78583-82-1

Basic information

• Product Name: 5-(4-BROMOPHENYL)-2H-PYRAZOL-3-YLAMINE
• Synonyms: 3-Amino-5-(4-bromophenyl)-1H-pyrazole;5-Amino-3-(4-bromophenyl)-1H-pyrazole;3-(4-Bromophenyl)-1H-pyrazol-5-amine, 5-(4-Bromophenyl)-2H-pyrazol-3-amine;SALOR-INT L317861-1EA;5-(4-BROMOPHENYL)-2H-PYRAZOL-3-YLAMINE;5-AMINO-3-(4-BROMOPHENYL)PYRAZOLE;3-(4-BROMOPHENYL)-1H-PYRAZOL-5-AMINE
• CAS NO: 78583-82-1
• Molecular Formula: C₉H₈BrN₃
• Molecular Weight: 238.08
• Product Categories: Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrazoles;PyrazolesHeterocyclic Building Blocks
• Mol File: 78583-82-1.mol

Chemical Properties

• Melting Point: 172-176 °C(lit.)
• Boiling Point: 485.1°C at 760 mmHg
• Flash Point: 247.2°C
• Appearance: /
• Density: 1.645g/cm³
• Vapor Pressure: 1.45E-09mmHg at 25°C
• Refractive Index: 1.689
• PKA: 14.08±0.10(Predicted)
• CAS DataBase Reference: 5-(4-BROMOPHENYL)-2H-PYRAZOL-3-YLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-BROMOPHENYL)-2H-PYRAZOL-3-YLAMINE(78583-82-1)
• EPA Substance Registry System: 5-(4-BROMOPHENYL)-2H-PYRAZOL-3-YLAMINE(78583-82-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 78583-82-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
5-(4-BROMOPHENYL)-2H-PYRAZOL-3-YLAMINE is used as a building block for the synthesis of biologically active compounds, playing a crucial role in the development of new pharmaceuticals.
Used in the Treatment of Inflammatory Diseases:
In the medical field, 5-(4-BROMOPHENYL)-2H-PYRAZOL-3-YLAMINE is used as a potential therapeutic agent for inflammatory diseases, leveraging its capacity to modulate immune responses and reduce inflammation.
Used in Cancer Treatment:
5-(4-BROMOPHENYL)-2H-PYRAZOL-3-YLAMINE is also being studied for its potential in treating cancer due to its ability to interact with cellular processes that contribute to tumor growth and progression.
Used as a Reagent in Chemical Reactions:
In the chemical industry, 5-(4-BROMOPHENYL)-2H-PYRAZOL-3-YLAMINE serves as a reagent, facilitating various chemical processes and reactions due to its reactive functional groups.
Used as a Ligand in Coordination Chemistry:
5-(4-BROMOPHENYL)-2H-PYRAZOL-3-YLAMINE is utilized as a ligand in coordination chemistry, where it forms complexes with metal ions, contributing to the study and application of coordination compounds in diverse areas.

InChI:InChI=1/C9H8BrN3/c10-7-3-1-6(2-4-7)8-5-9(11)13-12-8/h1-5H,(H3,11,12,13)

Upstream product

• 78583-87-6 (E)-3-(4-Bromo-phenyl)-3-chloro-acrylonitrile 
• 4592-94-3 3-(4-bromophenyl)-3-oxopropanenitrile 
• 1122-91-4 4-bromo-benzaldehyde 
• 586-76-5 4-Bromobenzoic acid 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 936368-52-4 (Z)-3-(4-bromophenyl)-3-chloro-2-propenenitrile 
• 14063-78-6 3-(4-bromophenyl)-3-chloroprop-2-enal 
• 99-90-1 para-bromoacetophenone 

Downstream Products

• 149246-94-6 2-(4-Bromo-phenyl)-4H-pyrazolo[1,5-a]pyrimidin-7-one 

Relevant articles and documents

Synthesis and structure–activity relationships of pyrazolo-[3,4-b]pyridine derivatives as adenosine 5'-monophosphate-activated protein kinase activators

A series of pyrazolo[3,4-b]pyridine derivatives were designed, synthesized, and evaluated for their activation activity toward adenosine 5'-monophosphate-activated protein kinase (AMPK). According to the enzyme activity, the pyrazole N?H exposure and para substitution on the diphenyl group were proved to be essential for the activation potency. Compound 17f showed equal activation compared with A-769662. In the molecular modeling study, compound 17f exhibited important hydrogen bond interaction with Lys29, Asp88, and Arg83. 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assays on the NRK-49F cell line showed that potent enzyme activators could effectively inhibit cell proliferation, especially for 17f (EC50 [AMPKα1γ1β1] = 0.42 μM, efficacy = 79%; IC50 [NRK-49F cell line] = 0.78 μM). These results might provide new insights to explore novel AMPK activators.

3-[5-(4-Bromophenyl)-1H-pyrazol-3-ylamino]-5,5-dimethylcyclohex-2-en-1-one- (Z)-3-(4-bromophenyl)-3-chloroacrylonitrile (2/1): A stoichiometric cocrystal of a reaction product with one of its early precursors

The title compound, 2C17H18BrN3O· C9H5BrClN, was crystallized from the reaction between 5,5-dimethylcyclohexane-1,3-dione, triethyl orthoformate and 5-amino-3-(4-bromophenyl)pyrazole, which had itself been prepared from the reaction between (Z)-3-(4-bromophenyl)-3-chloroacrylonitrile and hydrazine. The compound is a stoichiometric 2:1 cocrystal of the reaction product 3-[5-(4-bromophenyl)-1H-pyrazol-3-ylamino]-5,5-dimethylcyclohex-2-en-1-one and the early reactant (Z)-3-(4-bromophenyl)-3-chloroacrylonitrile. The two independent molecules of cyclohex-2-en-1-one are linked by N-H...N and N-H...O hydrogen bonds into complex bilayers and the molecules of acrylonitrile are trapped within large cavities in the substructure formed by the cyclohex-2-en-1-one molecules.

Novel benzenesulfonamide-bearing pyrazoles and 1,2,4-thiadiazoles as selective carbonic anhydrase inhibitors

Two series comprising 20 novel benzenesulfonamides bearing thioureido-linked pyrazole 8 and amino-1,2,4-thiadiazole 10 were synthesized and assayed as human carbonic anhydrase (hCA) inhibitors against isoforms I and II as well as the tumor-associated isof

Synthesis of Pyrazole Compounds by Using Sonication Method

A simple method for the synthesis of pyrazoles derivatives carried out by cyclization of cyanide with hydrazine hydrate by using sonication method. All the prepared compounds were characterized by 1H, 13C NMR and IR Spectroscopy.

Modular synthesis and antiproliferative activity of new dihydro-1H-pyrazolo[1,3-b]pyridine embelin derivatives

A set of new dihydro-1H-pyrazolo[1,3-b]pyridine and pyrazolo[1,3-b]pyridine embelin derivatives was synthesized through a multicomponent reaction from natural embelin, 3-substituted-5-aminopyrazoles and aldehydes. The synthesized compounds were evaluated against three hematologic tumor cell lines, HEL (acute erythroid leukemia), K-562 (chronic myeloid leukemia) and HL-60 (acute myeloid leukemia), and five breast cancer cell lines (SKBR3, MCF-7, MDA-MB-231, BT-549, HS-578T). The primate non-malignant kidney Vero cell line was used as the control of cytotoxicity. From the obtained results, some structure–activity relationships were out-lined. Furthermore, in silico prediction of physicochemical properties and ADME parameters were determined for the derivatives with the best antiproliferative values.

Synthesis of pyrazolopyrimidinones using a “one-pot” approach under microwave irradiation

A simple one-pot method for the microwave-assisted synthesis of substituted pyrazolo[1,5-a]pyrimidinones, a core scaffold in many bioactive and pharmaceutically relevant compounds, has been established. A variety of substituents was tolerated at the 2 and 5 positions, including functionalized aryls, heterocycles, and alkyl groups.

Synthesis and biological evaluation of novel N-(5-phenyl-1H-pyrazol-3-yl)benzenesulfonamide derivatives as potential BRAFV600E inhibitors

A series of novel N-(5-phenyl-1H-pyrazol-3-yl)benzenesulfonamide derivatives (5a–5l) were synthesized and developed as potential BRAFV600E inhibitors. Among them, compound 5l exhibited the most potent inhibitory activity with an IC50

Synthesis, biological evaluation and 3D-QSAR studies of novel 5-phenyl-1 H -pyrazol cinnamamide derivatives as novel antitubulin agents

A series of novel 5-phenyl-1H-pyrazol derivatives (5a-5x) containing cinnamamide moiety were synthesized and their biological activities as potential tubulin polymerization inhibitors were evaluated. Among them, compound 5j exhibited the most potent inhibitory activity with an IC50 value of 1.02 μ1/4M for tubulin, which was superior to that of Colchicine (IC50 Combining double low line 1.34 μ1/4M). Docking simulation was performed to insert compound 5j into the crystal structure of tubulin at colchicine binding site to determine the probable binding model. 3D-QSAR model was also built to provide more pharmacophore understanding that could be used to design new agents with more potent tubulin inhibitory activity.

Design, synthesis, and evaluation of 2-aryl-7-(3′,4′-dialkoxyphenyl)-pyrazolo[1,5-a]pyrimidines as novel PDE-4 inhibitors

Described herein is design, synthesis, and biological evaluation of novel series of 2-aryl-7-(3′,4′-dialkoxyphenyl)-pyrazolo[1,5-a]pyrimidines acting as inhibitors of type 4 phosphodiesterase (PDE4) which is known as a good target for the treatment of asthma and COPD. For this purpose, structure optimization was conducted with the aid of structure-based drug design using the known X-ray crystallography. Also, biological effects of these compounds on the target enzyme were evaluated by using in vitro assays, leading to the potent and selective PDE-4 inhibitor (IC50 10 nM).

The Preparation of N-(1H-Pyrazol-3-yl)arylamides and 1H-Pyrazol-3-amines from Polylithiated C(α)N-Thiosemicarbazones and C(α),N-Semicarbazones

C(α),N-Tbiosemlcarbazones or C(α),N-semicarbazones were polylithiated with excess lithium diisopropylamide, and the resulting cyclized intermediates were condensed with aromatic esters to afford N-(1H-pyrazol-3-yl)arylamides. The polylithiated intermediates were also quenched with aqueous acid to give 5-substituted, 1H-pyrazol-3-amines.