Gujral, Gurjeet’s team published research in Indian Journal of Heterocyclic Chemistry in 2021 | CAS: 624-28-2

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. Pyridine is very deactivated towards electrophilic substitution with respect to benzene. For this reason classical formylation, using methods such as the Gattermann or Vilsmeier reactions, are not generally successful. Synthetic Route of C5H3Br2N

Gujral, Gurjeet; Bhasin, K. K.; Gulati, Shivani published their research in Indian Journal of Heterocyclic Chemistry in 2021. The article was titled 《A new synthetic methodology for the preparation 2-Pyridyl anisyl/benzyl selenides: X-Ray Crystal Structure of 2-(4-Methyl pyridyl)tolyl selenide》.Synthetic Route of C5H3Br2N The article contains the following contents:

An effective methodol. for the synthesis of these selenides had been developed by reacting dianisyl/dibenzyl diselenide with substituted/unsubstituted 2-pyridyl halides in the presence of activated magnesium metal, Cu2O, and bipyridyl in DMF at 110°C for 18-20 h. The newly synthesized 2-pyridyl anisyl/benzyl selenides were either viscous liquids or crystalline solids that were stable at room temperature for several months without decomposition These were fully characterized by various spectroscopic techniques, namely, NMR (1H, 13C, and 77Se), IR, and mass spectroscopy. Single-crystal X-ray diffraction study of 2-(4-methylpyridyl) tolyl selenide was carried out to know the structural details of the mol. and well-defined diffraction quality crystals of 2-(4-Me pyridyl)tolyl selenide were obtained by slow evaporation of saturated solution of the compound in hexane-dichloromethane solvent mixture (4:1, volume/volume).2,5-Dibromopyridine(cas: 624-28-2Synthetic Route of C5H3Br2N) was used in this study.

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. Pyridine is very deactivated towards electrophilic substitution with respect to benzene. For this reason classical formylation, using methods such as the Gattermann or Vilsmeier reactions, are not generally successful. Synthetic Route of C5H3Br2N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Schaub, Tobias A.’s team published research in Journal of the American Chemical Society in 2020 | CAS: 624-28-2

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. Pyridines, quinolines, and isoquinolines have found a function in almost all aspects of organic chemistry. Pyridine has found use as a solvent, base, ligand, functional group, and molecular scaffold. As structural elements, these moieties are potent electron-deficient groups, metal-directing functionalities, fluorophores, and medicinally important pharmacophores. Reference of 2,5-Dibromopyridine

Reference of 2,5-DibromopyridineIn 2020 ,《Exploration of the Solid-State Sorption Properties of Shape-Persistent Macrocyclic Nanocarbons as Bulk Materials and Small Aggregates》 was published in Journal of the American Chemical Society. The article was written by Schaub, Tobias A.; Prantl, Ephraim A.; Kohn, Julia; Bursch, Markus; Marshall, Checkers R.; Leonhardt, Erik J.; Lovell, Terri C.; Zakharov, Lev N.; Brozek, Carl K.; Waldvogel, Siegfried R.; Grimme, Stefan; Jasti, Ramesh. The article contains the following contents:

Porous mol. materials combine benefits such as convenient processability and the possibility for atom-precise structural fine-tuning which makes them remarkable candidates for specialty applications in the areas of gas separation, catalysis, and sensing. In order to realize the full potential of these materials and guide future mol. design, knowledge of the transition from mol. properties into materials behavior is essential. In this work, the class of compounds termed cycloparaphenylenes (CPPs)-shape-persistent macrocycles with built-in cavities and radially oriented π-systems-was selected as a conceptually simple class of intrinsically porous nanocarbons to serve as a platform for studying the transition from analyte sorption properties of small aggregates to those of bulk materials. In our detailed investigation, two series of CPPs were probed: previously reported hoop-shaped [n]CPPs and a novel family of all-phenylene figure-8 shaped (lemniscal) bismacrocycles, termed spiro[n,n]CPPs. A series of nanocarbons with different macrocycle sizes and heteroatom content have been prepared by atom-precise organic synthetic methods, and their structural, photophys., and electronic attributes were disclosed. Detailed exptl. studies (X-ray crystallog., gas sorption, and quartz-crystal microbalance measurements) and quantum chem. calculations provided ample evidence for the importance of the solid-state arrangement on the porosity and analyte uptake ability of intrinsically porous mol. nanocarbons. We demonstrate that this mol. design principle, i.e., incorporation of sterically demanding spiro junctions into the backbone of nanohoops, enables the manipulation of solid-state morphol. without significantly changing the nature and size of the macrocyclic cavities. As a result, the novel spiro[n,n]CPPs showed a remarkable performance as high affinity material for vapor analyte sensing. The experimental process involved the reaction of 2,5-Dibromopyridine(cas: 624-28-2Reference of 2,5-Dibromopyridine)

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. Pyridines, quinolines, and isoquinolines have found a function in almost all aspects of organic chemistry. Pyridine has found use as a solvent, base, ligand, functional group, and molecular scaffold. As structural elements, these moieties are potent electron-deficient groups, metal-directing functionalities, fluorophores, and medicinally important pharmacophores. Reference of 2,5-Dibromopyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Cianfanelli, Marco’s team published research in Journal of the American Chemical Society in 2020 | CAS: 624-28-2

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. Pyridine is a relatively complex molecule and exhibits a number of different bands in IR spectra. Among others, the bands characterizing the ν8a and ν19b modes have been found to be sensitive to the coordination or protonation of the molecule. Note that the band that is diagnostic for the PyH+ ion at about 1545 cm− 1 (ν19b mode) does not overlap with any of the other bands.HPLC of Formula: 624-28-2

《Enantioselective C-H Lactonization of Unactivated Methylenes Directed by Carboxylic Acids》 was written by Cianfanelli, Marco; Olivo, Giorgio; Milan, Michela; Klein Gebbink, Robertus J. M.; Ribas, Xavi; Bietti, Massimo; Costas, Miquel. HPLC of Formula: 624-28-2 And the article was included in Journal of the American Chemical Society in 2020. The article conveys some information:

The formidable challenges of controlling site-selectivity, enantioselectivity, and product chemoselectivity make asym. C-H oxidation a generally unsolved problem for nonenzymic systems. Discrimination between the two enantiotopic C-H bonds of an unactivated methylenic group is particularly demanding and so far unprecedented, given the similarity between their environments and the facile overoxidn. of the initially formed hydroxylation product. Here we show that a Mn-catalyzed C-H oxidation directed by carboxylic acids can overcome these challenges to yield γ-lactones in high enantiomeric excess (up to 99%) using hydrogen peroxide as oxidant and a Bronsted acid additive under mild conditions and short reaction times. Coordination of the carboxylic acid group to the bulky Mn complex ensures the rigidity needed for high enantioselectivity and dictates the outstanding γ site-selectivity. When the substrate contains nonequivalent γ-methylenes, the site-selectivity for lactonization can be rationally predicted on the basis of simple C-H activation/deactivation effects exerted by proximal substituents. In addition, discrimination of diastereotopic C-H bonds can be modulated by catalyst design, with no erosion of enantiomeric excess. The potential of this reaction is illustrated in the concise synthesis of a tetrahydroxylated bicyclo[3.3.1]nonane enabled by two key, sequential γ-C-H lactonizations, with the latter that fixes the chirality of five stereogenic centers in one step with 96% ee. In the part of experimental materials, we found many familiar compounds, such as 2,5-Dibromopyridine(cas: 624-28-2HPLC of Formula: 624-28-2)

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. Pyridine is a relatively complex molecule and exhibits a number of different bands in IR spectra. Among others, the bands characterizing the ν8a and ν19b modes have been found to be sensitive to the coordination or protonation of the molecule. Note that the band that is diagnostic for the PyH+ ion at about 1545 cm− 1 (ν19b mode) does not overlap with any of the other bands.HPLC of Formula: 624-28-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Siddique, Rashid G.’s team published research in Angewandte Chemie, International Edition in 2022 | CAS: 624-28-2

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. Pyridine and pyridine-derived structures are privileged pharmacophores in medicinal chemistry and an essential functionality for organic chemists. As the prototypical π-deficient heterocycle, pyridine illustrates distinctive chemistry as both substrate and reagent. Safety of 2,5-Dibromopyridine

Safety of 2,5-DibromopyridineIn 2022 ,《Controlling the Complexity and Interconversion Mechanisms in Self-Assembled [Fe2L3]4+ Helicates and [Fe4L6]8+ Cages》 was published in Angewandte Chemie, International Edition. The article was written by Siddique, Rashid G.; Arachchige, Kasun S. A.; Al-Fayaad, Hydar A.; Thoburn, John D.; McMurtrie, John C.; Clegg, Jack K.. The article contains the following contents:

Self-assembled coordination cages and metal-organic frameworks have relied extensively on sym. ligands in their formation. Here the authors prepared a relatively simple system employing an unsym. ligand that results in two distinct self-assembled structures, a [Fe2L3]4+ helicate and a [Fe4L6]8+ cage composed of 10 interconverting diastereomers and their enantiomers. The steric profile of the ligand controls the complexity, thermodn. and kinetics of interconversion of the system. In the experiment, the researchers used 2,5-Dibromopyridine(cas: 624-28-2Safety of 2,5-Dibromopyridine)

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. Pyridine and pyridine-derived structures are privileged pharmacophores in medicinal chemistry and an essential functionality for organic chemists. As the prototypical π-deficient heterocycle, pyridine illustrates distinctive chemistry as both substrate and reagent. Safety of 2,5-Dibromopyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reddivari, Chenna Krishna Reddy’s team published research in Polycyclic Aromatic Compounds in 2022 | CAS: 624-28-2

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. In industry and in the lab, pyridine is used as a reaction solvent, particularly when its basicity is useful, and as a starting material for synthesizing some herbicides, fungicides, and antiseptics.Application of 624-28-2

In 2022,Reddivari, Chenna Krishna Reddy; Devineni, Subba Rao; Nemallapudi, Bakthavatchala Reddy; Sravya, Gundala; Avula, Balakrishna; Shaik, Nayabrasool; Badavath, Vishnu Nayak; Zyryanov, Grigory V.; YellalaVenkata, Rami Reddy; Chamarthi, Naga Raju published an article in Polycyclic Aromatic Compounds. The title of the article was 《Design, Synthesis, Biological Evaluation and Molecular Docking Studies of 1,4-Disubstituted 1,2,3-Triazoles: PEG-400:H2O Mediated Click Reaction of Fluorescent Organic Probes under Ultrasonic Irradiation》.Application of 624-28-2 The author mentioned the following in the article:

A PEG-400:H2O mediated highly versatile, efficacious and selective “”Click reaction”” of fluorescent organic Probes under ultrasonic irradiation were reported. A rapid and efficient approach for the synthesis of 1,4-Disubstituted 1,2,3-triazoles I [R = (4-fluorophenyl)methyl, 2,4-dioxo-pyrimidin-5-yl, etc.] under Copper (I)-Catalyzed Azide-Alkyne [3 + 2] Cycloaddition (CuAAC) conditions in good to excellent yields in less time were described. This synthetic protocol were proved to endorse easy work-up under benign reaction conditions. The green solvent system employed was efficaciously reused several times without any loss of its activity in an aqueous medium. All the title compounds were characterized by using elemental anal., 1HNMR, 13CNMR, FTIR, and mass spectral data. The newly synthesized compounds were biol. evaluated for their antioxidant activity. The antioxidant activity resulted demonstrate that all compounds showed good to excellent antioxidant activity, particularly the compounds I [R = (4-bromophenyl)methyl, 5-bromo-2-pyridyl, pyrimidin-2-yl, 2,4-dioxo-pyrimidin-5-yl] exhibited promising radical scavenging activity. Further, photophys. properties of the compounds were accomplished using spectrofluorimeter. Compounds I [R = (3-chlorophenyl)methyl, (4-nitrophenyl)methyl, (4-cyanophenyl)methyl, thiazol-2-yl, 5-bromo-2-pyridyl, pyrimidin-2-yl, 2,4-dioxo-pyrimidin-5-yl] exhibited fluorescence in the visible region. Mol. docking studies suggested the antioxidant activity of synthesized compounds were due to the inhibition of neuronal nitric oxide synthase (HnNOS). In the experiment, the researchers used 2,5-Dibromopyridine(cas: 624-28-2Application of 624-28-2)

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. In industry and in the lab, pyridine is used as a reaction solvent, particularly when its basicity is useful, and as a starting material for synthesizing some herbicides, fungicides, and antiseptics.Application of 624-28-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Hylland, Knut Tormodssoenn’s team published research in European Journal of Organic Chemistry in 2020 | CAS: 624-28-2

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. In industry and in the lab, pyridine is used as a reaction solvent, particularly when its basicity is useful, and as a starting material for synthesizing some herbicides, fungicides, and antiseptics.Computed Properties of C5H3Br2N

《The Suzuki-Miyaura Cross-Coupling as the Key Step in the Synthesis of 2-Aminobiphenyls and 2,2′-Diaminobiphenyls: Application in the Synthesis of Schiff Base Complexes of Zn》 was published in European Journal of Organic Chemistry in 2020. These research results belong to Hylland, Knut Tormodssoenn; Oien-Odegaard, Sigurd; Tilset, Mats. Computed Properties of C5H3Br2N The article mentions the following:

2-Nitrophenylboronic acids serve as interesting starting materials for the construction of biphenyl- and terphenyl-based amines if subjected to the Suzuki-Miyaura reaction. Unfortunately, these boronic acids suffer from low reactivity in Suzuki reactions, alongside their low stability in the presence of Pd. Herein, a general method for the construction of 2-nitro-substituted bi- and terphenyls is presented, with special emphasis on the synthesis of 2-amino-2′-nitrobi- and terphenyls. Comparisons are made with other boronic acids that have some of the aforementioned issues. Finally, the application of the obtained 2-amino-2′-nitrobi- and terphenyls as starting materials for the synthesis of bi- and terphenyl based di- and triamines is encountered for, with emphasis on the use of these amines as precursors for Schiff base ligands. In addition, the synthesis of some Zn complexes of these ligands is presented. In the part of experimental materials, we found many familiar compounds, such as 2,5-Dibromopyridine(cas: 624-28-2Computed Properties of C5H3Br2N)

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. In industry and in the lab, pyridine is used as a reaction solvent, particularly when its basicity is useful, and as a starting material for synthesizing some herbicides, fungicides, and antiseptics.Computed Properties of C5H3Br2N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Siddique, Rashid G.’s team published research in Chemical Communications (Cambridge, United Kingdom) in 2021 | CAS: 624-28-2

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. Pyridine is a relatively complex molecule and exhibits a number of different bands in IR spectra. Among others, the bands characterizing the ν8a and ν19b modes have been found to be sensitive to the coordination or protonation of the molecule. Note that the band that is diagnostic for the PyH+ ion at about 1545 cm− 1 (ν19b mode) does not overlap with any of the other bands.Recommanded Product: 624-28-2

Siddique, Rashid G.; Arachchige, Kasun S. A.; AL-Fayaad, Hydar A.; Brock, Aidan J.; Micallef, Aaron S.; Luis, Ena T.; Thoburn, John D.; McMurtrie, John C.; Clegg, Jack K. published an article in 2021. The article was titled 《The kinetics and mechanism of interconversion within a system of [Fe2L3]4+ helicates and [Fe4L6]8+ cages》, and you may find the article in Chemical Communications (Cambridge, United Kingdom).Recommanded Product: 624-28-2 The information in the text is summarized as follows:

Nature builds simple mols. into highly complex assemblies, which are involved in all fundamental processes of life. Some of the most intriguing biol. assemblies are those that can be precisely reconfigured to achieve different functions using the same building blocks. Understanding the reconfiguration of synthetic self-assembled systems will allow us to better understand the complexity of proteins and design useful artificial chem. systems. Here the authors prepared a relatively simple system in which two distinct self-assembled structures, a [Fe2L3]4+ helicate and a [Fe4L6]8+ cage that are formed from the same precursors, coexist at equilibrium, L is bisbipyrinyldiethynylbenzene. The authors measured the rates of interconversion of these two species and propose a mechanism for the transformation. The results came from multiple reactions, including the reaction of 2,5-Dibromopyridine(cas: 624-28-2Recommanded Product: 624-28-2)

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. Pyridine is a relatively complex molecule and exhibits a number of different bands in IR spectra. Among others, the bands characterizing the ν8a and ν19b modes have been found to be sensitive to the coordination or protonation of the molecule. Note that the band that is diagnostic for the PyH+ ion at about 1545 cm− 1 (ν19b mode) does not overlap with any of the other bands.Recommanded Product: 624-28-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Xu, Shaoyi’s team published research in Journal of Materials Chemistry A: Materials for Energy and Sustainability in 2020 | CAS: 624-28-2

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. Pyridine and its simple derivatives are stable and relatively unreactive liquids, with strong penetrating odours that are unpleasant.Related Products of 624-28-2

《Understanding the role of acid-base interactions using architecturally-controlled, pyridyl-bearing sulfonated phenylated polyphenylenes》 was published in Journal of Materials Chemistry A: Materials for Energy and Sustainability in 2020. These research results belong to Xu, Shaoyi; Wu, Yang; Adamski, Michael; Fraser, Kate; Holdcroft, Steven. Related Products of 624-28-2 The article mentions the following:

Acid-base interactions between N-heterocycles and sulfonic acid groups are known to mitigate the excessive swelling of hydrocarbon-based proton exchange polymers, but concurrently reduce the concentration of hydrated protons therein, which lowers proton conductivity We report sulfonated phenylated poly(phenylene) homopolymers designed with similar architecture but with an increasing number of strategically-placed N-atoms in the form of pyridyl units. It is discovered that polymers with 2 or more pyridines per repeat unit do not stoichiometrically neutralize pendent sulfonic acids. For example, four pyridines per repeat unit neutralize the equivalent of ~2 sulfonic acids, resulting in a reduced number of pyridinium (H+)-sulfonate cross links than anticipated. DFT calculations reveal that externally-exposed pyridine groups form a stronger interaction with protons than a sterically-hindered pyridine that affects mech. properties and water sorption. Nonetheless, as the number of N-atoms is increased, the fraction of neutralized -SO3H protons is increased, and the material’s ion exchange capacity, proton conductivity, liquid and vaporous water sorption, dimensional swelling, steady-state water permeability, and transient diffusivity all decrease. With four pyridyl groups per repeating unit, dimensional swelling of the fully hydrated polymer, steady-state water permeability are similar to the Nafion N211 reference material. However, proton conductivities under reduced RH are substantially reduced due to their low water sorption. This work provides insight into tailoring proton exchange membranes via acid-base, self-neutralization for the purpose of controlling their transport properties.2,5-Dibromopyridine(cas: 624-28-2Related Products of 624-28-2) was used in this study.

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. Pyridine and its simple derivatives are stable and relatively unreactive liquids, with strong penetrating odours that are unpleasant.Related Products of 624-28-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Liu, Lunjie’s team published research in Journal of Materials Chemistry A: Materials for Energy and Sustainability in 2021 | CAS: 624-28-2

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. Pyridine and its simple derivatives are stable and relatively unreactive liquids, with strong penetrating odours that are unpleasant.Synthetic Route of C5H3Br2N

《Acetylene-linked conjugated polymers for sacrificial photocatalytic hydrogen evolution from water》 was written by Liu, Lunjie; Kochman, Michal A.; Xu, Yongjie; Zwijnenburg, Martijn A.; Cooper, Andrew I.; Sprick, Reiner Sebastian. Synthetic Route of C5H3Br2N And the article was included in Journal of Materials Chemistry A: Materials for Energy and Sustainability in 2021. The article conveys some information:

Conjugated organic polymers have shown potential as photocatalysts for hydrogen production by water splitting. Taking advantage of a high throughput screening workflow, two series of acetylene-linked co-polymers were prepared and studied for their potential as photocatalysts for sacrificial hydrogen production from water. It was found that a triethynylbenzene-based polymer with a dibenzo[b,d]thiophene sulfone linker (TE11) had the highest performance in terms of hydrogen evolution rate under visible illumination in the presence of a sacrificial hole-scavenger. Synthetically elaborating the triethynylbenzene linker in TE11 by changing the core and by introducing nitrogen, the resulting hydrogen evolution rate was further increased by a factor of nearly two. The experimental part of the paper was very detailed, including the reaction process of 2,5-Dibromopyridine(cas: 624-28-2Synthetic Route of C5H3Br2N)

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. Pyridine and its simple derivatives are stable and relatively unreactive liquids, with strong penetrating odours that are unpleasant.Synthetic Route of C5H3Br2N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Zhang, Guobing’s team published research in Journal of Materials Chemistry C: Materials for Optical and Electronic Devices in 2021 | CAS: 624-28-2

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. In industry and in the lab, pyridine is used as a reaction solvent, particularly when its basicity is useful, and as a starting material for synthesizing some herbicides, fungicides, and antiseptics.Reference of 2,5-Dibromopyridine

Zhang, Guobing; Yu, Hao; Sun, Yue; Wang, Weiwei; Zhao, Yao; Wang, Lichun; Qiu, Longzhen; Ding, Yunsheng published their research in Journal of Materials Chemistry C: Materials for Optical and Electronic Devices in 2021. The article was titled 《Aza-substitution on naphthalene diimide-based conjugated polymers for n-type bottom gate/top contact polymer transistors under ambient conditions》.Reference of 2,5-Dibromopyridine The article contains the following contents:

Four conjugated polymers based on naphthalene diimide (NDI) as the acceptor and thiophene-phenyl-thiophene with different aza-substitutions as co-units were synthesized. The aza-substitution gradually lowered the HOMO (HOMO) and the LUMO (LUMO) energy levels. The polymer with four aza-substitutions exhibited the deepest LUMO/HOMO energy level (-4.10/-6.01 eV). Consequently, organic field-effect transistors (OFETs) based on the bottom-gate/top-contact configuration exhibited unipolar electron transport characteristics even if the devices were exposed directly to ambient conditions. Furthermore, the corresponding devices also maintained their n-type transport behavior during long-term storage in air (>300 days). This work demonstrated that the incorporation of nitrogen atoms into NDI-based conjugated polymers for further lowering the energy levels is a feasible strategy for the construction of air-stable n-type unencapsulated OFETs. After reading the article, we found that the author used 2,5-Dibromopyridine(cas: 624-28-2Reference of 2,5-Dibromopyridine)

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. In industry and in the lab, pyridine is used as a reaction solvent, particularly when its basicity is useful, and as a starting material for synthesizing some herbicides, fungicides, and antiseptics.Reference of 2,5-Dibromopyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem