10081-39-7

Basic information

• Product Name: 2,6-DIPHENYL-4-(2,4,6-TRIPHENYL-1-PYRIDINIO)PHENOLATE
• Synonyms: 2,6-DIPHENYL-4-(2,4,6-TRIPHENYL-1-PYRIDINIO)PHENOLATE;2,6-DIPHENYL-4-(2,4,6-TRIPHENYLPYRIDINIO)PHENOLATE;REICHARDT'S DYE;2,6-Diphenyl-4-(2,4,6-triphenyl-1-pyridinio)phenolate, 2,6-Diphenyl-4-(2,4,6-triphenylpyridinio)phenolate;1-(4-Oxylato-3,5-diphenylphenyl)-2,4,6-triphenylpyridinium;2,4,6-Triphenyl-1-(2'-oxylato-1,1':3',1''-terbenzene-5'-yl)pyridinium;2,6-Diphenyl-4-(2,4,6-triphenylpyridinio)benzene-1-olate;4-(2,4,6-Triphenylpyridinio)-2,6-diphenylphenolate
• CAS NO: 10081-39-7
• Molecular Formula: C₄₁H₂₉NO
• Molecular Weight: 551.68
• Product Categories: Heterocyclic Compounds
• Mol File: 10081-39-7.mol

Chemical Properties

• Melting Point: 271-275 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: black-violet glittering crystals
• Density: g/cm³
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly, Sonicated)
• Stability: Stable. Incompatible with acids and strong oxidizing agents.
• BRN: 1444580
• CAS DataBase Reference: 2,6-DIPHENYL-4-(2,4,6-TRIPHENYL-1-PYRIDINIO)PHENOLATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIPHENYL-4-(2,4,6-TRIPHENYL-1-PYRIDINIO)PHENOLATE(10081-39-7)
• EPA Substance Registry System: 2,6-DIPHENYL-4-(2,4,6-TRIPHENYL-1-PYRIDINIO)PHENOLATE(10081-39-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 10081-39-7(Hazardous Substances Data)

Usage

Chemical Properties

black-violet glittering crystals

InChI:InChI=1/C41H29NO/c43-41-37(31-18-8-2-9-19-31)28-36(29-38(41)32-20-10-3-11-21-32)42-39(33-22-12-4-13-23-33)26-35(30-16-6-1-7-17-30)27-40(42)34-24-14-5-15-25-34/h1-29H

Synthetic route

2,6-diphenyl-p-aminophenol (50432-01-4) + 2,4,6-Triphenylpyrylium hydrogen sulfate → betaine 30 (10081-39-7)

Conditions	Yield
With sodium hydroxide; sodium acetate 1.) 95percent aq. EtOH, reflux, 3 h; Yield given. Multistep reaction;

N-(3,5-diphenyl-4-hydroxyphenyl)-2,4,6-triphenylpyridinium perchlorate → betaine 30 (10081-39-7)

4-(2,4,6-triphenylpyridinio)-2,6-diphenylphenol (47843-41-4) → betaine 30 (10081-39-7)

Conditions	Yield
With tetrabutyl ammonium fluoride
With tetrabutylammonium dihydrogen phosphate

(1,1';3',1''-terphenyl)-2'-ol (2432-11-3) → betaine 30 (10081-39-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 55 percent / 65percent aq. HNO3 / Ambient temperature 2: 85 percent / Na2S2O4 / aq. NaOH / 0.25 h / Heating 3: 1.) NaOAc, 2.) 5percent aq. NaOH / 1.) 95percent aq. EtOH, reflux, 3 h View Scheme

2,6-diphenyl-4-nitrophenol (2423-73-6) → betaine 30 (10081-39-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / Na2S2O4 / aq. NaOH / 0.25 h / Heating 2: 1.) NaOAc, 2.) 5percent aq. NaOH / 1.) 95percent aq. EtOH, reflux, 3 h View Scheme

tetra(n-butyl)ammonium hydroxide (2052-49-5) + N-(3,5-diphenyl-4-hydroxyphenyl)-2,4,6-triphenylpyridinium perchlorate → betaine 30 (10081-39-7)

Conditions	Yield
In methanol

tetrafluoroboric acid + betaine 30 (10081-39-7) → 1-(3,5-diphenyl-4-hydroxyphenyl)-2,4,6-triphenylpyridin-1-ium tetrafluoroborate

Conditions	Yield
In water for 2h; Schlenk technique;	99%
In water for 2h; Schlenk technique;	99%

betaine 30 (10081-39-7) → 1-(3,5-diphenyl-4-hydroxyphenyl)-2,4,6-triphenylpyridin-1-ium chloride

Conditions	Yield
With hydrogenchloride In diethyl ether; dichloromethane for 0.166667h; Schlenk technique;	96%

betaine 30 (10081-39-7) + Mo(N-adamant-1-yl)(CHCMe2Ph)(OTf)2(dimethoxyethane) → C102H85MoN3O2(2+)*2CF3O3S(1-)

Conditions	Yield
In diethyl ether; chloroform at 20℃; for 0.5h; Inert atmosphere; Glovebox;	92%

betaine 30 (10081-39-7) + Mo(N-2,6-i-Pr2C6H3)(CHCMe2Ph)(OTf)2(DME) (645391-49-7) → C104H87MoN3O2(2+)*2CF3O3S(1-)

Conditions	Yield
In diethyl ether; dichloromethane at 20℃; for 0.5h; Inert atmosphere; Glovebox;	86%

betaine 30 (10081-39-7) + Mo(N-2,6-Me2-C6H3)(CHCMe2Ph)(OTf)2*dimethoxyethane → C100H79MoN3O2(2+)*2CF3O3S(1-)

Conditions	Yield
In diethyl ether; dichloromethane at 20℃; for 0.5h; Inert atmosphere; Glovebox;	78%

betaine 30 (10081-39-7) + Mo(N-2-CF3C6H4)(CHCMe2Ph)(OTf)2(dme) → C99H74F3MoN3O2(2+)*2CF3O3S(1-)

Conditions	Yield
In diethyl ether; dichloromethane at 20℃; for 1h; Inert atmosphere; Glovebox;	75%

betaine 30 (10081-39-7) + Mo(N-2,6-Cl2-C6H3)(CHCMe3)(OTf)2(DME) → C54H42Cl2F6MoN2O7S2

Conditions	Yield
In diethyl ether; dichloromethane at 20℃; for 1h; Inert atmosphere; Glovebox;	75%

betaine 30 (10081-39-7) + Mo(N-2,6-Cl2-C6H3)(CHCMe3)(OTf)2(DME) → C93H71Cl2MoN3O2(2+)*2CF3O3S(1-)

Conditions	Yield
In diethyl ether; dichloromethane at 20℃; for 1h; Inert atmosphere; Glovebox;	69%

betaine 30 (10081-39-7) → 4-(2,4,6-triphenylpyridinio)-2,6-diphenylphenol (47843-41-4)

Conditions	Yield
With carbon dioxide In chloroform; water at 25℃;

betaine 30 (10081-39-7) → 1-(2'-hydroxy-[1,1';3',1'']terphenyl-5'-yl)-2,4,6-triphenyl-pyridinium; iodide

Conditions	Yield
Multi-step reaction with 2 steps 1: CO2 / CHCl3; H2O / 25 °C 2: tetrabutylammonium iodide View Scheme

betaine 30 (10081-39-7) + [Mo(NtBu)(CHCMe2Ph)(4,5-dichloro-1,3-dimethylimidazol-2-ylidene)(OTf)2] → [Mo(NtBu)(CHCMe2Ph)(4,5-dichloro-1,3-dimethylimidazol-2-ylidene)(OTf)(2,6-Ph-4-{2,4,6-Ph-pyridinium}phenolate)][OTf] + [Mo(NtBu)(CHCMe2Ph)(4,5-dichloro-1,3-dimethylimidazol-2-ylidene)2(THF)(2,6-Ph-4-{2,4,6-Ph-pyridinium}phenolate)][OTf]2

Conditions	Yield
In dichloromethane at -40 - 20℃; for 0.5h; Overall yield = 79 %;

betaine 30 (10081-39-7) → C69H66MoN3O(1+)*CF3O3S(1-)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride / dichloromethane; diethyl ether / 0.17 h / Schlenk technique 2: dichloromethane / 0.5 h / 20 °C / Schlenk technique 3: diethyl ether / 0.5 h / -35 °C / Inert atmosphere; Glovebox View Scheme

betaine 30 (10081-39-7) → 1-(3,5-diphenyl-4-hydroxyphenyl)-2,4,6-triphenylpyridin-1-ium triflate

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / dichloromethane; diethyl ether / 0.17 h / Schlenk technique 2: dichloromethane / 0.5 h / 20 °C / Schlenk technique View Scheme

betaine 30 (10081-39-7) → C24BF20(1-)*C41H30NO(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1: water / 2 h / Schlenk technique 2: dichloromethane / 20 °C / Schlenk technique View Scheme

Upstream product

• 50432-01-4 2,6-diphenyl-p-aminophenol 
• 51071-75-1 2,4,6-Triphenylpyrylium hydrogen sulfate 
• 47843-41-4 4-(2,4,6-triphenylpyridinio)-2,6-diphenylphenol 
• 2052-49-5 tetra(n-butyl)ammonium hydroxide 
• 2423-73-6 2,6-diphenyl-4-nitrophenol 
• 2432-11-3 (1,1';3',1''-terphenyl)-2'-ol 

Downstream Products

• 47843-41-4 4-(2,4,6-triphenylpyridinio)-2,6-diphenylphenol 

Relevant articles and documents

THE POLARITY OF ALCOHOLIC ELECTROLYTE SOLUTIONS. A SYSTEMATIC STUDY

The ET(30) polarity values of alcoholic salt solutions were determined for twenty salt/solvent combinations.In all cases equation correlates accurately the medium polarity with the salt concentration.The meaning of this equation is discussed in terms of possible interactions in solution.The dye (1) is shown to be a useful probe for the cationic environment of salts in solution.

An anionic chromogenic sensor based on protonated Reichardt's pyridiniophenolate

An anionic sensor based on Reichardt's betaine is described here. The dye is blue-green in chloroform but becomes colorless under protonation. Increasing amounts of different anions were added into the solution of the protonated dye. The addition of F- and H 2 PO4- caused the reappearance of the original blue-green color, while the addition of I- made the solution of the protonated dye yellow. The observations are discussed based on the fact that F- and H 2 PO4- can act as bases accepting a proton from the protonated dye and also in relation to the formation of a complex between the protonated dye and iodide.

An Improved Synthesis of the Solvatochromic Dye ET-30

An improved synthesis of the well-known dye ET-30, which is used as a standard for the characterization of solvent polarity, using easily available starting materials is described.

The positive halochromism of phenolate dyes in hydroxylic solutions of tetraalkylammonium cations

By contrast with the negative halochromic behaviour shown by phenolate betaines in the presence of alkaline and alkaline-earth cations, the addition of tetraalkylammonium salts to hydroxylic solutions of these dyes generate bathochromic shifts of their charge-transfer band. This positive halochromic behaviour by organic cations was examined systematically and its origin rationalized by nonspecific changes of the medium permittivity, and by specific dye-cation interactions in solution.