630125-49-4

Basic information

• Product Name: 3-BROMO-5-NITROBENZOTRIFLUORIDE
• Synonyms: 1-BROMO-3-NITRO-5-(TRIFLUOROMETHYL)BENZENE;3-BROMO-5-NITROBENZOTRIFLUORIDE;3-Bromo-5-nitrobenzotrifluoride 97%;3-Bromo-5-nitrobenzotrifluoride97%;BENZENE,1-BROMO-3-NITRO-5;5-bromo-3-nitrobenzotrifluoride;5-Bromo-3-(Trifluoromethyl)nitrobenzene;Benzene,1-broMo-3-nitro-5-(trifluoroMethyl)-
• CAS NO: 630125-49-4
• Molecular Formula: C₇H₃BrF₃NO₂
• Molecular Weight: 270
• Product Categories: Fluorine series
• Mol File: 630125-49-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 223.7 °C at 760 mmHg
• Flash Point: 89.1 °C
• Appearance: /
• Density: 1.788 g/cm³
• Refractive Index: 1.515
• Storage Temp.: Room temperature.
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 3-BROMO-5-NITROBENZOTRIFLUORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-5-NITROBENZOTRIFLUORIDE(630125-49-4)
• EPA Substance Registry System: 3-BROMO-5-NITROBENZOTRIFLUORIDE(630125-49-4)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38-36/38
• Safety Statements: 26-36/37/39-36/37
• HazardClass: IRRITANT
• Hazardous Substances Data: 630125-49-4(Hazardous Substances Data)

Usage

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).

Upstream product

• 479411-92-2 2-(3-bromo-5-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 320-94-5 2-nitro-4-trifluoromethylbenzoic acid 
• 98-08-8 α,α,α-trifluorotoluene 
• 98-46-4 3-trifluoromethylnitrobenzene 

Downstream Products

• 54962-75-3 [3-bromo-5-(trifluoromethyl)phenyl]amine 
• 96100-12-8 3-methyl-5-(trifluoromethyl)aniline 
• 96783-80-1 1-Methyl-3-nitro-5-trifluoromethyl-benzene 
• 1227582-49-1 3-nitro-5-(trifluoromethyl)benzene-1-sulfonyl chloride 

Relevant articles and documents

meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation

Herein, we report the meta-nitration of arenes bearing ortho/para directing group(s) using the iridium-catalyzed C?H borylation reaction followed by a newly developed copper(II)-catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes in a one-pot fashion. This protocol allows the synthesis of meta-nitrated arenes that are tedious to prepare or require multistep synthesis using the existing methods. The reaction tolerates a wide array of ortho/para-directing groups, such as ?F, ?Cl, ?Br, ?CH3, ?Et, ?iPr ?OCH3, and ?OCF3. It also provides regioselective access to the nitro derivatives of π-electron-deficient heterocycles, such as pyridine and quinoline derivatives. The application of this method is demonstrated in the late-stage modification of complex molecules and also in the gram-scale preparation of an intermediate en route to the FDA-approved drug Nilotinib. Finally, we have shown that the nitro product obtained by this strategy can also be directly converted to the aniline or hindered amine through Baran's amination protocol.

Method for preparing nilotinib intermediate

Disclosed in the present invention is a method for preparing nilotinib intermediate 3-(4-methyl-1H-imidazol-1-yl)-5trifluoromethyl phenylamine (I). The method comprises the following steps: taking trifluorotoluene as an initial material, and preparing the nilotinib intermediate (I) by nitration, bromization, condensation and reduction successively Compared with the prior art, the preparation method has the following advantages: a relatively high yield, the raw materials are easily obtained, a concise process and few side reactions, and is adapted to industrial production, so the development of an economic technology of the bulk drug is pro moted.

PROCESS FOR THE SYNTHESIS OF ORGANIC COMPOUNDS

The present invention provides an efficient, safe and cost effective way to prepare 5 (4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzenamine which is a key intermediate for the preparation of substituted pyrimidinylaminobenzamides of formula (II).