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Cas Database

1003-99-2

1003-99-2

Identification

  • Product Name:2-Bromo-5-fluoroaniline

  • CAS Number: 1003-99-2

  • EINECS:

  • Molecular Weight:190.015

  • Molecular Formula: C6H5BrFN

  • HS Code:29214200

  • Mol File:1003-99-2.mol

Synonyms:2-Bromo-5-fluoro-phenylamine;2-bromo-5-fluoro-aniline;2-Bromo-fluoroaniline;2-bromo-5-fluorobenzenamine;2-fluoro-5-bromoaniline;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi,ToxicT

  • Hazard Codes:Xi,T

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:2-Bromo-5-fluoroaniline
  • Packaging:1g
  • Price:$ 45
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Bromo-5-fluoroaniline >98.0%(GC)
  • Packaging:5g
  • Price:$ 59
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Bromo-5-fluoroaniline >98.0%(GC)
  • Packaging:25g
  • Price:$ 177
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2-Bromo-5-fluoroaniline 98%
  • Packaging:100 g
  • Price:$ 76
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2-Bromo-5-fluoroaniline 98%
  • Packaging:25 g
  • Price:$ 32
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2-Bromo-5-fluoroaniline 97%
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  • Price:$ 35
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:2-Bromo-5-fluoroaniline 98%
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  • Price:$ 15
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:2-Bromo-5-fluoroaniline 98%
  • Packaging:500g
  • Price:$ 191
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  • Manufacture/Brand:Frontier Specialty Chemicals
  • Product Description:2-Bromo-5-fluoroaniline 98%
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  • Manufacture/Brand:Frontier Specialty Chemicals
  • Product Description:2-Bromo-5-fluoroaniline 98%
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Relevant articles and documentsAll total 15 Articles be found

Palladium-catalyzed reaction of aryl iodides with ortho-bromoanilines and norbornene/norbornadiene: Unexpected formation of dibenzoazepine derivatives

Della Ca', Nicola,Maestri, Giovanni,Malacria, Max,Derat, Etienne,Catellani, Marta

, p. 12257 - 12261 (2011)

Expecting the unexpected: The title reaction leads to satisfactory yields of dihydrodibenzoazepines 1-a from norbornene. The dibenzoazepines 2 can also be accessed from compounds of type 1-b when norbornadiene is used as a reactant. Theoretical studies show that the reaction represents a chelation-driven deviation from the usual selectivity observed in the presence of ortho-substituents on the aryl iodide.

Highly selective hydrogenation of halogenated nitroarenes over Ru/CN nanocomposites by: In situ pyrolysis

Yue, Shengnan,Wang, Xueguang,Li, Shaoting,Sheng, Yao,Zou, Xiujing,Lu, Xionggang,Zhang, Chunlei

, p. 11861 - 11869 (2020)

A highly chemoselective and recyclable ruthenium catalyst for the hydrogenation of halogenated nitroarenes has been prepared via the simple in situ calcination of a mixture of melamine, glucose and ruthenium trichloride. Superfine Ru particles (2.3 ± 0.3 nm) were obtained and highly dispersed in the nitrogen-doped carbon matrix. The Ru/CN catalyst smoothly transforms a variety of halogenated nitroarenes to the corresponding haloanilines with high intrinsic activity (e.g. TOF = 1333 h-1 for p-chloronitrobenzene) and selectivity of more than 99.6percent. Furthermore, through an analysis of the products in the reaction process, it was concluded that there are two parallel reaction pathways (a direct pathway and an indirect pathway) for the hydrogenation of aromatic nitro compounds over the Ru/CN catalyst, and the direct pathway was proved to be dominant in catalyzing the intermediates. This journal is

Electrophilic bromination of meta-substituted anilines with N-bromosuccinimide: Regioselectivity and solvent effect

Bartoli, Sandra,Cipollone, Amalia,Squarcia, Antonella,Madami, Andrea,Fattori, Daniela

, p. 1305 - 1308 (2009)

N-Bromosuccinimide-mediated electrophilic aromatic bromination of a series of anilines substituted with an electron-with-drawing group in the meta position was investigated. The regioselectivity of the reaction is markedly dependent on the polarity of the solvent and the bromination reaction can be tuned by appropriate selection of the reaction medium. Georg Thieme Verlag Stuttgart.

Preparation of Well-Ordered Mesoporous-Silica-Supported Ruthenium Nanoparticles for Highly Selective Reduction of Functionalized Nitroarenes through Transfer Hydrogenation

Wei, Ning,Zou, Xiujing,Huang, Haigen,Wang, Xueguang,Ding, Weizhong,Lu, Xionggang

, p. 209 - 214 (2018)

MCM-41-type mesoporous silica (OMS-IL) was prepared by using an ionic liquid (1-hexadecyl-3-methylimidazolium bromide) as a template. The XRD and TEM results demonstrated that OMS-IL was more stable than the MCM-41 material. Ru nanoparticles were supported on OMS-IL (Ru/OMS-IL) by impregnating OMS-IL with a RuCl3 aqueous solution, and the resulting material was used for the selective reduction of nitroarenes. The effects of the components of the catalysts and the reaction conditions on the catalytic behavior of the prepared catalysts were investigated in detail. Ru/OMS-IL exhibited high catalytic activity and chemoselectivity for the reduction of various substituted nitroarenes to the corresponding aromatic amines in ethanol with hydrazine hydrate as a hydrogen donor under mild conditions. The Ru/OMS-IL catalysts were highly stable and could easily be recovered by simple filtration over at least six recycling reactions without any observable loss in catalytic performance.

N-doped graphitic carbon-improved Co-MoO3 catalysts on ordered mesoporous SBA-15 for chemoselective reduction of nitroarenes

Huang, Haigen,Liang, Xiangcheng,Wang, Xueguang,Sheng, Yao,Chen, Chenju,Zou, Xiujing,Lu, Xionggang

, p. 127 - 137 (2018)

Metallic Co-MoO3 catalysts supported on ordered mesoporous SBA-15 were first prepared through in situ reaction of SBA-15-supported Co-Mo oxides with 1,10-phenanthroline. The resulting Co-MoO3/NC@SBA-15 catalysts with N-doped carbon (NC) exhibited high catalytic activity and chemoselectivity for selective reduction of various functionalized nitroarenes to the corresponding arylamines in ethanol with hydrazine hydrate at near room temperature (30 °C). For reduction of all tested substrates (28 examples), the catalyst could afford a conversion of >99% and arylamine selectivity of >99%. The excellent catalytic performance of the Co-MoO3/NC@SBA-15 was attributed to the Co-Nχ(C)-Mo active sites generated through the interaction between the surface Co-Nχ(C) and MoO3 species, promoting the dissociation of hydrazine molecule into the active H* species for the reduction of nitro groups. After the seventh cycle for reduction of 4-methoxylnitrobenzene, the 2%Co-MoO3/NC@SBA-15 showed little change in catalytic performance, textural properties, size and dispersion of metal species and valence states of elements, indicating high stability and recyclability.

Efficient and recyclable bimetallic Co–Cu catalysts for selective hydrogenation of halogenated nitroarenes

Lu, Xionggang,Ren, Jiaan,Sheng, Yao,Wang, Xueguang,Wu, Baoqin,Zou, Xiujing

, (2021/12/20)

Silica supported N-doped carbon layers encapsulating Co–Cu nanoparticles (Co1Cux@CN/SiO2) were prepared by a one-step impregnation of Co(NO3)2·6H2O, Cu(NO3)2·3H2O, urea and glucose, following in situ carbothermal reduction. Effects of Cu contents on the catalytic performance of the Co1Cux@CN/SiO2 catalysts were investigated for selective hydrogenation of p-chloronitrobenzene to p-chloroaniline. The Co1Cu0.30@CN/SiO2 with Cu/Co molar ratio of 0.30:1 presented much higher activity and stability than the monometallic Co@CN/SiO2 catalyst. The addition of Cu into Co1Cux@CN/SiO2 catalysts had favorable effects on the formation of highly active Co–N sites and N-doped carbon layer. The role of the N-doped carbon layer was to protect the Co from oxidation by air, and the Co1Cu0.30@CN/SiO2 could be reused for at least 12 cycles without decrease in catalytic efficiency. Mechanistic and in situ infrared studies revealed that the interaction effect between the Co and Cu atoms made the surface of Co highly electron rich, which decreased adsorption of halogen groups and resulting in the enhanced selectivity during chemoselective hydrogenation of halogenated nitroarenes for a wide scope of substrates.

Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications

Zhao, Lixing,Hu, Chenyang,Cong, Xuefeng,Deng, Gongda,Liu, Liu Leo,Luo, Meiming,Zeng, Xiaoming

supporting information, p. 1618 - 1629 (2021/01/25)

Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 × 106). Mechanistic studies, based on theoretical calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several commercially available pharmaceuticals by means of this strategy highlights its potential application in medicinal chemistry.

Method for preparing 2-bromo-5-fluoroaniline

-

, (2020/12/31)

The invention discloses a method for preparing 2-bromo-5-fluoroaniline, belonging to the field of organic chemical synthesis. The preparation method comprises the following steps: with 4-fluoroanilineas a raw material, reacting 4-fluoroaniline with acetic anhydride to generate 4-fluoroacetanilide; performing nitrification; replacing acetamido groups with bromine; and reducing nitro groups. Thus,the 2-bromo-5-fluoroaniline with high yield and high purity is prepared. The method has the advantages of high product yield, high purity, easy availability of raw materials and simple operation, andis beneficial to industrial production.

In Situ Synthesized Silica-Supported Co@N-Doped Carbon as Highly Efficient and Reusable Catalysts for Selective Reduction of Halogenated Nitroaromatics

Sheng, Yao,Wang, Xueguang,Yue, Shengnan,Cheng, Gonglin,Zou, Xiujing,Lu, Xionggang

, p. 4632 - 4641 (2020/07/30)

Silica-supported Co@N-doped carbon (Co@CN/SiO2) catalysts were first prepared by a one-step impregnation with a mixed solution of cobalt nitrate, glucose and urea, followed by in situ carbonization and reduction. The Co@CN/SiO2 catalysts were investigated for the selective reduction of nitro aromatics to the corresponding anilines using hydrazine hydrate. The Co@CN/SiO2-500 carbonized at 500 °C exhibited the highest catalytic activity and excellent stability without any decay of activity after 6 cycles for the reduction of nitrobenzene. Both metallic Co atoms and Co?N species formed in the Co@CN/SiO2 catalysts were active, but the Co?N species were dominant active sites. The high activities of the Co@CN/SiO2 catalysts were attributed to the synergistic effect between the Co and N atoms, promoting heterolytic cleavage of hydrazine to form H+/H? pairs. Representative examples demonstrated that the Co@CN/SiO2-500 could completely transform various halogen-substituted nitro aromatics to the corresponding halogenated anilines with high TOFs and selectivity of '99.5 percent.

Process route upstream and downstream products

Process route

2-bromo-5-fluoroaniline
1003-99-2

2-bromo-5-fluoroaniline

Conditions
Conditions Yield
Aus 2-Brom-5-fluor-acetanilid in wss. HCl;
Aus 2-Benzoylamino-1-brom-4-fluor-benzol, aethanol. HCl;
Aus 4-Fluor-1-brom-2-nitro-benzol in Eg. m. SnCl2 in konz. HCl;
2-bromo-5-fluoronitrobenzene
446-09-3

2-bromo-5-fluoronitrobenzene

2-bromo-5-fluoroaniline
1003-99-2

2-bromo-5-fluoroaniline

Conditions
Conditions Yield
2-bromo-5-fluoronitrobenzene; With iron; acetic acid; In ethanol; at 20 ℃; for 2.08333h; Heating / reflux;
With sodium hydroxide; In diethyl ether; water;
100%
With tin(ll) chloride; In ethanol; at 50 ℃; for 2h; Reagent/catalyst; Temperature;
100%
With iron; acetic acid; In ethanol; water; at 80 - 85 ℃; for 6h;
98.9%
With C36H56Cl3CrN2O; magnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In tetrahydrofuran; at 60 ℃; for 24h; chemoselective reaction; Inert atmosphere;
82%
With ammonium chloride; zinc; In water; at 80 ℃; for 0.5h;
68%
With hydrogen; nickel;
2-bromo-5-fluoronitrobenzene; With iron; acetic acid; In ethanol; for 2.08333h; Heating / reflux;
With sodium hydroxide; In diethyl ether; ethanol; water;
With hydrogen; hydrazine hydrate; In ethanol; at 40 ℃; for 1h; under 15001.5 Torr; chemoselective reaction; Catalytic behavior; Autoclave;
With hydrazine hydrate; In ethanol; at 30 ℃; for 1h; chemoselective reaction; Autoclave;
With hydrazine hydrate; In ethanol; at 70 ℃; for 1.16667h; chemoselective reaction; Catalytic behavior;
With hydrogen; In ethanol; at 80 ℃; for 1h; under 15001.5 Torr; chemoselective reaction; Catalytic behavior;
With hydrogen; In ethanol; at 120 ℃; for 3.5h; under 15001.5 Torr; Autoclave;
2-nitro-4-fluoroaniline
364-78-3

2-nitro-4-fluoroaniline

2-bromo-5-fluoroaniline
1003-99-2

2-bromo-5-fluoroaniline

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: HCl; aq. NaNO2 / 0 °C
1.2: CuBr; HCl / 0 - 60 °C
2.1: H2 / Raney Ni
With hydrogenchloride; hydrogen; sodium nitrite; nickel;
meta-fluoroaniline
372-19-0

meta-fluoroaniline

2-bromo-5-fluoroaniline
1003-99-2

2-bromo-5-fluoroaniline

3-fluoro-4-bromophenylamine
656-65-5

3-fluoro-4-bromophenylamine

Conditions
Conditions Yield
With N-Bromosuccinimide; In DCE; at 20 ℃;
89 %Chromat.
11 %Chromat.
1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

2-bromo-5-fluoroaniline
1003-99-2

2-bromo-5-fluoroaniline

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: sulfuric acid; nitric acid / water / 0.25 h / 0 °C
2: ammonium chloride; zinc / water / 0.5 h / 80 °C
With sulfuric acid; nitric acid; ammonium chloride; zinc; In water;
2-azido-1-bromo-5-fluorobenzene
909274-50-6

2-azido-1-bromo-5-fluorobenzene

2-bromo-5-fluoroaniline
1003-99-2

2-bromo-5-fluoroaniline

Conditions
Conditions Yield
With iron(III) oxide; hydrazine hydrate; In water; at 120 ℃; for 2.5h; Inert atmosphere;
81%
meta-fluoroaniline
372-19-0

meta-fluoroaniline

2-bromo-5-fluoroaniline
1003-99-2

2-bromo-5-fluoroaniline

Conditions
Conditions Yield
With hydrogen bromide; dimethyl sulfoxide; In ethyl acetate; at 60 ℃; for 12h;
4-fluoroaniline
371-40-4

4-fluoroaniline

2-bromo-5-fluoroaniline
1003-99-2

2-bromo-5-fluoroaniline

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: toluene / 2 h / 5 - 25 °C / Large scale
2.1: sulfuric acid / dichloromethane / 1 h / 0 - 5 °C
2.2: 1 h / 5 - 10 °C
3.1: sulfuric acid / water / 14 h / 75 - 80 °C
3.2: 1 h / 0 - 5 °C
3.3: 2 h / 40 - 50 °C
4.1: iron; acetic acid / water; ethanol / 6 h / 80 - 85 °C
With sulfuric acid; iron; acetic acid; In ethanol; dichloromethane; water; toluene;
4'-fluoroacetanilide
351-83-7

4'-fluoroacetanilide

2-bromo-5-fluoroaniline
1003-99-2

2-bromo-5-fluoroaniline

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: sulfuric acid / dichloromethane / 1 h / 0 - 5 °C
1.2: 1 h / 5 - 10 °C
2.1: sulfuric acid / water / 14 h / 75 - 80 °C
2.2: 1 h / 0 - 5 °C
2.3: 2 h / 40 - 50 °C
3.1: iron; acetic acid / water; ethanol / 6 h / 80 - 85 °C
With sulfuric acid; iron; acetic acid; In ethanol; dichloromethane; water;
2-bromo-5-fluoroaniline
1003-99-2

2-bromo-5-fluoroaniline

9-phenanthrenylboronic acid
68572-87-2

9-phenanthrenylboronic acid

C<sub>20</sub>H<sub>14</sub>FN

C20H14FN

Conditions
Conditions Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 80 ℃; for 12h; Inert atmosphere;

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