29539-03-5

Basic information

• Product Name: 5,6-DIHYDROXYINDOLINE HBR
• Synonyms: DIHYDROXYINDOLINE;5,6-Dihydroxyindoline hydrobromide;DIHYDROXYINDOLINEHYDROBROMIDE;1H-Indole-5,6-diol,2,3-dihydro-;2,3-dihydro-1H-Indole-5,6-diol;5,6-Indolinediol;Leucodopaminechrome;Leucodopaminochrome
• CAS NO: 29539-03-5
• Molecular Formula: C8H9NO2
• Molecular Weight: 151.16256
• Mol File: 29539-03-5.mol

Chemical Properties

• Boiling Point: 378.8 °C at 760 mmHg
• Flash Point: 218 °C
• Appearance: /
• Density: 1.356
• Vapor Pressure: 8.18E-07mmHg at 25°C
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 10.29±0.20(Predicted)
• CAS DataBase Reference: 5,6-DIHYDROXYINDOLINE HBR(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DIHYDROXYINDOLINE HBR(29539-03-5)
• EPA Substance Registry System: 5,6-DIHYDROXYINDOLINE HBR(29539-03-5)

Safety Data

• Hazardous Substances Data: 29539-03-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H9NO2.BrH/c10-7-3-5-1-2-9-6(5)4-8(7)11;/h3-4,9-11H,1-2H2;1H

Upstream product

• 62-31-7 dopamine hydrochloride 
• 51-61-6 dopamine 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 6275-29-2 N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide 
• 74064-26-9 N-[2-(2-bromo-4,5-dimethoxyphenyl)ethyl]acetamide 
• 15937-10-7 1-acetyl-2,3-dihydro-5,6-dimethoxy-1H-indole 
• 91361-04-5 N-<2-(2-Brom-4,5-dimethoxyphenyl)-ethyl>-2,2-dimethylpropionsaeureamid 
• 42600-75-9 N-<2-(3,4-Dimethoxyphenyl)-ethyl>-2,2-dimethylpropionsaeureamid 
• 66384-45-0 N-acetyl-2-iodo-4,5-dimethoxy-β-phenethylamine 

Relevant articles and documents

Anaerobic oxidation of dopamine by iron(III)

Iron(III) [in the form of Fe(OH)2+] reacted reversibly in acid aqueous solution with dopamine, 2-(3,4-dihydroxyphenyl)ethylamine (H2LH+, in which the phenolic protons are written to the left of L) to give the complex ion Fe(LH)2+. This species then decomposed to yield iron(II) and a semiquinone, which in turn is oxidised further to a quinone. The latter cyclised to form leucodopaminochrome (indoline-5,6-diol), which was finally oxidised by iron(III) to pink dopaminochrome (6-hydroxy-3H-indol-5-one), presumably via another semiquinone. The rate of appearance and disappearance of the complex and of the ortho-quinone were separately followed by stopped-flow photometric methods. Mechanisms are proposed for the various steps and these are supported by measurements at varying ionic strengths. Rate constants for the reversible formation of the iron-dopamine complex have been evaluated [k1 = (2.09 ± 0.05) × 103 and k-1 = 23 ± 2 dm3 mol-1 s-1]. The rate of decomposition of the protonated complex to yield iron(II) and the semiquinone was established as k2 = 0.23 ± 0.02 s-1 and KMH = 33 ± 0.9 dm3 mol-1 [for the protonation of Fe(LH)2+]. The stability constant of the Fe(LH)2+ complex has been calculated (log K1M = 21.14) and εmax is 1260 dm3 mol-1 cm-1 at 700 nm. The effect of chloride on the rate of complex formation at low pH has been explained by the fact that FeCl2+ also reacts with dopamine (kCl = 148 ± 7 dm3 mol-1 s-1) to form the complex but that this is predominantly reversible via the non-chloride route at low pH values. The stability constant for FeCl2+ formation (a constant not readily accessible by standard methods) was extracted from the data (log K1Cl = 1.53). The rate of disappearance of the quinone enabled the ring-closure reaction (i.e. the formation of the indole) to be followed and the mechanism established. All measurements were carried out at 25°C in solutions of ionic strength 0.10 mol dm-3 (KNO3) except for ionic strength dependence studies.

Enhanced study and control of analyte oxidation in electrospray using a thin-channel, planar electrode emitter

A thin-channel, planar electrode emitter device is described and utilized for the study and control of electrochemical oxidation of analytes at the emitter electrode in an electrospray ion source. For analytes that are not particularly susceptible to oxid

METAL-ORGANIC FRAMEWORKS FOR ELECTROCHEMICAL DETECTION OF ANALYTES

In some embodiments, the present disclosure pertains to methods of detecting an analyte in a sample by associating the sample with an electrode that includes a metal-organic framework. After association, the redox properties of the electrode are evaluated. Thereafter, the presence or absence of the analyte in the sample is detected by correlating the redox properties of the electrode to the presence or absence of the analyte. In some embodiments, the present disclosure pertains to electrodes that include a metal-organic framework and an electrode surface. In particular embodiments of the present disclosure, the metal-organic framework is associated with the electrode surface. Additional embodiments of the present disclosure pertain to methods of making the electrodes of the present disclosure by associating a metal-organic framework with an electrode surface. In some embodiments, the methods of the present disclosure also include a step of mixing the metal-organic framework with a polymer.

Preparation method of compound 5,6-dihydroxy indoline and halogen acid salts thereof

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