4-Aminoantipyrine Property

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)

Safety

Hazard Codes 

Xn

Risk Statements 

22-36/37/38-20/21/22

Safety Statements 

26-36-36/37/39

WGK Germany 

3

RTECS 

CD2480000

F 

8-9-23

Hazard Note 

Harmful

TSCA 

Yes

HS Code 

29331190

Toxicity

LD50 orally in Rabbit: 1700 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

4-Aminoantipyrine Chemical Properties,Usage,Production

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.]