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4-Aminoantipyrine

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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
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Metabolites & Impurities
  • reagent
  • Drug bulk
  • Pyridines, Pyrimidines, Purines and Pteredines
  • Antibiotic Explorer
  • Pharmaceuticals
Mol File:
83-07-8.mol
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4-Aminoantipyrine Chemical Properties

Melting point:
105-110 °C(lit.)
Boiling point:
340 C
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
pka
pK1: 4.94(+1) (25°C)
form 
Powder or Crystals
color 
Yellow to yellow-brown
PH
7.1 (100g/l, H2O, 20℃)(slurry)
Odor
Odorless
Water Solubility 
ca. 500 g/L (20 ºC)
Merck 
14,591
BRN 
181635
Stability:
Stable. May be light sensitive.
LogP
-0.257 (est)
CAS DataBase Reference
83-07-8(CAS DataBase Reference)
NIST Chemistry Reference
Aminoantipyrene(83-07-8)
EPA Substance Registry System
4-Aminoantipyrene (83-07-8)
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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 
Yes
HS Code 
29331190
Toxicity
LD50 orally in Rabbit: 1700 mg/kg

MSDS

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4-Aminoantipyrine Usage And Synthesis

Chemical Properties

Amber crystalline powder

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.

Application

4-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.

Definition

ChEBI: 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.

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.

General Description

4-Aminoantipyrine forms heterocyclic Schiff bases, by reaction with various aldehydes and oximes. These Schiff bases form stable complexes with transition metals.

Purification Methods

It crystallises from EtOH or EtOH/ether. [Beilstein 25 III/IV 3554.]

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