41596-67-2

Basic information

• Product Name: 1,2(4)-topaminequinone
• Synonyms: 1,2(4)-topaminequinone
• CAS NO: 41596-67-2
• Molecular Formula: C8H9NO3
• Molecular Weight: 167.16196
• Mol File: 41596-67-2.mol

Chemical Properties

• Boiling Point: 302.5°Cat760mmHg
• Flash Point: 136.7°C
• Appearance: /
• Density: 1.39g/cm³
• Vapor Pressure: 9.56E-05mmHg at 25°C
• Refractive Index: 1.607
• CAS DataBase Reference: 1,2(4)-topaminequinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2(4)-topaminequinone(41596-67-2)
• EPA Substance Registry System: 1,2(4)-topaminequinone(41596-67-2)

Safety Data

• Hazardous Substances Data: 41596-67-2(Hazardous Substances Data)

Usage

Chemical class

Quinones

Origin

Derived from the oxidation of 1,2-diamines

Physical state

Yellow crystalline solid

Solubility

Soluble in organic solvents

Odor

Characteristic odor

Uses

Precursor for the synthesis of various organic compounds

Applications

Pharmaceutical, dye, and polymer industries

Potential properties

Antioxidant and antibacterial

Field of interest

Medicinal chemistry

Safety precautions

Corrosive and toxic if inhaled, ingested, or absorbed through the skin

InChI:InChI=1/C8H9NO3/c9-2-1-5-3-7(11)8(12)4-6(5)10/h3-4,10H,1-2,9H2

Upstream product

• 1199-18-4 6-Hydroxydopamin 

Relevant articles and documents

The oxidation of 6-hydroxydopamine in aqueous solution. Part 3. Kinetics and mechanism of the oxidation with iron(III)

The kinetics of the oxidation of 6-hydroxydopamine [5-(2-aminoethyl)benzene-1,2,4-triol, protonated form H3LH+] by iron(III) under anaerobic conditions are presented. A complex mechanism whereby the o- (oQ), p- (pQ), and triketoquinones (tQ) are formed via parallel inner- and outer-sphere electron transfer mechanisms has been established. The outer-sphere mechanism is particularly fast (nearly diffusion limiting) and predominates. By following the dependence of the rate on ionic strength it has been shown that a deprotonated form of 6-hydroxydopamine reacts via an outer-sphere reaction with all species of iron. Like the other catecholamines [3,4-dihydroxy-1-(2-amino-ethyl)benzenes], but to a much smaller extent, complex formation occurs by FeOH2+ reacting with the fully protonated form of 6-hydroxydopamine. Three different semiquinones are initially produced; two of them, the triketo- and p-semiquinones, are tautomers. The o- and triketo-semiquinones react quickly with another iron atom to form their respective quinones. The p-semiquinone, however, is seemingly stable, partly reacting with more iron and partly disproportionating to form pQ and reforming 6-hydroxydopamine. At pHs above 2.5. pQ and oQ are in equilibrium via a deprotonated quinone Q-. The biological implications of this mechanism are discussed.

The oxidation of 6-hydroxydopamine in aqueous solution. Part 1. The formation of three metastable quinones at low pH

1H and 13C NMR investigations have been carried out in order to elucidate the products of oxidation of 6-hydroxy-dopamine [5-(2-aminoethyl)benzene-1,2,4-triol, protonated form H3LH+]. Stopped-flow, NMR kinetic experiments, and quantum mechanical calculations were employed as additional aids to the interpretation of the results. Evidence is provided that, at low pH, three quinones are produced that are in metastable equilibrium, namely the p- (pQ), o- (oQ), and triketo-quinones (tQ). Results obtained with sodium periodate and iron(III) are compared and discussed. At higher pHs (>2.5) the quinones reach rapid equilibrium because they start to deprotonate, all giving rise to the same species (Q-), which is the only species detectable above a pH of about 6 and which is stable over a large pH range.