445-02-3

Basic information

• Product Name: 2-Amino-5-bromobenzotrifluoride
• Synonyms: 4-BROMO-2-(TRIFLUOROMETHYL)ANILINE;4-Bromo-alpha,alpha,alpha-trifluoro-o-toluidine;2-AMINO-5-BROMO(TRIFLUOROMETHYL)BENZENE;2-AMINO-5-BROMOBENZOTRIFLUORIDE;4-bromo-2-(trifluoromethyl)-benzenamin;o-Toluidine, 4-bromo-alpha,alpha,alpha-trifluoro-;2-Amino-5-bromobenzotrifluoride, 98% (4-Bromo-2-trifluoromethylaniline);2-Amino-5-bromobenzotrifluoride 98%
• CAS NO: 445-02-3
• Molecular Formula: C₇H₅BrF₃N
• Molecular Weight: 240.02
• EINECS: 207-150-8
• Product Categories: Trifluoromethylbenzene serise;Aromatic Halides (substituted);Aniline;Benzotrifluoride Series;Amines;C7;Nitrogen Compounds
• Mol File: 445-02-3.mol

Chemical Properties

• Melting Point: 33-34℃
• Boiling Point: 84-86 °C5 mm Hg(lit.)
• Flash Point: 225 °F
• Appearance: Clear yellow liquid
• Density: 1.71 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0955mmHg at 25°C
• Refractive Index: n20/D 1.532(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 0.76±0.10(Predicted)
• BRN: 2211504
• CAS DataBase Reference: 2-Amino-5-bromobenzotrifluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-bromobenzotrifluoride(445-02-3)
• EPA Substance Registry System: 2-Amino-5-bromobenzotrifluoride(445-02-3)

Safety Data

• Hazard Codes: Xn,Xi,C
• Statements: 20/21/22-36/37/38-34
• Safety Statements: 26-36-36/37/39-45-27
• WGK Germany: 3
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 445-02-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-5-bromobenzotrifluoride is used as a reagent for the synthesis of α-aminophosphonate, a compound that exhibits moderate antitumor activity. Its role in the creation of such bioactive molecules makes it a valuable component in the development of potential cancer-fighting drugs.
Used in Chemical Synthesis:
In the chemical synthesis industry, 2-Amino-5-bromobenzotrifluoride is used as a key intermediate in the preparation of various benzene derivatives. These derivatives are essential in the production of a wide range of chemical products, including pharmaceuticals, agrochemicals, and other specialty chemicals.
The provided materials highlight the importance of 2-Amino-5-bromobenzotrifluoride in both the pharmaceutical and chemical synthesis industries. Its versatility as a reagent and its role in the synthesis of compounds with potential antitumor activity make it a valuable asset in the development of new and innovative products.

InChI:InChI=1/C7H5BrF3N/c8-4-1-2-6(12)5(3-4)7(9,10)11/h1-3H,12H2

Upstream product

• 344-38-7 4-bromo-1-nitro-2-(trifluoromethyl)benzene 
• 88-17-5 2-(trifluoromethyl)benzenamine 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 98-08-8 α,α,α-trifluorotoluene 
• 98-16-8 3-trifluoromethylaniline 
• 887144-94-7 Togni's reagent II 
• 106-40-1 4-bromo-aniline 
• 2926-29-6 Langlois reagent 
• 75-63-8 Bromotrifluoromethane 
• 2314-97-8 iodotrifluoromethane 
• 14547-73-0 N-(4-bromophenyl)picolinamide 

Downstream Products

• 364-12-5 4-bromo-1-iodo-2-(trifluoromethyl)benzene 
• 92524-80-6 N-(4-Bromo-2-trifluoromethyl-phenyl)-5-(4-chloro-benzoyl)-2-hydroxy-3-methyl-benzamide 
• 765948-84-3 4-[4-amino-3-(trifluoromethyl)phenyl]-1-isoindolinone 
• 320-31-0 4-bromo-2-(trifluoromethyl)benzoic acid 
• 157026-19-2 5-bromo-3-(trifluoromethyl)-1,2-benzenediamine 
• 157026-18-1 4-bromo-2-nitro-6-trilfuoromethyl-phenylamine 
• 179062-00-1 N-(4-bromo-2-nitro-6-trifluoromethyl-phenyl)-acetamide 
• 300356-31-4 (4-bromo-2-(trifluoromethyl)phenyl)(methyl)sulfane 
• 29124-62-7 N-(4-bromo-2-trifluoromethyl-phenyl)-acetamide 
• 666263-15-6 2-(2-trifluoromethyl-4-bromo-phenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid (tetrahydro-pyran-4-ylmethyl)-amide 
• 262433-04-5 N₁-[4-bromo-2-(trifluoromethyl)phenyl]-1-benzenesulfonamide 
• 312303-71-2 4-bromo-2-trifluoromethyl-phenylhydrazine 

Relevant articles and documents

Method for synthesizing 3 -chloro -5 -trifluoromethyltrifluoroacetophenone

The invention discloses a method for synthesizing 3 -chloro -5 -trifluoromethyltrifluoroacetophenone, which comprises the following steps: firstly bromination and rechlorination of o-aminotrifluorotoluene to obtain 4 - bromo -2 - chloro -6 - trifluoromethylaniline. 4 - Bromo -2 - chloro -6 - trifluoromethylaniline was subjected to diazotization followed by treatment with hypophosphorous acid or ethanol to give the deamination compound 1 - bromo -3 - chloro -5 - (trifluoromethyl) benzene. 1 - Bromo -3 - chloro -5 - (trifluoromethyl) benzene was made into Grignard reagent with magnesium chips and reacted with the acylating agent to give 3 - chloro -5 - trifluoromethyltrifluoroacetophenone. The starting material ortho-aminotrifluorotoluene used in the route is a common chemical with cheap price, and the obtained product is high in purity and yield, relatively small in environmental pollution and expected to be used for large-scale industrial production.

Transition metal-free direct C–H trifluoromethyltion of (hetero)arenes with Togni's reagent

A new transition-metal-free direct C–H trifluoromethylation reaction of (hetero)arenes with Togni's reagent was developed. This transformation proceeded smoothly under mild conditions and exhibited good tolerance of many synthetically relevant functional groups. It provided an alternative approach for the synthesis of trifluoromethylated (hetero)arenes.

Preparation method of trifluoromethylated aniline compound

The invention provides a preparation method of a trifluoromethylated aniline compound shown in a formula (IIA) or a formula (IIB). The method comprises the following steps: by taking a mixed solvent of DMF and water in a volume ratio of 1:(1-4) as a reaction medium, adding an aniline compound shown in a formula (IA) or a formula (IB), 1-(trifluoromethyl)-1,2-benziodoxol-3-(1H)-one and a photocatalyst, and reacting for 2-6 hours at room temperature under blue light; and carrying out post-treatment on the obtained reaction mixture to obtain the trifluoromethylated aniline compound as shown in the formula (IIA) or the formula (IIB). According to the method, by the photocatalyst, the reaction is driven to be carried out under the irradiation of visible light, the reaction conditions are mild,the site selectivity is high, the reaction is efficient, green and environment-friendly, the reaction yield can reach 90%, and the product can be prepared by only one step.

Delayed fluorescence from a zirconium(iv) photosensitizer with ligand-to-metal charge-transfer excited states

Advances in chemical control of the photophysical properties of transition-metal complexes are revolutionizing a wide range of technologies, particularly photocatalysis and light-emitting diodes, but they rely heavily on molecules containing precious metals such as ruthenium and iridium. Although the application of earth-abundant ‘early’ transition metals in photosensitizers is clearly advantageous, a detailed understanding of excited states with ligand-to-metal charge transfer (LMCT) character is paramount to account for their distinct electron configurations. Here we report an air- and moisture-stable, visible light-absorbing Zr(iv) photosensitizer, Zr(MesPDPPh)2, where [MesPDPPh]2? is the doubly deprotonated form of [2,6-bis(5-(2,4,6-trimethylphenyl)-3-phenyl-1H-pyrrol-2-yl)pyridine]. This molecule has an exceptionally long-lived triplet LMCT excited state (τ = 350 μs), featuring highly efficient photoluminescence emission (Ф = 0.45) due to thermally activated delayed fluorescence emanating from the higher-lying singlet configuration with significant LMCT contributions. Zr(MesPDPPh)2 engages in numerous photoredox catalytic processes and triplet energy transfer. Our investigation provides a blueprint for future photosensitizer development featuring early transition metals and excited states with significant LMCT contributions. [Figure not available: see fulltext.]

Utilization of a Hydrogen Source from Renewable Lignocellulosic Biomass for Hydrogenation of Nitroarenes

Exploring of hydrogen source from renewable biomass, such as glucose in alkaline solution, for hydrogenation reactions had been studied since 1860s. According to proposed pathway, only small part of hydrogen source in glucose was utilized. Herein, the utilization of a hydrogen source from renewable lignocellulosic biomass, one of the most abundant renewable sources in nature, for a hydrogenation reaction is described. The hydrogenation is demonstrated by reduction of nitroarenes to arylamines in up to 95 % yields. Mechanism studies suggest that the hydrogenation occurs via a hydrogen transformation pathway.

Nickel-Catalyzed Direct C-H Trifluoromethylation of Free Anilines with Togni's Reagent

An efficient nickel-catalyzed C-H trifluoromethylation for the synthesis of trifluoromethylated free anilines using Togni's reagent has been developed. This approach exhibits a good functional group tolerance, good regioselectivity, and chemoselectivity under mild conditions. The newly developed economical one-step method is a better alternative to synthesize trifluoromethylated free anilines.

Preparation method of trifluoromethylamine

The invention relates to a preparation method of trifluoromethylamine. The method includes the following steps that aromatic amine shown in the formula (1) and a trifluoromethyl reagent shown in the formula (2) react in a solvent under the condition that an alkali and/or nickel compound exists, and the trifluoromethylamine compound shown in the formula (3) is generated. According to the preparation method of trifluoromethylamine, aromatic amine and 1-trifluoromethyl-1,2-iodobenzoyl-3(H)-ketone serve as raw materials and react under the condition that the alkali and/or nickel compound exists through the amino positioning effect on aromatic nucleus. The synthesis steps of the method are simple, the cost of the raw materials is low, the production cost of trifluoromethylamine can be greatly reduced, and large-scale industrialized production is promoted.

Coordinating Activation Strategy-Induced Selective C?H Trifluoromethylation of Anilines

A simple protocol for the synthesis of 2-(trifluoromethyl)aniline derivatives through a coordinating activation strategy was developed. The reaction showed good reactivity and gave the target products in moderate to good yields. Pleasingly, the directing group could be recovered in excellent yield. Furthermore, this strategy allowed efficient access to the synthesis of floctafenine. A single-electron-transfer mechanism was proposed to be responsible for this trifluoromethylation reaction.

Synthetic method of aminobenzotrifluoride and derivant thereof

The invention discloses a synthetic method of aminobenzotrifluoride and a derivant thereof. By adopting a method for performing amino-ortho-position trifluoromethylation on an amino-benzene compound,trifluoromethyl trimethylsilane is used a reaction reagent, free radical substitution reaction is carried out on an amino-ortho-position of the amino-benzene compound and then trifluoromethylation isdirectly carried out, so that a target product is obtained. The method disclosed by the invention has the advantages that raw materials are cheap and easy to obtain, the production is convenient, precious metal is not needed, environmental protection and safety are achieved, and purification is easy to carry out; the method can be developed into an industrial production method. Based on that, according to the synthetic method disclosed by the invention, screening and optimization on synthetic conditions of the compound are also carried out, so that the reaction yield is further improved.

Chemoselective Hydrogenation of Nitroarenes Catalyzed by Molybdenum Sulphide Clusters

Herein, we describe an atom efficient and general protocol for the chemoselective hydrogenation of nitroarenes to anilines catalyzed by well-defined diimino and diamino cubane-type Mo3S4 clusters. The novel diimino [Mo3S4Cl3(dnbpy)3]+ ([5]+) (dnbpy=4,4′-dinonyl-2,2′-dipyridyl, L1) trinuclear complex was synthesized in high yields by simple ligand substitution reactions starting from the thiourea (tu) [Mo3S4(tu)8(H2O)]Cl4?4 H2O (3) precursor. This strategy has also been successfully adapted for the isolation of the diamino [Mo3S4Cl3(dmen)3](BF4) ([6](BF4)), (dmen=N,N′-dimethylethylenediamine) salt. Applying these catalysts, high selectivity in the hydrogenation of functionalized nitroarenes has been accomplished. Over thirty anilines bearing synthetically functional groups have been synthesized in 70 to 99 % yield. Notably, the integrity of the cluster core is preserved during catalysis. Based on kinetic studies on the hydrogenation of nitrobenzene and other potential reaction intermediates, the direct reduction to aniline is the preferential route.