7152-40-1

Basic information

• Product Name: 5-AMINO-4-CYANO-3-CYANOMETHYL-1-PHENYLPYRAZOLE
• Synonyms: 5-AMINO-4-CYANO-3-CYANOMETHYL-1-PHENYLPYRAZOLE;5-AMINO-4-CYANO-1-PHENYL-3-PYRAZOLEACETONITRILE;5-AMINO-3-(CYANOMETHYL)-1-PHENYL-1H-PYRAZOLE-4-CARBONITRILE;AKOS BBS-00000168;AKOS B029199;TIMTEC-BB SBB003332;1-phenyl-3-cyanomethyl-4-cyano-5-aminopyrazole;5-amino-3-cyanomethyl-1-phenyl-4-pyrazolecarbonitril
• CAS NO: 7152-40-1
• Molecular Formula: C₁₂H₉N₅
• Molecular Weight: 223.23
• EINECS: 230-496-6
• Product Categories: Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines
• Mol File: 7152-40-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 164-165°C
• Boiling Point: 354.52°C (rough estimate)
• Flash Point: 248.2 °C
• Appearance: /
• Density: 1.2950 (rough estimate)
• Vapor Pressure: 1.26E-09mmHg at 25°C
• Refractive Index: 1.6610 (estimate)
• PKA: -1?+-.0.10(Predicted)
• BRN: 217441
• CAS DataBase Reference: 5-AMINO-4-CYANO-3-CYANOMETHYL-1-PHENYLPYRAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-4-CYANO-3-CYANOMETHYL-1-PHENYLPYRAZOLE(7152-40-1)
• EPA Substance Registry System: 5-AMINO-4-CYANO-3-CYANOMETHYL-1-PHENYLPYRAZOLE(7152-40-1)

Safety Data

• Hazard Codes: T
• Statements: 22-23/24/25
• Safety Statements: 22-36/37-45-36/37/39-28-27
• RIDADR: 3276
• RTECS: UQ6260000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 7152-40-1(Hazardous Substances Data)

Usage

General Description

5-Amino-4-cyano-3-cyanomethyl-1-phenylpyrazole is a chemical compound with the molecular formula C11H7N5. It is a pyrazole derivative with a phenyl group and multiple cyano and amino functional groups attached to the pyrazole ring. 5-AMINO-4-CYANO-3-CYANOMETHYL-1-PHENYLPYRAZOLE has potential applications in the field of organic synthesis and pharmaceutical research. Its unique structure and properties make it a valuable building block for the synthesis of various heterocyclic compounds and potential drug candidates. Its precise uses and properties may vary depending on the specific application and the synthesis process involved.

InChI:InChI=1/C12H9N5/c13-7-6-11-10(8-14)12(15)17(16-11)9-4-2-1-3-5-9/h1-5H,6,15H2

Upstream product

• 100-63-0 phenylhydrazine 
• 109-77-3 malononitrile 
• 64-17-5 ethanol 
• 868-54-2 1,1,3-tricyano-2-amino-1-propene 

Downstream Products

• 475093-69-7 N-(4,6-dioxo-2-phenyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]-pyridine-3-yl)acetamide 
• 99844-21-0 2-(5-amino-1-phenyl-1H-pyrazol-3-yl)acetic acid 
• 746604-52-4 5-amino-3-[1-cyano-2-(2,6-dimethoxyphenyl)vinyl]-1-phenyl-1H-pyrazole-4-carbonitrile 
• 475094-41-8 C₁₂H₇BrN₄ 
• 475091-93-1 C₁₂H₉N₃O₂ 
• 475094-40-7 C₁₂H₈N₄ 
• 475094-47-4 C₁₄H₁₁N₅ 
• 103096-39-5 (4-cyano-5-cyanomethyl-2-phenyl-2H-pyrazol-3-yl)-oxalomonoimidic acid-2-ethyl ester-1-methyl ester 
• 101352-58-3 4-amino-3-cyanomethyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine-6-carboxylic acid ethyl ester 
• 100137-09-5 (5-amino-4-cyano-1-phenyl-1H-pyrazol-3-yl)-acetic acid 
• 108564-92-7 3-amino-2-phenyl-2H-pyrazolo[4,3-c]pyridine-4,6(5H,7H)-dione 

Relevant articles and documents

Isoquinoline-1,3-diones as Selective Inhibitors of Tyrosyl DNA Phosphodiesterase II (TDP2)

Tyrosyl DNA phosphodiesterase II (TDP2) is a recently discovered enzyme that specifically repairs DNA damages induced by topoisomerase II (Top2) poisons and causes resistance to these drugs. Inhibiting TDP2 is expected to enhance the efficacy of clinically important Top2-targeting anticancer drugs. However, TDP2 as a therapeutic target remains poorly understood. We report herein the discovery of isoquinoline-1,3-dione as a viable chemotype for selectively inhibiting TDP2. The initial hit compound 43 was identified by screening our in-house collection of synthetic compounds. Further structure-activity relationship (SAR) studies identified numerous analogues inhibiting TDP2 in low micromolar range without appreciable inhibition against the homologous TDP1 at the highest testing concentration (111 μM). The best compound 64 inhibited recombinant TDP2 with an IC50 of 1.9 μM. The discovery of this chemotype may provide a platform toward understanding TDP2 as a drug target.

Divergent cyclisations of 2-(5-amino-4-carbamoyl-1H-pyrazol-3-yl)acetic acids with formyl and acetyl electrophiles

The reaction of 2-(5-amino-4-carbamoyl-1-methyl-1H-pyrazol-3-yl)acetic acid and triethylorthoformate did not give the expected dihydropyrazolo[4,3-c]pyridin-4-one product as described in literature, but formed an alternative cyclic imide product, fully characterised by NMR and X-ray crystallography. This mode of reaction was shown to be general to other 1-substituted-2-(5-amino-4-carbamoyl-1H-pyrazol-3-yl)acetic acids. The outcome of the cyclisation was highly sensitive both to the nature of the reagents used and also to the acidity of the reaction medium, such that a number of interesting bicyclic heterocycles could be produced in a controlled fashion from the single starting material. The major tautomeric forms of the bicyclic products in solution were found to vary according to their substitution pattern.