956-48-9

Basic information

• Product Name: 2,6-DICHLOROPHENOLINDOPHENOL
• Synonyms: 2,6-dichloroindophenol;PHENOLINDO-2,6-DICHLOROPHENOL;2,6-DICHLOROPHENOLINDOPHENOL;2,6-dichloro-N-4-hydroxyphenyl-p-benzoquinone monoimine;DCPIP;Dichloroindophenol;Dichlorophenolindphenol;Indochlorophenol
• CAS NO: 956-48-9
• Molecular Formula: C₁₂H₇Cl₂NO₂
• Molecular Weight: 268.1
• EINECS: 213-479-8
• Mol File: 956-48-9.mol

Chemical Properties

• Boiling Point: 393.5 °C at 760 mmHg
• Flash Point: 191.8 °C
• Appearance: /
• Density: 1.43 g/cm³
• Vapor Pressure: 9.34E-07mmHg at 25°C
• Refractive Index: 1.633
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 10.49±0.30(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 2,6-DICHLOROPHENOLINDOPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DICHLOROPHENOLINDOPHENOL(956-48-9)
• EPA Substance Registry System: 2,6-DICHLOROPHENOLINDOPHENOL(956-48-9)

Safety Data

• Hazardous Substances Data: 956-48-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Biomedical Research:
2,6-Dichlorophenolindophenol is used as a redox indicator for assessing the ascorbic acid content in various samples. Ascorbic acid, also known as vitamin C, is an essential nutrient with antioxidant properties that plays a crucial role in various biological processes. The ability of indophenol to change color upon reduction by ascorbic acid makes it a reliable and sensitive method for determining the vitamin C content in pharmaceutical formulations, food products, and biological samples.
Used in Chemical and Environmental Analysis:
In addition to its use in assessing ascorbic acid content, 2,6-dichlorophenolindophenol can also be employed as a redox dye in other chemical and environmental analyses. Its redox properties allow it to be used in the detection and quantification of various substances, as well as in the study of redox processes in different systems.
Used in Educational Purposes:
2,6-Dichlorophenolindophenol can be utilized as a teaching tool in educational settings, particularly in chemistry and biology courses. Demonstrating the redox reactions involving indophenol can help students understand the principles of redox chemistry and the importance of antioxidants like ascorbic acid in biological systems.

InChI:InChI=1/C12H7Cl2NO2/c13-10-5-8(6-11(14)12(10)17)15-7-1-3-9(16)4-2-7/h1-6,16H

Synthetic route

4-amino-2,6-dichlorophenol (5930-28-9) → 2,6-Dichlorophenolindophenol (956-48-9)

Conditions	Yield
With sodium hypochlorite

2,6-dichloroindophenol acetate (24857-20-3) → 2,6-Dichlorophenolindophenol (956-48-9)

Conditions	Yield
With human recombinant acetylcholinesterase; water In aq. phosphate buffer; ethanol pH=7.4; Enzymatic reaction;

2,6-Dichlorophenolindophenol (956-48-9) → 2,6-Dichloroindophenol reduced (2099-87-8)

Conditions	Yield
With [NiIICl(N,N’-dimethyl-3,7-diazanonane-1,9-dithiolato)IrIIICl(η5-C5Me5)]; hydrogen In water at 60℃; under 6000.6 Torr; for 2h; pH=4 - 10; Catalytic behavior; Reagent/catalyst; pH-value; Temperature; Pressure; Glovebox; Schlenk technique;	84%
With hydrogen; [NiIICl(XN,N'-dimethyl-3,7-diazanonane-1,9-dithiolato)(μ-H)RhIII(η5-C5Me5)] In aq. phosphate buffer; water at 20℃; for 0.583333h; pH=7; Inert atmosphere; Schlenk technique; Glovebox;	78%
With phosphate buffer (NaH2PO4, Na2HPO4); potassium chloride; sodium thiosulfate In methanol; water at 30℃; Rate constant; Thermodynamic data; ΔH(excit.), ΔS(excit.), ΔG(excit.); var. conc. of sodium thiosulphate and 2,6-dichlorophenolindophenol;

2,6-Dichlorophenolindophenol (956-48-9) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2,6-dichlorophenolindophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (129253-64-1) + phenolindo-3',5'-dichlorophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (122078-53-9)

Conditions	Yield
With silver(l) oxide In benzene Heating;	A 38.8% B 10.8%

2,6-Dichlorophenolindophenol (956-48-9) + NADH (58-68-4) → NAD (53-84-9)

Conditions	Yield
With ethylenediaminetetraacetic acid In various solvent(s) at 30℃; pH=8.0; Enzyme kinetics;

2,6-Dichlorophenolindophenol (956-48-9) + ascorbic acid (50-81-7) → 2,6-Dichloroindophenol reduced (2099-87-8) + L-dehydroascorbic acid (490-83-5)

Conditions	Yield
With hydrogenchloride In water pH=2 - 7; Kinetics; Time; aq. acetate buffer;

2,6-Dichlorophenolindophenol (956-48-9) + L-proline (147-85-3) → 2,6-Dichloroindophenol reduced (2099-87-8) + Δ1-pyrroline-5-carboxylic acid (64199-88-8)

Conditions	Yield
With l-proline dehydrogenase In aq. buffer pH=8; Reagent/catalyst; Enzymatic reaction;

Upstream product

• 5930-28-9 4-amino-2,6-dichlorophenol 
• 24857-20-3 2,6-dichloroindophenol acetate 

Downstream Products

• 2099-87-8 2,6-Dichloroindophenol reduced 
• 64199-88-8 Δ¹-pyrroline-5-carboxylic acid 
• 129253-64-1 2,6-dichlorophenolindophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 122078-53-9 phenolindo-3',5'-dichlorophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 490-83-5 L-dehydroascorbic acid 
• 53-84-9 NAD 

Relevant articles and documents

Evaluation of 2,6-dichlorophenolindophenol acetate as a substrate for acetylcholinesterase activity assay

Ellman's method is a standard protocol for the determination of cholinesterases activity. Though the method is ready for laboratory purposes, it has some drawbacks as well. In the current article, 2,6-dichloroindophenol acetate is performed as a chromogenic substrate suitable for acetylcholinesterase (AChE) activity examination. Michaelis constant and maximal velocity for 2,6-dichloroindophenol acetate were determined (38.0 μM and 244 pkat) and compared to the values for acetythiocholine (Km 0.18 mM; Vmax 5.1 nkat). Docking for 2,6-dichloroindophenol acetate and human AChE was done as well. In conclusion, 2,6-dichloroindophenol acetate seems to be suitable chromogenic substrate for AChE and spectrophotometry and based on this it can be easily performed whenever AChE activity should be tested.