95750-98-4

Basic information

• Product Name: 4-(2-chlorophenyl)-1H-pyrazol-5-amine
• Synonyms: 4-(2-chlorophenyl)-1H-pyrazol-5-amine;4-(2-Chlorophenyl)-1H-pyrazol-3-aMine;4-(2-chloro-phenyl)-2h-pyrazol-3-ylaMine;4-(2-Chlorophenyl)-1H-pyrazole-3-amine;4-(2-chloro-phenyl)-1(2)H-pyrazol-3-ylamine
• CAS NO: 95750-98-4
• Molecular Formula: C₉H₈ClN₃
• Molecular Weight: 193.63292
• Mol File: 95750-98-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(2-chlorophenyl)-1H-pyrazol-5-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-chlorophenyl)-1H-pyrazol-5-amine(95750-98-4)
• EPA Substance Registry System: 4-(2-chlorophenyl)-1H-pyrazol-5-amine(95750-98-4)

Safety Data

• Hazardous Substances Data: 95750-98-4(Hazardous Substances Data)

Usage

Structure

Pyrazole derivative with a substituted chlorophenyl group attached to the fourth carbon and an amino group attached to the fifth carbon of the pyrazole ring.

Applications

Medicinal Chemistry: Potential applications in the development of pharmaceutical drugs.
Building Block: Used in the synthesis of various bioactive compounds with potential therapeutic properties.
Research Tool: Utilized in the study of biochemical pathways.
Drug Development: Starting material for the development of new drugs targeting specific biological pathways.

Safety Precautions

Proper handling, storage, and disposal procedures should be followed to ensure safety.

Upstream product

• 75175-24-5 α-formyl-2-chlorobenzeneacetonitrile 
• 2856-63-5 2-Chlorophenylacetonitrile 

Downstream Products

• 1264295-07-9 C₂₄H₂₂ClN₃O₂ 

Relevant articles and documents

Synthesis and biological evaluation of novel pyrazolo[1,5-a]pyrimidines: Discovery of a selective inhibitor of JAK1 JH2 pseudokinase and VPS34

A series of novel 3,6-di-substituted or 3-substituted pyrazolo[1,5-a]pyrimidines were prepared via a microwave-assisted approach that generated a broad array of derivatives in good yields (20–93%, ave. = 59%). The straightforward synthesis involved sequential treatment of commercially-available acetonitrile derivatives with DMF-dimethylacetal (120 °C, 20 min), followed by treatment with NH2NH2·HBr (120 °C, 20 min), and 1,1,3,3-tetramethoxypropane or 2-aryl-substituted malondialdehdyes (120 °C, 20 min). Compounds were screened for antimitotic activities against MCF7 breast cancer and/or A2780 ovarian cancer cell lines in vitro. The most active compounds exhibited EC50 values ranging from 0.5 to 4.3 μM, with the 3-(4-(trifluoromethyl)phenyl)-6-[4-(2-(piperidin-1-yl)ethoxy]phenyl analogue (34e) and the 3-(2-fluorophenyl)-6-[4-(2-(4-methylpiperizin-1-yl)ethoxy]phenyl analogue (35a) being two to three fold more active than Compound C (Dorsomorphin) in A2780 and MCF7 assays, respectively. Importantly, a monosubstituted 3-(benzothiazol-2-yl) derivative (13) was equipotent with the more synthetically challenging 3,6-disubstituted derivatives (34a–e and 35a–e), and exhibited a promising and unique selectivity profile when screened against a panel consisting of 403 protein kinases (Kinomescan selectivity score = 0.005, Kd = 0.55 ± 0.055 μM and 0.410 ± 0.20 μM for JAK1 JH2 pseudokinase and VPS34, respectively).

New 2,3-substituted 4,7-dihydro-6-(1'H-pyrazol-3'-yl)pyrazolo[1,5-a]pyrimidin-7-ones and related compounds: Synthesis and benzodiazepine receptor binding study

The reaction between two series of 7-dimethylaminovinyl pyrazolo[1,5-a]pyrimidines 4(a-r) 7a, 7d, 7f, 7(h-j) and hydrazine in acetic acid is investigated. The structure of 4,7-dihydro-6-(1'H-pyrazol-3'-yl)pyrazolo[1,5-a]pyrimidin-7-ones 5(a-r) and 7-methyl-6-(1'H-pyrazol-3'-yl)pyrazolo[1,5a]pyrimidines 8a, 8d, 8f, 8(h-j) are attributed to the isolated products and the pathway of this reaction is suggested. The in vitro benzodiazepine receptor (BzR) affinity of the title compounds are determined by testing their ability to displace 3H-flunitrazepam from its specific binding in bovine brain membranes. The IC50 and GABA (γ-aminobutyric acid) ratio values give valuable indications about affinity and behavioural profile of these new BzR ligands. Included in this investigation are indicated several structure affinity relationships of the title compounds.