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
• Article Data: 1

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

2,6-Dichlorophenolindophenol (Technical Grade) is an organic redox dye, and is commonly used to assess ascorbic acid content.

Definition

ChEBI: A quinone imine that is indophenol substituted by chloro groups at positions 2 and 6.

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

• 53-84-9 NAD 
• 2099-87-8 2,6-Dichloroindophenol reduced 
• 490-83-5 L-dehydroascorbic acid 
• 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