-FLUORO-4-PICOLINE
• 3-Bromo-5-(trifluoromethyl)pyridine
• 3-BROMO-5-FLUORO-2-METHOXYPYRIDINE
• 3-BROMO-2-FLUORO-4-IODOPYRIDINE
• 3-BROMO-5-NITROBENZOTRIFLUORIDE
• 4-AMINO-3-BROMO-5-NITROBENZOTRIFLUORIDE
• 2-Bromo-5-nitrobenzotrifluoride98%,2-BROMO-5-NITROBENZOTRIFLUORIDE
• 3-Bromo-4-nitrobenzotrifluoride
• 5-Bromo-2-nitrobenzotrifluoride 98%,5-Bromo-2-nitrobenzotrifluoride98%,5-BROMO-2-NITROBENZOTRIFLUORIDE,5-Bromo-2-nitrobenzotrifluoride, 97+%
• 4-Bromo-3-nitrobenzotrifluoride
• 2-Amino-5-Bromo-3-Nitrobenzotrifluoride
• 2-BROMO-6-NITRO-4-TRIFLUOROMETHYLTOLUENE
• 2-BROMO-4-TRIFLUOROMETHYL-6-NITROPHENYLISOTHIO-CYANATE
• 4-Bromo-2-nitrobenzotrifluoride
• 2-BROMO-3-NITROBENZOTRIFLUORIDE
• 3-Bromo-2-nitrobenzotrifluoride
• BUTTPARK 62\11-04
• 2-BROMO-6-NITRO-4-(TRIFLUOROMETHYL)PHENYL 4-CHLORO-3-NITROBENZOATE