4-Aminoantipyrine

Base Information

• Chemical Name: 4-Aminoantipyrine
• CAS No.: 83-07-8
• Molecular Formula: C11H13N3O
• Molecular Weight: 203.244
• Hs Code.: 29331190
• European Community (EC) Number: 201-452-3
• NSC Number: 60242
• UNII: 0M0B7474RA
• DSSTox Substance ID: DTXSID8048860
• Nikkaji Number: J796J
• Wikipedia: Ampyrone
• Wikidata: Q3599043
• Metabolomics Workbench ID: 60356
• ChEMBL ID: CHEMBL1165011
• Mol file: 83-07-8.mol

Synonyms:4 Amino 1,5 Dimethyl 2 Phenyl 3H Pyrazolone;4 Aminoantipyrine;4 Aminophenazone;4-Amino-1,5-Dimethyl-2-Phenyl-3H-Pyrazolone;4-Aminoantipyrine;4-Aminophenazone;Aminoantipyrine;Ampyrone

Chemical Property of 4-Aminoantipyrine

Chemical Property:

• Appearance/Colour: Amber crystalline powder
• Vapor Pressure: 0.000659mmHg at 25°C
• Melting Point: 105-110 °C(lit.)
• Refractive Index: 1.606
• Boiling Point: 309 °C at 760 mmHg
• PKA: pK1: 4.94(+1) (25°C)
• Flash Point: 140.7 °C
• PSA: 52.95000
• Density: 1.207 g/cm³
• LogP: 1.64780
• Storage Temp.: Store at RT.
• Solubility.: H2O: 0.1 g/mL, clear
• Water Solubility.: ca. 500 g/L (20 ºC)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 203.105862047
• Heavy Atom Count: 15
• Complexity: 305

Purity/Quality:

99%, ^*data from raw suppliers

4-Aminophenazone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)N(N1C)C2=CC=CC=C2)N
• Uses: 4-Aminoantipyrine is a metabolite of aminopyrine, having both analgesic and anti-inflammatory properties. It readily forms metal complexes due to its amino nitrogen, a strong coordination site.4-aminoantipyrine forms Schiff bases when treated with aldehydes/ketones, which are used in chemosensing applications.Coupling Reagent for Trinder's reagent in colorimetric hydrogen peroxide detectionassays.Forms highly stable dyes by coupling with Trinder's reagent in presence of Peroxidase and H2O2. Therefore suitable for use in test strip and solution diagnostics.

Technology Process of 4-Aminoantipyrine

There total 31 articles about 4-Aminoantipyrine 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: 98.0%

4-[N-[(1,1-dimethylethoxy)carbonyl]amino]-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one → 4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one (83-07-8)

Guidance literature:

With sulfuric acid; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1016/j.tetlet.2005.01.129

Reference yield: 80.0%

1,5-dimethyl-4-nitroso-2-phenyl-1,2-dihydro-pyrazol-3-one (885-11-0) → 4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one (83-07-8)

Guidance literature:

With ammonium hydroxide; hydrogen sulfide; In water; for 0.25h; Heating;

Reference yield: 67.0%

1,5-dimethyl-4-nitro-2-phenyl-1H-pyrazole-3(2H)-one (30672-29-8) → 4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one (83-07-8)

Guidance literature:

With hydrazine hydrate; In ethanol; for 24h; chemoselective reaction; Irradiation;

DOI:10.1039/c8nj05260c

upstream raw materials:

1,5-dimethyl-4-nitroso-2-phenyl-1,2-dihydro-pyrazol-3-one

aminopyrine

N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pryazol-4-yl)benzamide

metamizol

Downstream raw materials:

1,5,5'-trimethyl-2,2'-diphenyl-1,2,2',4'-tetrahydro-4,4'-azanylylidene-bis-pyrazol-3-one

4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino)-3-phenyl-4H-isoxazol-5-one

2-cyano-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide

1,5-dimethyl-2-phenyl-4-(2-thioxo-5,6-dihydro-2H-[1,3]thiazin-4-ylamino)-1,2-dihydro-pyrazol-3-one

Refernces

• 1、 Tok, Fatih,Ko?yi?it-Kaymak??o?lu, Bedia,Sa?l?k, Begüm Nurpelin,Levent, Serkan,?zkay, Yusuf,Kaplanc?kl?, Zafer As?m. "Synthesis and biological evaluation of new pyrazolone Schiff bases as monoamine oxidase and cholinesterase inhibitors". . p. 41 - 50. Retrieved 2018/11/27.
• 2、 -. "Synthetic process of 4-ampyrone product". Paragraph 0011-0015. . Retrieved 2017/07/12.