3-Amino-5-phenylpyrazole

Base Information

• Chemical Name: 3-Amino-5-phenylpyrazole
• CAS No.: 1572-10-7
• Molecular Formula: C9H9N3
• Molecular Weight: 159.191
• Hs Code.: 29331990
• European Community (EC) Number: 626-099-6,673-954-4
• DSSTox Substance ID: DTXSID80935629
• Nikkaji Number: J593.495H,J884.051B
• Wikidata: Q72440879
• ChEMBL ID: CHEMBL1650269
• Mol file: 1572-10-7.mol

Synonyms:Pyrazole,3(or 5)-amino-5(or 3)-phenyl- (7CI);Pyrazole, 3-amino-5-phenyl- (8CI);3-Amino-5-phenyl-1H-pyrazole;3-Amino-5-phenyl-2H-pyrazole;3-Phenyl-1H-pyrazol-5-amine;3-Phenyl-5-aminopyrazole;3-Phenyl-5-pyrazolamine;5-Phenyl-1-pyrazol-3-amine;5-Phenyl-1H-pyrazol-3-amine;5-Phenyl-1H-pyrazol-3-ylamine;5-Phenyl-3-aminopyrazole;5-Phenyl-3-pyrazolamine;

Chemical Property of 3-Amino-5-phenylpyrazole

Chemical Property:

• Appearance/Colour: Off-white to cream colored crystalline powder
• Vapor Pressure: 5.1E-08mmHg at 25°C
• Melting Point: 124-127 °C(lit.)
• Refractive Index: 1.662
• Boiling Point: 442.3ºC at 760 mmHg
• PKA: 14.80±0.10(Predicted)
• Flash Point: 251.5ºC
• PSA: 54.70000
• Density: 1.238g/cm3
• LogP: 2.24010
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: DMSO, Methanol
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 159.079647300
• Heavy Atom Count: 12
• Complexity: 143

Purity/Quality:

97% ^*data from raw suppliers

3-Amino-5-phenylpyrazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC(=NN2)N
• Recent EU Clinical Trials: Nitroglycerin's effect on perfusion and hypoxia in human non small cell lung cancer: proof of principle, a phase II trial
• General Description: 3-Amino-5-phenylpyrazole serves as a key scaffold in the design of small-molecule mercaptoacetamide analogs targeting botulinum neurotoxin serotype A (BoNT/A). The scaffold's structural features, particularly when combined with electron-withdrawing substituents on the phenyl ring (e.g., chloro or trifluoromethyl groups), enhance inhibitory potency against BoNT/A's metalloprotease activity. These analogs demonstrate low micromolar activity and improved cellular efficacy, positioning them as promising candidates for therapeutic development against botulinum intoxication. (Note: The paragraph synthesizes the role of 3-amino-5-phenylpyrazole in the context of the study's findings without describing the literature itself.)

Technology Process of 3-Amino-5-phenylpyrazole

There total 22 articles about 3-Amino-5-phenylpyrazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

erythro-2,3-dibromo-3-phenylpropanenitrile (19521-13-2,85485-68-3,98361-10-5) → 3(5)-phenylpyrazol-5(3)-amine (1572-10-7)

Guidance literature:

With potassium carbonate; hydrazine hydrate; In methanol; water; r.t. 5 h, then 50-60 deg C 24 h;

Reference yield: 86.0%

4-bromo-3-chloro-5-phenylisothiazole (19993-34-1) → 4-bromo-3-hydrazinyl-5-phenylisothiazole (1187734-02-6) + 3(5)-phenylpyrazol-5(3)-amine (1572-10-7)

Guidance literature:

With hydrazine; at 200 ℃; for 0.05h;

DOI:10.1016/j.tet.2009.06.041

Reference yield: 81.0%

3-amino-4-bromo-5-phenylisothiazole (90792-75-9) → 3(5)-phenylpyrazol-5(3)-amine (1572-10-7)

Guidance literature:

With hydrazine; at 110 ℃; for 120h;

DOI:10.1016/j.tet.2009.06.041

upstream raw materials:

acetophenone semicarbazone

ethylmagnesium bromide

2-benzoyl-3-phenylacrylonitrile

3-amino-3-phenylacrylonitrile

Downstream raw materials:

6-methyl-7-oxo-2-phenyl-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-5-carboxylic acid ethyl ester

N-(5-phenyl-1H-pyrazol-3-yl)acetamide

5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-7(4H)-one

2,5-diphenylpyrazolo[1,5-a]pyrimidin-7(4H)-one

Refernces

Botulinum neurotoxin serotype A inhibitors: Small-molecule mercaptoacetamide analogs

10.1016/j.bmc.2009.03.013

This research aims to develop small-molecule inhibitors against botulinum neurotoxin serotype A (BoNT/A), a highly toxic substance that causes botulism and poses a significant threat due to its potential use in bioterrorism. The study focuses on designing mercaptoacetamide analogs that can inhibit the zinc-dependent metalloprotease activity of BoNT/A, which is responsible for cleaving proteins involved in neurotransmitter release, leading to paralysis. The researchers synthesized a series of 2-mercaptoacetamide analogs based on a 5-amino-3-phenylpyrazole scaffold and investigated their structure–activity relationships. Key findings include the critical role of the sulfur atom in the mercaptoacetamide for inhibitory activity and the influence of substituents on the phenyl ring, with electron-withdrawing groups like chlorine and trifluoromethyl showing enhanced potency. The most active analogs, such as 12a (4-chloro) and 12d (4-trifluoromethyl), demonstrated low micromolar inhibitory activity against BoNT/A. These mercaptoacetamide inhibitors not only showed equipotency with previously reported hydroxamic acid inhibitors but also exhibited better cellular activity, suggesting they could prevent SNARE cleavage in neuronal cells without pre-incubation with the toxin. The study concludes that these novel mercaptoacetamide-based inhibitors are promising lead structures for further development into therapeutic agents against botulinum intoxication.