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2-Fluoroaniline, with the CAS number 348-54-9, is a derivative of aniline where the hydrogen at position 2 has been replaced by a fluorine atom. It is a primary arylamine and a fluoroaniline, characterized as a clear colorless to brown liquid with a mild sweet odor. It is toxic, insoluble in water, and soluble in ethanol and ether. Its vapor and air can form an explosive mixture, which can cause combustion and explosion in case of fire and high heat. It reacts with oxidants and decomposes under high heat to release toxic gases.

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348-54-9 Usage

Uses

Used in Pharmaceutical Industry:
2-Fluoroaniline is utilized as a pharmaceutical intermediate due to its unique chemical properties, contributing to the development of various medications.
Used in Chemical Synthesis:
2-Fluoroaniline serves as a useful reagent for the synthesis of insecticides, playing a crucial role in the development of effective pest control solutions.
Used in Printing Industry:
2-Fluoroaniline can be used to synthesize thermosensitive dye FH-102, a black thermosensitive dye with wide application and excellent performance. This dye is employed in the production of terminal output printing paper for electronic computers, EEG recording paper, telephone fax paper, and transparent thermal film for oil fields, enhancing the functionality and efficiency of these products.

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 3415, 1984 DOI: 10.1016/S0040-4039(01)91034-2

Air & Water Reactions

Water soluble.

Reactivity Profile

2-Fluoroaniline is a base. Neutralizes acids to form salts plus water in an exothermic reaction. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Health Hazard

Inhalation or ingestion causes bluish tint to fingernails, lips and ears indicative of cyanosis; headache, drowsiness, and nausea, followed by unconsciousness. Liquid can be absorbed through skin and cause similar symptoms. Contact with eyes causes irritation.

Fire Hazard

Special Hazards of Combustion Products: Irritating and toxic hydrogen fluoride and oxides of nitrogen may form in fires.

Metabolic pathway

2-Fluoro and 3-fluoroanilines are preferentially hydroxylated at the para-position, and 4-fluoroaniline is both p- and o-hydroxylated to a significant extent by rat liver microsomes and is not accompanied with an NIH shift to give 4-hydroxyl-3-fluoroaniline.

Check Digit Verification of cas no

The CAS Registry Mumber 348-54-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,4 and 8 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 348-54:
(5*3)+(4*4)+(3*8)+(2*5)+(1*4)=69
69 % 10 = 9
So 348-54-9 is a valid CAS Registry Number.
InChI:InChI=1/C6H6FN/c7-5-3-1-2-4-6(5)8/h1-4H,8H2

348-54-9 Well-known Company Product Price

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  • Alfa Aesar

  • (A12612)  2-Fluoroaniline, 99%   

  • 348-54-9

  • 25g

  • 186.0CNY

  • Detail
  • Alfa Aesar

  • (A12612)  2-Fluoroaniline, 99%   

  • 348-54-9

  • 100g

  • 460.0CNY

  • Detail
  • Alfa Aesar

  • (A12612)  2-Fluoroaniline, 99%   

  • 348-54-9

  • 500g

  • 1583.0CNY

  • Detail

348-54-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-fluoroaniline

1.2 Other means of identification

Product number -
Other names ortho-fluoroaniline

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:348-54-9 SDS

348-54-9Synthetic route

ortho-nitrofluorobenzene
1493-27-2

ortho-nitrofluorobenzene

2-Fluoroaniline
348-54-9

2-Fluoroaniline

Conditions
ConditionsYield
With ammonium hydroxide; hydrogen In methanol; water at 50℃; under 750.075 Torr; for 8h;99.6%
With hydrogen In neat (no solvent) at 59.84℃; under 30003 Torr; for 1.5h; Autoclave;99%
With hydrogen In ethanol; water at 130℃; under 7500.75 Torr; for 3h; Autoclave;99%
1-Fluoro-2-iodobenzene
348-52-7

1-Fluoro-2-iodobenzene

2-Fluoroaniline
348-54-9

2-Fluoroaniline

Conditions
ConditionsYield
With ammonium hydroxide; potassium phosphate; 1-(5,6,7,8-tetrahydroquinolin-8-yl)-2-methylpropan-1-one; copper(I) bromide In dimethyl sulfoxide at 25℃; for 24h; Inert atmosphere; Sealed tube;93%

348-54-9Relevant academic research and scientific papers

Synthesis of Pd/SBA-15 catalyst employing surface-bonded vinyl as a reductant and its application in the hydrogenation of nitroarenes

Duan, Ying,Zheng, Min,Li, Dongmi,Deng, Dongsheng,Wu, Cuicui,Yang, Yanliang

, p. 3443 - 3449 (2017)

The Pd/SBA-15 catalyst was synthesised through the reduction of PdCl2 by the surface-bonded vinyl group on vinyl-functionalized SBA-15, which was prepared via co-polymerization. XRD and XPS characterization confirmed the successful reduction of Pd(ii) to Pd(0). Pd/SBA-15 showed a narrow palladium particle-size distribution of about 5-6 nm in the TEM image. The Pd/SBA-15 catalyst was effective for the hydrogenation of aromatic nitro compounds with zero-order kinetics, and the TOF for the hydrogenation of nitrobenzene was 1124 h-1 at 313 K and 1 atm H2. A steric effect was observed for the substituted nitroarenes.

Photocatalytic hydrogenation of nitroarenes: supporting effect of CoOx on TiO2 nanoparticles

Amanchi, Srinivasa Rao,Ashok Kumar,Lakshminarayana, Bhairi,Satyanarayana,Subrahmanyam

, p. 748 - 754 (2019)

Cobalt oxide visible light-active photo-catalysts supported on TiO2 nanoparticles with varying amount of cobalt oxide [3% CoOx/TiO2 (A), 4% CoOx/TiO2 (B), 5% CoOx/TiO2 (C)] were synthesized by solid-state method followed by calcination. The as-synthesized catalysts were characterized by various techniques such as powder XRD, TEM, EDX, UV-Vis-DRS and XPS analysis. The photocatalytic activity of the as-synthesized materials was studied for the reduction of nitroarenes to the corresponding amines using hydrazine monohydrate as the reductant. Cobalt(ii) oxide is responsible for the reduction of nitroarenes and then, cobalt(iii) is reduced back to the original compound by hydrazine hydrate, thus ascertaining the catalytic nature of this hydrogenation process. XPS suggests the presence of Co(ii) in CoOx/TiO2.

Role of Charge Transfer in Nucleophilic Substitution Reactions in Clusters of 1-Fluoro-n-chlorobenzene Cations with Ammonia Molecules

Riehn, C.,Lahmann, C.,Brutschy, B.

, p. 3626 - 3632 (1992)

The reaction behavior of mixed clusters consisting of fluorochlorobenzene radical cations surrounded by ammonia molecules has been studied by resonant two-photon ionization.The spectral characterization of the neutral precursors allows one to study ion reactions in the cluster with a well-defined microsolvation environment.In addition to charge transfer, two types of nucleophilic substitution reactions take place.In a binary complex chlorine is ejected either in an ipso substitution by radical loss or, for meta and para isomers, by HCl formation, in the latter case by a metastable decay.The reaction efficiency for Cl elimination decreases with decreasing dipole moment of the chromophore.It is rationalized by a ? addition intermediate with an activation barrier due to charge transfer as postulated by the model of Shaik and Pross.The HCl elimination is not rate determined by the formation of a ? intermediate.In ternary and larger mixed complexes mainly substitution of fluorine takes place with HF as leaving group, corresponding to the onset of solvation catalysis.

Aminal-based Hypercrosslinked Polymer Modified with Small Palladium Nanoparticles for Efficiently Catalytic Reduction of Nitroarenes

Xu, Dan,Wang, Fushan,Yu, Guiqin,Zhao, Hong,Yang, Jing,Yuan, Man,Zhang, Xiaoyun,Dong, Zhengping

, p. 4569 - 4577 (2018)

Fabrication of heterogeneous catalysts with excellent activity, selectivity and stability is significant for various catalytic applications. Here, we prepared a hypercrosslinked polymer (HCP) via a facile and cost-effective strategy using ferrocenecarboxaldehyde and melamine as building blocks. Then, the HCP was modified with highly dispersed ultrafine Pd nanoparticles (Pd/HCP). The obtained Pd/HCP shows excellent catalytic activity in the catalytic reduction of nitroarenes under mild reaction conditions. It′s worth mentioning that the N atoms in the HCP can efficiently coordinate Pd ions to form small Pd nanoparticles (NPs) and subsequently prevent the aggregation and leaching of Pd NPs during the reaction, so the Pd/HCP catalyst is highly stable and can be reused at least eight cycles without loss of catalytic activity. Therefore, this work may provide possibilities for using HCPs as ideal supporting materials for fabricating highly stable and efficient heterogeneous catalysts.

A Radical-Mediated Approach to the Total Synthesis of Fluorinated Marinoquinoline A and Related Tricyclic and Tetracyclic Congeners

Patel, Bhaven,Hilton, Stephen T.

, p. 79 - 83 (2015)

A radical-mediated approach to the core structure of fluorinated marinoquinoline A, N-methylated marinoquinoline A and related congeners via the use of Togni's reagent is described.

Highly selective hydrogenation of halonitroaromatics to aromatic haloamines by ligand modified Ni-based catalysts

Lu, Chun Shan,Lv, Jing Hui,Ma, Lei,Zhang, Qun Feng,Feng, Feng,Li, Xiao Nian

, p. 545 - 548 (2012)

Ligand modification of Ni-based catalysts by coordination of dicyandiamide to Ni metal leads to enhanced selectivity for the selective hydrogenation of halonitroaromatics. The selectivity of above 99.9% to aromatic haloamines can be achieved at the conversion of 100%. The results of H2-TPD and FT-IR experiments show that Ni-H+ species possessing the properties of Lewis acid site on the surface of Raney Ni could be responsible for the hydrodehalogenation. When Raney Ni was treated by dicyandiamide, Ni -H+ species interacted with N atom from the dicyandiamide. This interaction was stable even at reaction temperature, which reduced the possibility to form the intermediate state of ArCl?H+Ni -. And then CCl bond could not be polarized and activated. The hydrodechlorination process was suppressed effectively.

PVA-encapsulated Palladium Nanoparticles: Eco-friendly and Highly Selective Catalyst for Hydrogenation of Nitrobenzene in Aqueous Medium

Wang, Xiaoyan,Huang, Changru,Li, Xiaohao,Xie, Congxia,Yu, Shitao

, p. 2266 - 2272 (2019)

In aqueous medium without any other additives, palladium (Pd) nanoparticles with water-soluble polyvinyl alcohol (PVA) as stabilizer were synthesized for the catalytic hydrogenation of nitrobenzene. Under the optimum experimental conditions, the nitrobenzene conversion and the selectivity for aniline were 99.3 % and 100 %, respectively. Comprehensive characterization methods, including TEM, UV/Vis, confocal laser scanning microscopy (CLSM), XRD and XPS allowed a better understanding of the role of PVA aggregates and the properties of Pd nanoparticles. The nitrobenzene conversion exceeded 80 % even after 6 cycles without any treatment of the catalyst. A mechanism about the hydrogenation of nitrobenzene catalyzed by Pd/PVA system was proposed. The Pd/PVA catalyst also exhibited excellent activity and selectivity, particularly to ortho-fluoronitrobenzene and ortho-nitrotoluene. This research can provide a reference for the environmentally friendly catalysis for hydrogenation of nitrobenzene and other substituted nitrobenzene compounds.

Synthesis of Pt nanocatalysts for selective hydrogenation of ortho-halogenated nitrobenzene

Xie, Ruigang,Cao, Xueqin,Pan, Yue,Gu, Hongwei

, p. 1051 - 1055 (2015)

Monodisperse Pt nanoparticles (NPs) were prepared by reduction of platinum acetylacetonate in octadecene with the presence of Fe(CO)5. The synthesized nanocatalysts presented high activity and selectively for hydrogenation of ortho-halogenated nitrobenzene to the corresponding ortho-halogenated aniline under mild reaction conditions.

In situcreation of multi-metallic species inside porous silicate materials with tunable catalytic properties

Liu, Yang-Yang,Wu, Chuan-De,Zhan, Guo-Peng

supporting information, p. 6185 - 6188 (2021/06/30)

Porous metal silicate (PMS) material PMS-11, consisting of uniformly distributed multi-metallic species inside the pores, is synthesized by using a discrete multi-metal coordination complex as the template, demonstrating high catalytic activity and selectivity in hydrogenation of halogenated nitrobenzenes by synergistically activating different reactant moleculesviaNi and Co transition metal centers, while GdIIILewis acid sites play a role in tuning the catalytic properties.

A suitable modified palladium immobilized on imidazolium supported ionic liquid catalysed transfer hydrogenation of nitroarenes

Atheeswari, Alagudurai,Kanimozhi, Nallusamy,Karthikeyan, Parasuraman,Shanmugapriya, Ramasamy

, (2021/06/28)

The first well-defined modified palladium immobilized on imidazolium supported ionic liquid catalyst has been developed for the transfer hydrogenation of nitroarenes to anilines in good to excellent yields with formic acid as reducing agent. This methodology applies eco-friendly a reducing agent which is non-toxic, water soluble, more stable and simpler to handle. Particularly, the process constitutes a rare model of base-free transfer hydrogenations. The catalyst was reused up to nine consecutive cycles without any significance loss in its activity.

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