603-44-1

Basic information

• Product Name: 4,4',4''-TRIHYDROXYTRIPHENYLMETHANE
• Synonyms: trihydroxytriphenylmethane;TRIS(4-HYDROXYPHENYL)METHANE;4,4',4''-METHYLIDYNETRISPHENOL;4,4',4''-METHYLIDYNETRIPHENOL;4,4',4''-TRIHYDROXYTRIPHENYLMETHANE;LEUCAURIN;Tri(4-Hydroxyphenyl) Methane;4,4',4'-METHYLIDYNETRIPHENOL(TRI(4-HYDROXYPHENYL) METHANE)
• CAS NO: 603-44-1
• Molecular Formula: C₁₉H₁₆O₃
• Molecular Weight: 292.33
• EINECS: 210-040-2
• Mol File: 603-44-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: 247 °C
• Boiling Point: 503.8 °C at 760 mmHg
• Flash Point: 239.6 °C
• Appearance: /
• Density: 1.282 g/cm³
• Vapor Pressure: 8.98E-11mmHg at 25°C
• Refractive Index: 1.674
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• PKA: 9.83±0.10(Predicted)
• CAS DataBase Reference: 4,4',4''-TRIHYDROXYTRIPHENYLMETHANE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4',4''-TRIHYDROXYTRIPHENYLMETHANE(603-44-1)
• EPA Substance Registry System: 4,4',4''-TRIHYDROXYTRIPHENYLMETHANE(603-44-1)

Safety Data

• Hazardous Substances Data: 603-44-1(Hazardous Substances Data)

Usage

General Description

4,4',4''-Trihydroxytriphenylmethane is a chemical compound with the molecular formula C21H16O3. It is a triphenylmethane dye that is typically used as a dye intermediate in the production of colorants for textiles, plastics, and other materials. 4,4',4''-TRIHYDROXYTRIPHENYLMETHANE is a crystalline solid that is insoluble in water but soluble in organic solvents. It is produced by the condensation of phenol and benzaldehyde in the presence of an acid catalyst. 4,4',4''-Trihydroxytriphenylmethane has been used in various applications, including as a coloring agent for plastics and as a developer in photography. However, it is important to handle this compound with care due to its potential health and environmental hazards.

InChI:InChI=1/C19H16O3/c20-16-7-1-13(2-8-16)19(14-3-9-17(21)10-4-14)15-5-11-18(22)12-6-15/h1-12,19-22H

Synthetic route

tris(4-methoxyphenyl)methanol (3010-81-9) → 4,4',4''-methylidynetrisphenol (603-44-1)

Conditions	Yield
With sodium thioethylate In N,N-dimethyl-formamide for 24h; Heating;	93%
With sodium thioethylate In N,N-dimethyl-formamide for 9h; Heating;	93%

carbon monoxide (201230-82-2) + phenol (108-95-2) → bis-(4-hydroxyphenyl)methane (620-92-8) + 4,4',4''-methylidynetrisphenol (603-44-1) + 4-hydroxy-benzaldehyde (123-08-0) + salicylaldehyde (90-02-8)

Conditions	Yield
With hydrogen fluoride; boron trifluoride at 45℃; under 37503.8 - 60006 Torr; for 4.5h; Product distribution; Further Variations:; Reagents; time;	A n/a B n/a C 80% D 6%

N-(4-hydroxybenzylidene)-4-methylbenzenesulfonamide + phenol (108-95-2) → 4,4',4''-methylidynetrisphenol (603-44-1)

Conditions	Yield
With chloro-trimethyl-silane; bismuth(III) sulfate In dichloromethane at 20℃; for 12h; Friedel-Crafts reaction;	80%

aurin (603-45-2) → 4,4',4''-methylidynetrisphenol (603-44-1)

Conditions	Yield
With sodium tetrahydroborate; acetic acid In ethanol	76%

4-hydroxy-benzaldehyde (123-08-0) + phenol (108-95-2) → 4,4',4''-methylidynetrisphenol (603-44-1)

Conditions	Yield
With toluene-4-sulfonic acid; zinc(II) chloride at 45℃; for 25h;	70%
With sulfuric acid; acetic acid
With phosphoric acid
With sulfuric acid In 1,4-dioxane; water at 20℃; for 6h;
With toluene-4-sulfonic acid; zinc(II) chloride

chloroform (67-66-3) + potassium phenolate (100-67-4) → 4,4',4''-methylidynetrisphenol (603-44-1)

Conditions	Yield
bei Abwesenheit von Sauerstoff;

tetrachloromethane (56-23-5) + phenol (108-95-2) → 4,4',4''-methylidynetrisphenol (603-44-1)

Conditions	Yield
With zinc(II) chloride at 135℃;

aurin (603-45-2) → 5,6-dihydro-3,5,5-trimethyl-1,4-oxazin-2-one (53153-46-1) + 4,4',4''-methylidynetrisphenol (603-44-1)

Conditions	Yield
With 3,5,5-trimethyl-2-morpholinon-3-yl In dimethylsulfoxide-d6 at 50℃; Yield given. Title compound not separated from byproducts;

dichloromethane (75-09-2) + phenol (108-95-2) → 2-[(4-hydroxyphenyl)methyl]phenol (2467-03-0) + bis-(4-hydroxyphenyl)methane (620-92-8) + 4,4',4''-methylidynetrisphenol (603-44-1) + 2-hydroxyphenylphenoxymethane (76176-97-1)

Conditions	Yield
at 15℃; for 48h; Irradiation; Further byproducts given;

tetrachloromethane (56-23-5) + (E)-3-Ureido-but-2-enoic acid ethyl ester (5435-44-9, 22243-66-9) + phenol (108-95-2) → aurin (603-45-2) + 4,4',4''-methylidynetrisphenol (603-44-1) + (2-Hydroxy-phenyl)-bis-(4-hydroxy-phenyl)-methanol + 2'.4''-dioxy-fuchsone

Conditions	Yield
at 135℃; Produkt: 9-<4-Oxy-phenyl>-xanthen, 9-<4-Oxy-phenyl>-fluoron;

chloroform (67-66-3) + potassium phenolate (100-67-4) + nitrogen → Orthoameisensaeuretriphenylester (16737-44-3) + 4,4',4''-methylidynetrisphenol (603-44-1)

Conditions	Yield
at 110℃;

aurin (603-45-2) + acetic acid (64-19-7) + zinc → 4,4',4''-methylidynetrisphenol (603-44-1)

aurin (603-45-2) + zinc + alkali → 4,4',4''-methylidynetrisphenol (603-44-1)

4'.4''-dioxy-fuchsone → 4,4',4''-methylidynetrisphenol (603-44-1)

Conditions	Yield
With sodium hydroxide; zinc
With acetic acid; zinc

diazotized <4-amino-phenyl>-bis-<4-hydroxy-phenyl>-methane → 4,4',4''-methylidynetrisphenol (603-44-1)

Conditions	Yield
With water

sodium salt of/the/ aurinleucosulfinic acid → 4,4',4''-methylidynetrisphenol (603-44-1)

Conditions	Yield
With alkaline solution

tris-(4-hydroxy-phenyl)-methanesulfinic acid ; sodium salt + alkalies → 4,4',4''-methylidynetrisphenol (603-44-1) + sodium sulfite

Conditions	Yield
Erwaermen;

1-bromo-4-methoxy-benzene (104-92-7) → 4,4',4''-methylidynetrisphenol (603-44-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 51 percent 2: 93 percent / NaSEt / dimethylformamide / 24 h / Heating View Scheme

bis(p-methoxyphenyl)methanone (90-96-0) → 4,4',4''-methylidynetrisphenol (603-44-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 51 percent 2: 93 percent / NaSEt / dimethylformamide / 24 h / Heating View Scheme

3,4-dihydro-2H-pyran (110-87-2) + bromoacetic acid (79-08-3) → 4,4',4''-methylidynetrisphenol (603-44-1)

Conditions	Yield
With toluene-4-sulfonic acid In tetrahydrofuran

4''-hydroxy-4,4'-dimethoxytriphenylmethane → 4,4',4''-methylidynetrisphenol (603-44-1)

Conditions	Yield
With boron tribromide In dichloromethane at -78 - 20℃;

formaldehyd (50-00-0) + 4,4',4''-methylidynetrisphenol (603-44-1) + dimethyl amine (124-40-3) → 2,2',2'',6,6',6''-hexakis(dimethylaminomethyl)-4,4',4''-trihydroxytriphenylmethane (1272320-14-5)

Conditions	Yield
In ethanol; water at 0 - 100℃;	95%

4,4',4''-methylidynetrisphenol (603-44-1) + 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride (36451-09-9) → C49H28N6O12S3

Conditions	Yield
With triethylamine In acetone at 20℃; for 3h;	89.5%

4,4',4''-methylidynetrisphenol (603-44-1) + phosphonic acid diethyl ester (762-04-9) → C31H43O12P3 (1262222-43-4)

Conditions	Yield
With triethylamine In tetrachloromethane at 0 - 20℃; for 17h;	89%

4,4',4''-methylidynetrisphenol (603-44-1) + 3,5-bis(benzylamino)benzoic acid → C82H70N6O6

Conditions	Yield
With 2-(dimethylamino)pyridinium p-toluenesulfonate; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h;	81%

trifluoromethane sulfonyl chloride (421-83-0) + 4,4',4''-methylidynetrisphenol (603-44-1) → trifluoromethanesulfonic acid methylidynetri-4,1-phenylene ester (848859-63-2)

Conditions	Yield
With dmap; triethylamine In acetone at 0℃; for 3h;	80%

trifluoromethylsulfonic anhydride (358-23-6) + 4,4',4''-methylidynetrisphenol (603-44-1) → trifluoromethanesulfonic acid methylidynetri-4,1-phenylene ester (848859-63-2)

Conditions	Yield
With pyridine at 0 - 20℃; for 12h; Inert atmosphere;	80%

4,4',4''-methylidynetrisphenol (603-44-1) + 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) → 2,2',2''-(4,4',4''-methanetriyltris(benzene-4,1-diyl)tris(oxy))tris(N,N-diethylethanamine) (1206894-03-2)

Conditions	Yield
With potassium carbonate In acetone Reflux;	79%

4,4',4''-methylidynetrisphenol (603-44-1) + propargyl bromide (106-96-7) → Tris<4-(2-propinyloxy)phenyl>methan (122035-55-6)

Conditions	Yield
With potassium carbonate In acetone for 3h; Heating;	74%

4,4',4''-methylidynetrisphenol (603-44-1) + propargyl bromide (106-96-7) → Tris<4-(2-propinyloxy)phenyl>methan (122035-55-6) + (4-Hydroxyphenyl)bis<4-(2-propinyloxy)phenyl>methan (140149-18-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 5h;	A 74% B 19%

4,4',4''-methylidynetrisphenol (603-44-1) + C49H44N2O6 → C166H142N6O18

Conditions	Yield
With 2-(dimethylamino)pyridinium p-toluenesulfonate; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h;	70%

4,4',4''-methylidynetrisphenol (603-44-1) + propargyl bromide (106-96-7) → (4-Hydroxyphenyl)bis<4-(2-propinyloxy)phenyl>methan (140149-18-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 5h;	69%

1-bromomethyl-4-iodobenzene (16004-15-2) + 4,4',4''-methylidynetrisphenol (603-44-1) → tris(4((4-iodobenzyl)oxy)phenyl)methane

Conditions	Yield
With caesium carbonate In acetonitrile at 60℃; for 10h; Inert atmosphere;	69%

2-[2-(chloroethoxy)ethoxy]ethanol (5197-62-6) + 4,4',4''-methylidynetrisphenol (603-44-1) → C37H52O12 (1239678-24-0)

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 100℃;	65%

morpholine (110-91-8) + formaldehyd (50-00-0) + 4,4',4''-methylidynetrisphenol (603-44-1) → tris(4-hydroxy-3-morpholinomethylphenyl)methane (946513-74-2)

Conditions	Yield
Stage #1: morpholine; 4,4',4''-methylidynetrisphenol In toluene at 25℃; for 0.5h; Stage #2: formaldehyd In toluene at 39 - 45℃; for 17h; Stage #3: morpholine; formaldehyd In toluene for 6.16667h;	63.9%

4,4',4''-methylidynetrisphenol (603-44-1) + 3,4,5-tris(n-dodecan-1-yloxy)benzyl chloride (162709-84-4) → tris[4-(3,4,5-tridodecyloxybenzyloxy)phenyl]methane (1063745-70-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 6h;	61%

1,1,1-tris(4-hydroxyphenyl)ethane (27955-94-8) + 4,4',4''-methylidynetrisphenol (603-44-1) → C167H144N6O18

Conditions	Yield
With 2-(dimethylamino)pyridinium p-toluenesulfonate; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h;	49%

4,4',4''-methylidynetrisphenol (603-44-1) + phenoxyethyl bromide (589-10-6) → C35H32O5 (1632225-39-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;	40%

4,4',4''-methylidynetrisphenol (603-44-1) + phenoxyethyl bromide (589-10-6) → C43H40O6 (1632225-42-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;	25%

4,4',4''-methylidynetrisphenol (603-44-1) + acetic anhydride (108-24-7) → tris-(4-acetoxy-phenyl)-methane

4,4',4''-methylidynetrisphenol (603-44-1) + benzoyl chloride (98-88-4) → tris-(4-benzoyloxy-phenyl)-methane

4,4',4''-methylidynetrisphenol (603-44-1) + acetyl chloride (75-36-5) → tris-(4-acetoxy-phenyl)-methane

4,4',4''-methylidynetrisphenol (603-44-1) + dimethyl sulfate (77-78-1) → tris(4-methoxyphenyl)methane (7511-68-4)

Upstream product

• 67-66-3 chloroform 
• 100-67-4 potassium phenolate 
• 56-23-5 tetrachloromethane 
• 108-95-2 phenol 
• 3010-81-9 tris(4-methoxyphenyl)methanol 
• 201230-82-2 carbon monoxide 
• 90-96-0 bis(p-methoxyphenyl)methanone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 603-45-2 aurin 
• 110-87-2 3,4-dihydro-2H-pyran 
• 79-08-3 bromoacetic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 64-19-7 acetic acid 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 

Downstream Products

• 848859-63-2 trifluoromethanesulfonic acid methylidynetri-4,1-phenylene ester 
• 140149-21-9 2,6-Bis<4-methyl>phenoxymethyl>pyridin 
• 916657-15-3 [Cu(2,9-dimethyl-1,10-phenanthroline)2][tris(4-hydroxyphenyl)methane^(1-))] 
• 1262222-43-4 C₃₁H₄₃O₁₂P₃ 
• 7511-68-4 tris(4-methoxyphenyl)methane 
• 1632225-39-8 C₃₅H₃₂O₅ 

Relevant articles and documents

Hydrogen-bond networks in tris(4-hydroxyphenyl)methane and its 1:1 Molecular complex with 4,4′-bipyridine

In tris(4-hydroxyphenyl)methane (or 4,4′,4″-methanetriyltriphenol), C19H16O 3, molecules are connected by O - H...O hydrogen bonds [O...O = 2.662 (2) and 2.648 (2) A] into two-dimensional square networks that are twofold interpenetrated. In tris(4-hydroxyphenyl)methane-4,4′-bipyridine (1/1), C19H 16O3·C10H8N2, trisphenol molecules form rectangular networks via O - H...O [O...O = 2.694 (3) A] and C - H... O [C...O = 3.384 (3) A] hydrogen bonds. Bipyridine molecules hydrogen bonded to phenol moieties [O...N = 2.622 (3) and 2.764 (3) A] fill the voids to complete the structure.

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