4-Aminoantipyrine
4-AAP · AMPYRONE · AMINOANTIPYRINE · 4-AMINOPHENAZONE · 4-AMINOANTIPYRIN · 4-Amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one · 4-AMINOANTIPYRENE · 4-AMINO-2,3-DIMETHYL-1-PHENYL-3-PYRAZOLIN-5-ONE
Identifiers & Physical Properties
| CAS No. | 83-07-8 |
|---|---|
| Molecular formula | C11H13N3O |
| Average molar mass | 203.24 g/mol |
| Monoisotopic mass | 203.10586204 g/mol |
| SMILES | Cc1c(N)c(=O)n(-c2ccccc2)n1C |
| InChIKey | RLFWWDJHLFCNIJ-UHFFFAOYSA-N |
| PubChem CID | 2151 |
| ChEMBL | CHEMBL1165011 |
| ChEBI | CHEBI:59026 |
| EC No. | 201-452-3 |
| DTXSID | DTXSID8048860 |
Chemical & Physical Properties
| XLogP | 0.1 |
|---|---|
| Topological polar surface area | 49.6 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 1 |
| Heavy atoms | 15 |
| Formal charge | 0 |
| Complexity | 305 |
| Drugs | Pharmaceuticals -> Metabolite of Metamizole |
| Animal Drugs | Pharmaceuticals -> Animal Drugs -> Approved in Taiwan |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Collision Cross Section | 151.49 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]142.6 Ų [M+H]+ [CCS Type: TW142.48 Ų [M+H]+ |
| Melting point | 105-110 °C(lit.) |
| Boiling point | 340 C |
| Density | 0.8 |
| Bulk density | 430kg/m3 |
| Refractive index | 1.4930 (estimate) |
| Storage conditions | Keep in dark place,Inert atmosphere,Room temperature |
| Solubility | H2O: 0.1 g/mL, clearca. 500 g/L (20 ºC) |
| pKa (acidity coefficient) | pK1: 4.94(+1) (25°C) |
| Physical state | Powder or Crystals |
| Color | Yellow to yellow-brown |
| pH | 7.1 (100g/l, H2O, 20℃)(slurry) |
| Odor | Odorless |
| Merck | 14,591 |
| BRN | 181635 |
| Stability | Stable. May be light sensitive. |
| InChI | 1S/C11H13N3O/c1-8-10(12)11(15)14(13(8)2)9-6-4-3-5-7-9/h3-7H,12H2,1-2H3 |
| InChIKey | RLFWWDJHLFCNIJ-UHFFFAOYSA-N |
| SMILES | CN1N(c2ccccc2)C(=O)C(N)=C1C |
| LogP (partition coefficient) | -0.257 (est) |
| CAS DataBase Reference | 83-07-8(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | 0M0B7474RA |
| NIST Chemistry Reference | Aminoantipyrene(83-07-8) |
| EPA Substance Registry System | 4-Aminoantipyrene (83-07-8) |
| UNSPSC Code | 51384603 |
| NACRES | NA.31 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302 |
| GHS precautionary statements | P264-P270-P301+P312-P501 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xn |
| Risk statements (R) | 22-36/37/38-20/21/22 |
| Safety statements (S) | 26-36-36/37/39 |
| Water hazard class (WGK) | 3 |
| RTECS number | CD2480000 |
| F | 8-9-23 |
| Hazard Note | Harmful |
| TSCA inventory status | TSCA listed |
| Customs code | 29331190 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Acute Tox. 4 Oral |
| Toxicity | LD50 orally in Rabbit: 1700 mg/kg |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 1% (1 of 105) of reports.WarningH302 (99%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 105 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | 4-Amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | IMAP assessments - 3H-Pyrazol-3-one, 4-amino-1,2-dihydro-1,5-dimethyl-2-phenyl-: Environment tier I assessment |
| Hazard Classes and Categories | Acute Tox. 4 (99%) |
| F | 8-9-23 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | CD2480000 |
| Customs code | 29331190 |
| Toxicity | LD50 orally in Rabbit: 1700 mg/kg |
| Risk statements (R) | 22-36/37/38-20/21/22 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xn |
| hazard_note | Harmful |
| Safety statements (S) | 26-36-36/37/39 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H302 |
| Hazard class | Acute Tox. 4 Oral |
| GHS precautionary statements | P264-P270-P301+P312-P501 |
Applications & Uses
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.
General Description
4-Aminoantipyrine forms heterocyclic Schiff bases, by reaction with various aldehydes and oximes. These Schiff bases form stable complexes with transition metals.
Preparation & Synthesis
Preparation
synthesis of 4-aminoantipyrine: Antipyrine is nitrosated by sodium nitrite, reduced by ammonium bisulfite and ammonium sulfite, hydrolyzed by sulfuric acid, and finally neutralized with liquid ammonia to obtain 4-aminoantipyrine.