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4-Aminoantipyrine

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CAS:83-07-8
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4-Aminoantipyrine Basic information
Product Name:4-Aminoantipyrine
Synonyms:Metamizole EP Impurity B;4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one;Metamizole Sodium Impurity 2(Minocycline EP Impurity B);4-aminoantipirine;4-Amine-2,3-dimethyl-lphenyl-5-pyrazolone-[5],Ampyrone;4-amino-1,2-dihydro-1,5-dimethyl-2-phenyl-3h-pyrazol-3-on;AKOS BBS-00007964;AMINOANTIPYRINE
CAS:83-07-8
MF:C11H13N3O
MW:203.24
EINECS:201-452-3
Product Categories:PYRAMIDON;Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals;reagent;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Drug bulk;Antibiotic Explorer;Pyridines, Pyrimidines, Purines and Pteredines
Mol File:83-07-8.mol
4-Aminoantipyrine Structure
4-Aminoantipyrine Chemical Properties
Melting point 105-110 °C(lit.)
Boiling point 340 C
bulk density430kg/m3
density 0.8
refractive index 1.4930 (estimate)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility H2O: 0.1 g/mL, clear
pkapK1: 4.94(+1) (25°C)
form Powder or Crystals
color Yellow to yellow-brown
OdorOdorless
PH7.1 (100g/l, H2O, 20℃)(slurry)
Water Solubility ca. 500 g/L (20 ºC)
Merck 14,591
BRN 181635
Stability:Stable. May be light sensitive.
InChI1S/C11H13N3O/c1-8-10(12)11(15)14(13(8)2)9-6-4-3-5-7-9/h3-7H,12H2,1-2H3
InChIKeyRLFWWDJHLFCNIJ-UHFFFAOYSA-N
SMILESCN1N(c2ccccc2)C(=O)C(N)=C1C
LogP-0.257 (est)
CAS DataBase Reference83-07-8(CAS DataBase Reference)
NIST Chemistry ReferenceAminoantipyrene(83-07-8)
EPA Substance Registry System4-Aminoantipyrene (83-07-8)
Safety Information
Hazard Codes Xn
Risk Statements 22-36/37/38-20/21/22
Safety Statements 26-36-36/37/39
WGK Germany 3
RTECS CD2480000
8-9-23
Hazard Note Harmful
TSCA TSCA listed
HS Code 29331190
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
ToxicityLD50 orally in Rabbit: 1700 mg/kg
MSDS Information
ProviderLanguage
Ampyrone English
SigmaAldrich English
ACROS English
ALFA English
4-Aminoantipyrine Usage And Synthesis
Chemical PropertiesIt is an amber to pale yellow crystalline powder. It is soluble in water, benzene, and ethanol, and only slightly soluble in diethyl ether.
Uses4-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.
Application4-aminoantipyrine is the most widely used analytical reagent for the estimation of phenol. It is used as a reagent for glucose determination in the presence of peroxidase and phenol. It is also used as indicator for trace phenol determinations in water.
Phenolic compounds were determined by buffering the sample to a pH of 10.0 and adding 4-aminoantipyrine to produce a yellow or amber colored complex in the presence of ferricyanide ion. The colour is intensified through extraction of the complex into chloroform. Measurement of this colour quantitatively determines the phenol concentration of the sample.
DefinitionChEBI: 4-aminoantipyrine is a pyrazolone, a member of the class of pyrazoles that is antipyrine substituted at C-4 by an amino group. It is a metabolite of aminopyrine and of metamizole. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antirheumatic drug, a peripheral nervous system drug, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, an antipyretic, a drug metabolite and a marine xenobiotic metabolite. It is a primary amino compound and a pyrazolone. It derives from an antipyrine.
Preparationsynthesis 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.
General Description4-Aminoantipyrine forms heterocyclic Schiff bases, by reaction with various aldehydes and oximes. These Schiff bases form stable complexes with transition metals.
Purification MethodsIt crystallises from EtOH or EtOH/ether. [Beilstein 25 III/IV 3554.]
Tag:4-Aminoantipyrine(83-07-8) Related Product Information
Cefazolin sodium salt Cefazolin Chlorodimethylphenylsilane Dimethyl ether Dimethyl fumarate Dimethyl carbonate N,N-Dimethyl-1,4-phenylenediamine Antipyrine Dimethyl sebacate Glucosamine Propyphenazone 4,4'-Diaminodiphenylsulfone N,N-Dimethylformamide Acetaminophen 3,4'-DIAMINODIPHENYLMETHANE Dimethyl sulfoxide DIANTIPYRYLMETHANE EC 2.6.1.2

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