57999-06-1

Basic information

• Product Name: 4-PHENYL-1H-PYRAZOL-5-AMINE
• Synonyms: BUTTPARK 49\07-31;AKOS B035600;AKOS BBS-00002654;4-PHENYL-2H-PYRAZOL-3-YLAMINE;4-PHENYL-1H-PYRAZOL-5-AMINE;1H-Pyrazol-5-amine, 4-phenyl-;4-phenyl-1H-pyrazol-5-ylamine
• CAS NO: 57999-06-1
• Molecular Formula: C₉H₉N₃
• Molecular Weight: 159.19
• Mol File: 57999-06-1.mol

Chemical Properties

• Melting Point: 175-177°C
• Boiling Point: 394.4°C at 760 mmHg
• Flash Point: 220.9°C
• Appearance: /
• Density: 1.238g/cm³
• Vapor Pressure: 1.99E-06mmHg at 25°C
• Refractive Index: 1.662
• CAS DataBase Reference: 4-PHENYL-1H-PYRAZOL-5-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PHENYL-1H-PYRAZOL-5-AMINE(57999-06-1)
• EPA Substance Registry System: 4-PHENYL-1H-PYRAZOL-5-AMINE(57999-06-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 57999-06-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-PHENYL-1H-PYRAZOL-5-AMINE is used as a building block for the synthesis of various organic compounds. Its unique structure allows for the creation of a wide range of chemical entities, making it a valuable component in the development of new molecules with specific properties.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 4-PHENYL-1H-PYRAZOL-5-AMINE is used as a precursor for the development of pharmaceuticals. Its potential pharmaceutical properties, such as anti-inflammatory and analgesic effects, make it a promising candidate for the treatment of various conditions.
Used in Corrosion Inhibition:
4-PHENYL-1H-PYRAZOL-5-AMINE has been investigated for its potential use as a corrosion inhibitor. Its ability to protect materials from corrosion makes it a valuable asset in industries where metal protection is crucial, such as in the automotive, aerospace, and construction sectors.
Used as a Precursor in the Synthesis of Biologically Active Compounds:
This chemical compound is also used as a precursor in the synthesis of various biologically active compounds. Its role in creating molecules with significant biological activity highlights its importance in the development of new drugs and therapeutic agents.

InChI:InChI=1/C9H9N3/c10-9-8(6-11-12-9)7-4-2-1-3-5-7/h1-6H,(H3,10,11,12)

Upstream product

• 51460-38-9 3-nitro-4-phenyl-1H-pyrazole 
• 70205-70-8 2-dimethylaminomethylene-2-phenylacetonitrile 
• 140-29-4 phenylacetonitrile 
• 613-90-1 benzoyl cyanide 
• 70205-70-8 α-phenyl β-dimethylaminoacrylonitrile 

Downstream Products

• 162286-98-8 ethyl 7-methyl-3-phenylpyrazolo<1,5-a>pyrimidine-6-carboxylate 
• 130506-84-2 6-acetyl-7-methyl-3-phenylpyrazolo<1,5-a>pyrimidine 
• 216661-54-0 3-(phenyl)-6-(4-methoxyphenyl)-pyrazolo(1,5-A)pyrimidine 
• 1207619-67-7 5,8,8-trimethyl-3-phenyl-6,7,8,9-tetrahydropyrazolo[1,5-a]quinazolin-6-one 
• 654635-42-4 9-trifluoromethyl-3-phenyl-5,6,7,8-tetrahydropyrazolo[5,1-b]quinazoline 
• 1207619-77-9 9-ethyl-6,6-dimethyl-3-phenyl-4,5,6,7,8,9-hexahydropyrazolo[5,1-b]quinazolin-8-one 
• 1235885-51-4 C₂₂H₁₅N₃ 
• 1358909-81-5 7-(naphtho[2,1-b]furan-2-yl)-3-phenylpyrazolo[1,5-a]pyrimidine 
• 1426834-63-0 5-phenyl-3-(3-phenylpyrazolo[1,5-a]pyrimidin-7-yl)-1-p-tolyl-1H-pyrazole-4-carbonitrile 
• 61552-61-2 5,7-dimethyl-3-phenylpyrazolo<1,5-a>pyrimidine 
• 767346-79-2 7-amino-3-phenyl-pyrazolo[1,5-a]pyrimidine-6-carbonitrile 
• 32016-25-4 7-amino-3,6-diphenylpyrazolo<1,5-a>pyrimidine 
• 1306738-72-6 3,8-diphenylpyrazolo[5,1-c][1,2,4]triazin-4-ylamine 
• 1455436-41-5 5-[3-nitro-4-(pyrrolidin-1-yl)phenyl]-3-phenyl-6,7,8,9-tetrahydropyrazolo[1,5-a]quinazoline 

Relevant articles and documents

COMPOUNDS AND MATRICES FOR USE IN BONE GROWTH AND REPAIR

Compositions of small molecules, matrices, and isolated cells including methods of preparation, and methods for differentiation, transdifferentiation, and proliferation of animal cells into the osteoblast blast cell lineage were described. Examples of ost

Discovery and characterization of a novel 7-aminopyrazolo[1,5-a]pyrimidine analog as a potent hepatitis C virus inhibitor

We describe a novel 7-aminopyrazolo[1,5-a]pyrimidine (7-APP) derivative as a potent hepatitis C virus (HCV) inhibitor. A series of 7-APPs was synthesized and evaluated for inhibitory activity against HCV in different cell culture systems. The synthesis and preliminary structure-activity relationship study of 7-APP are reported.

Study of regioselectivity of reactions between 3(5)-aminopyrazoles and 2-acetylcycloalkanones

Regioselectivity was examined of reactions between nine 3(5)-aminopyrazoles and 2-acetylcyclopentanone and 2-acetylcyclohexanone under various conditions. A series of cyclopenta[e]pyrazolo-[1,5-a]pyrimidines was obtained. The highest regioselectivity of the reaction was observed in alcohol at 20°C in the presence of a catalytic quantity of trifl uoroacetic acid. The regiostructure of compounds was established by 1H and 13C NMR spectroscopy. Pleiades Publishing, Ltd., 2012.

Microwave Mediated Facile Synthesis of Some Novel Pyrazole, Pyrazolo[1,5-a]pyrimidine and pyrazolo[5,1-c] [1,2,4]triazin derivatives

4-PHENYL-2H-pyrazol-3-ylamine 3 has been prepared by reaction of 2-phenyl-3-piperidine-1-yl-acrylonitrile(6) with hydrazine hydrate under microwave irradiation. Compound 3 reacted with acetylacetone and ethyl acetoacetate to yield pyrazolopyrimidine derivatives 7 and 8, respectively. Pyrazolopyrimidine derivative 11 can be formed by reaction of 3 with 2-ethoxymethylene-malononitrile. Compound 3 can be diazotised to yield the diazonium chloride and coupled with 6 to yield pyrazolotriazine derivative 25. Structures of the synthesized compounds were confirmed by their IR and NMR spectroscopic data.

Microwave-assisted protocols for the expedited synthesis of pyrazolo[1,5-a] and [3,4-d]pyrimidines

General, high-yielding MAOS protocols for the expedited synthesis of functionalized pyrazolo[1,5-a]pyrimidines and pyrazolo[3,4-b]pyrimidines, as well as their pyrazole precursors, are described amenable to an iterative analogue library synthesis strategy for lead optimization.

Structure-activity relationship study of bone morphogenetic protein (BMP) signaling inhibitors

A structure-activity relationship study of dorsomorphin, a previously identified inhibitor of SMAD 1/5/8 phosphorylation by bone morphogenetic protein (BMP) type 1 receptors ALK2, 3, and 6, revealed that increased inhibitory activity could be accomplished by replacing the pendent 4-pyridine ring with 4-quinoline. The activity contributions of various nitrogen atoms in the core pyrazolo[1,5-a]pyrimidine ring were also examined by preparing and evaluating pyrrolo[1,2-a]pyrimidine and pyrazolo[1,5-a]pyridine derivatives. In addition, increased mouse liver microsome stability was achieved by replacing the ether substituent on the pendent phenyl ring with piperazine. Finally, an optimized compound 13 (LDN-193189 or DM-3189) demonstrated moderate pharmacokinetic characteristics (e.g., plasma t1/2 = 1.6 h) following intraperitoneal administration in mice. These studies provide useful molecular probes for examining the in vivo pharmacology of BMP signaling inhibition.

Synthesis and initial SAR studies of 3,6-disubstituted pyrazolo[1,5-a]pyrimidines: A new class of KDR kinase inhibitors

We have synthesized and evaluated the activity of 3,6-disubstituted pyrazolo[1,5-a]pyrimidines as a new class of KDR kinase inhibitors. Starting with screening lead 1, potency against isolated KDR was fully optimized with 3-thienyl and 4-methoxyphenyl substituents at the 6- and 3-positions (3g, KDR IC50=19 nM), respectively. The synthesis and SAR of these compounds are described.