208519-09-9

Basic information

• Product Name: 3-(3-CHLOROPHENYL)-1H-PYRAZOL-5-AMINE
• Synonyms: AA-0869;ZINC04234690;3-(3-CHLOROPHENYL)-1H-PYRAZOL-5-AMINE;5-(3-CHLORO-PHENYL)-2H-PYRAZOL-3-YLAMINE;3-Amino-5-(3-chlorophenyl)-1H-pyrazole;5-(3-Chlorophenyl)-1H-pyrazol-3-amine;5-AMino-3-(3-chlorophenyl)pyrazole;[5-(3-chlorophenyl)-1H-pyrazol-3-yl]amine
• CAS NO: 208519-09-9
• Molecular Formula: C₉H₈ClN₃
• Molecular Weight: 193.63
• Mol File: 208519-09-9.mol

Chemical Properties

• Melting Point: 138-140°C
• Boiling Point: 469.1°C at 760 mmHg
• Flash Point: 237.5°C
• Appearance: /
• Density: 1.378g/cm³
• Vapor Pressure: 5.69E-09mmHg at 25°C
• Refractive Index: 1.67
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-(3-CHLOROPHENYL)-1H-PYRAZOL-5-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3-CHLOROPHENYL)-1H-PYRAZOL-5-AMINE(208519-09-9)
• EPA Substance Registry System: 3-(3-CHLOROPHENYL)-1H-PYRAZOL-5-AMINE(208519-09-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 208519-09-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(3-CHLOROPHENYL)-1H-PYRAZOL-5-AMINE is used as a pharmaceutical agent for its antitumor properties, targeting various types of cancer by modulating oncological signaling pathways and exhibiting inhibitory effects on tumor growth and progression.
Additionally, it is used as an anti-inflammatory agent, leveraging its potential to reduce inflammation and alleviate symptoms associated with inflammatory conditions.
Used in Medicinal Chemistry Research:
3-(3-CHLOROPHENYL)-1H-PYRAZOL-5-AMINE serves as a key molecule in medicinal chemistry research, providing insights into the development of novel therapeutic agents with improved efficacy and selectivity for various diseases, including cancer and inflammatory disorders. Its unique chemical structure and properties make it an attractive candidate for further exploration and optimization in drug discovery processes.

InChI:InChI=1/C9H8ClN3/c10-7-3-1-2-6(4-7)8-5-9(11)13-12-8/h1-5H,(H3,11,12,13)

Upstream product

• 2905-65-9 methyl 3-chlorobenzoate 
• 21667-62-9 3-chlorobenzoylacetonitrile 

Downstream Products

• 203587-56-8 2-(3-Chloro-phenyl)-7-methyl-pyrazolo[1,5-a]pyrimidine-6-carboxylic acid ethyl ester 
• 77493-75-5 2-(3-chlorophenyl)-5-phenylpyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 1364597-43-2 methyl 2-(2-(3-chlorophenyl)-7-hydroxy-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate 
• 1232220-33-5 N-{2-(3-Chlorophenyl)-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidin-5-yl}-N'-(3-methyl-benzylidene)-hydrazine 
• 1232223-19-6 5-chloro-2-(3-chloro-phenyl)-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidine 
• 1159982-71-4 5,7-dichloro-2-(3-chlorophenyl)-pyrazolo[1,5-a]pyrimidine 
• 1245236-15-0 C₂₁H₁₆Cl₃N₃O₂ 

Relevant articles and documents

A new, one-pot, multicomponent synthesis of 5-aza-9-deaza-adenines under microwave irradiation

A new, practical, three-component method for the synthesis of 5-aza-9-deaza-adenines is developed. Aminopyrazoles react in a one-pot fashion with triethyl orthoformate and cyanamide under microwave irradiation affording 5-aza-9-deaza-adenines in good yiel

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.

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).

Novel potent neuropeptide Y Y5 receptor antagonists: Synthesis and structure-activity relationships of phenylpiperazine derivatives

A series of phenylpiperazine derivatives were synthesized and evaluated for their neuropeptide Y (NPY) Y5 receptor antagonistic activities. The benzindane portion of 2 was replaced by 1-phenylpiperazine, resulting in novel urea derivative 3f. Subsequent optimization of the phenylpiperazine template by substitution of the phenyl moiety resulted in a series of (2-methanesulfonamidephenyl)piperazine derivatives that showed potent binding affinity and antagonistic activity for the Y5 receptor.

Pyrazolo[1,5-a]pyrido[3,4-e]pyrimidin-6-ones. II. Synthesis and in vitro antimicrobial evaluation

A series of pyrazolo[1,5-a]pyrido[3,4-e]pyrimidin-6-ones (4a-p) was prepared by a simple synthetic procedure based on the reaction of hydroxylamine or methoxyamine with 2,3-substituted ethyl 7-dimethylaminovinyl pyrazolo[1,5-a]pyrimidin-6-carboxylates (3a