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inquiry4,4'-DIHYDROXYDIPHENYLMETHANE Basic information Product Name: 4,4'-DIHYDROXYDIPHENYLMETHANE Synonyms: 4,4’-methylenebis(phenol;4,4’-methylenebis-pheno;4,4’-meth
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inquiry4,4'-DIHYDROXYDIPHENYLMETHANE Chemical Properties Melting point 162-164 °C Boiling point 297.96°C (rough estimate) density 1.0907 (rough estimate) refractive index 1.6110 (estimate) storage temp. Sealed in dry,Room Tem
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bis(4-hydroxyphenyl)methanol
bis-(4-hydroxyphenyl)methane
Conditions | Yield |
---|---|
With o-benzenedisulfonimide; isopropyl alcohol at 80℃; for 3h; | 100% |
Conditions | Yield |
---|---|
With MIL-101(Cr/Al)A-f at 60℃; for 0.5h; Kinetics; Reagent/catalyst; | 97.1% |
With silica supported perchloric acid In neat (no solvent) for 4.25h; Heating; Green chemistry; | 93% |
With sulfonic acid and mercapto bifunctional modified mesoporous SBA-15 molecular sieve catalyst In water at 80℃; for 2h; Temperature; Inert atmosphere; | 89.4% |
9-fluorenone
phenol
A
bis-(4-hydroxyphenyl)methane
B
9,9-bis(4-hydroxyphenyl)fluorene
Conditions | Yield |
---|---|
With hydrogenchloride In Zinc chloride; water; isopropyl alcohol | A n/a B 97% |
In Zinc chloride; water; isopropyl alcohol | A 81% B n/a |
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol at 20℃; for 6h; | 91% |
With aluminum (III) chloride; lithium aluminium tetrahydride In tetrahydrofuran at 65℃; for 48h; | 68% |
With aluminum (III) chloride; lithium aluminium tetrahydride In tetrahydrofuran at 65℃; for 48h; | 68% |
With hydrogenchloride; amalgamated zinc; toluene | |
With palladium on activated charcoal; isopropyl alcohol Hydrogenation; |
1,1'-bis(-tert-butyldimethylsilyloxy)-4,4'-methylenediphenol
bis-(4-hydroxyphenyl)methane
Conditions | Yield |
---|---|
With potassium hydrogen difluoride In methanol at 20℃; for 2h; | 84% |
carbon monoxide
phenol
A
bis-(4-hydroxyphenyl)methane
B
4,4',4''-methylidynetrisphenol
C
4-hydroxy-benzaldehyde
D
salicylaldehyde
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% |
Conditions | Yield |
---|---|
With pyridine hydrochloride at 210℃; for 0.5h; | 77.5% |
formaldehyd
phenol
A
Bis(2-hydroxyphenyl)methane
B
2-[(4-hydroxyphenyl)methyl]phenol
C
bis-(4-hydroxyphenyl)methane
Conditions | Yield |
---|---|
Stage #1: phenol With catalyst with modified organic framework formed from chromium trioxide and phosphotungstic acid at 80℃; for 0.25h; Stage #2: formaldehyd In water at 80℃; for 0.5h; Concentration; Time; Temperature; Reagent/catalyst; | A 7.03% B 18.73% C 74.24% |
Stage #1: phenol With catalyst with modified organic framework formed from ferric nitrate and phosphotungstic acid at 80℃; for 0.25h; Stage #2: formaldehyd In water at 80℃; for 4h; Concentration; Time; Temperature; Reagent/catalyst; | A 51.19% B 33.7% C 15.11% |
Stage #1: phenol With catalyst with modified organic framework formed from ferric nitrate and phosphotungstic acid at 80℃; for 0.25h; Stage #2: formaldehyd In water at 80℃; for 0.5h; Concentration; Time; Temperature; Reagent/catalyst; | A 30.11% B 50.55% C 19.34% |
Conditions | Yield |
---|---|
With potassium carbonate In ethyl acetate; N,N-dimethyl-formamide | 67% |
bis-(4-hydroxyphenyl)methane
Conditions | Yield |
---|---|
With quinoline; copper(I) oxide; 1,10-Phenanthroline In 1-methyl-pyrrolidin-2-one at 190℃; for 1h; Sealed tube; Microwave irradiation; | 63% |
bis-(4-hydroxyphenyl)methanehydrazone
bis-(4-hydroxyphenyl)methane
Conditions | Yield |
---|---|
With potassium hydroxide; ethylene glycol for 0.00277778h; Wolff-Kishner reduction; Microwave irradiation; | 40% |
Conditions | Yield |
---|---|
With proton exchanged montmorillonite In dichloromethane at 25℃; for 5h; | 5% |
Conditions | Yield |
---|---|
beim Erhitzen ueber den Schmelzpunkt; | |
With alkali | |
With copper(I) oxide; N,N,N,N,-tetramethylethylenediamine In 1-methyl-pyrrolidin-2-one at 185℃; for 20h; |
5,5'-methylenedisalicylic acid
A
bis-(4-hydroxyphenyl)methane
B
2-hydroxy-5-(4-hydroxy-benzyl)-benzoic acid
Conditions | Yield |
---|---|
With potassium hydroxide at 140℃; im Einschlussrohr; |
Conditions | Yield |
---|---|
With cis-nitrous acid |
formaldehyd
phenol
A
2-[(4-hydroxyphenyl)methyl]phenol
B
bis-(4-hydroxyphenyl)methane
Conditions | Yield |
---|---|
With hydrogenchloride; ethanol |
formic acid
(hydroxymethyl)urea
phenol
A
bis-(4-hydroxyphenyl)methane
B
1,3-bis(4-hydroxybenzyl)urea
4,4'-Dihydroxybenzophenone
A
bis-(4-hydroxyphenyl)methane
B
bis(4-hydroxyphenyl)methanol
Conditions | Yield |
---|---|
With hydrogenchloride; sodium cyanoborohydride In tetrahydrofuran for 24h; Product distribution; | A 98 % Spectr. B 2 % Spectr. |
dichloromethane
phenol
A
2-[(4-hydroxyphenyl)methyl]phenol
B
bis-(4-hydroxyphenyl)methane
C
4,4',4''-methylidynetrisphenol
D
2-hydroxyphenylphenoxymethane
Conditions | Yield |
---|---|
at 15℃; for 48h; Irradiation; Further byproducts given; |
dichloromethane
phenol
A
2-[(4-hydroxyphenyl)methyl]phenol
B
bis-(4-hydroxyphenyl)methane
C
2-hydroxyphenylphenoxymethane
Conditions | Yield |
---|---|
at 15℃; for 48h; Irradiation; Further byproducts given; |
formaldehyd
4-[4-(tert-Butyl-dimethyl-silanyloxy)-benzyl]-phenol
A
bis-(4-hydroxyphenyl)methane
Conditions | Yield |
---|---|
With ethylmagnesium bromide; tetrabutyl ammonium fluoride 1.) Et2O, room temperature, 15 min, 2.) C6H6, reflux, 20 h, 3.) THF, 6 h; Yield given. Multistep reaction. Yields of byproduct given; |
hydrogenchloride
formaldehyd
phenol
bis-(4-hydroxyphenyl)methane
hydrogenchloride
formaldehyd
phenol
A
2-[(4-hydroxyphenyl)methyl]phenol
B
bis-(4-hydroxyphenyl)methane
Conditions | Yield |
---|---|
unter Druck.Hydrogenation; |
bis-(4-hydroxyphenyl)methane
Conditions | Yield |
---|---|
With potassium carbonate beim Schmelzen; |
A
bis-(4-hydroxyphenyl)methane
B
3,3'-dihydroxydiphenylmethane
C
3,4'-dihydroxydiphenylmethane
Conditions | Yield |
---|---|
With boric acid tributyl ester; lithium diisopropyl amide In tetrahydrofuran at 0℃; for 5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
5,5'-methylenedisalicylic acid
A
carbon dioxide
B
bis-(4-hydroxyphenyl)methane
C
2-hydroxy-5-(4-hydroxy-benzyl)-benzoic acid
Conditions | Yield |
---|---|
beim Erhitzen ueber den Schmelzpunkt; |
5,5'-methylenedisalicylic acid
A
carbon dioxide
B
bis-(4-hydroxyphenyl)methane
C
2-hydroxy-5-(4-hydroxy-benzyl)-benzoic acid
Conditions | Yield |
---|---|
at 140℃; im Rohr; |
bis-(4-hydroxyphenyl)methane
4-[(4-hydroxyphenyl)methyl]-1,2-benzenediol
Conditions | Yield |
---|---|
With oxygen; ascorbic acid In water; acetonitrile at 20℃; for 48h; pH=7; Na-phosphate buffer; Enzymatic reaction; | 99% |
bis-(4-hydroxyphenyl)methane
bis(diethylamino)phenylphosphine
B
diethylamine
Conditions | Yield |
---|---|
In neat (no solvent) at 115 - 120℃; for 2h; | A 97% B n/a |
propargyl chloroformate
bis-(4-hydroxyphenyl)methane
Conditions | Yield |
---|---|
With trimethylamine In dichloromethane | 93.6% |
With trimethylamine In dichloromethane | 93.6% |
bis-(4-hydroxyphenyl)methane
bromoacetic acid methyl ester
4,4'-bis(methoxycarbonylmethoxy)diphenylmethane
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; | 93% |
bis-(4-hydroxyphenyl)methane
phenyl chloroformate
bis(4-hydroxyphenyl)methane diphenyl dicarbonate
Conditions | Yield |
---|---|
With pyridine; dmap In tetrahydrofuran at 0 - 20℃; | 91.6% |
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 60℃; for 24h; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
With potassium hydroxide In acetone for 16h; Heating; | 88% |
With potassium hydroxide In acetone Inert atmosphere; Reflux; | 88% |
With potassium hydroxide In acetone Inert atmosphere; Reflux; | 88% |
bis-(4-hydroxyphenyl)methane
Conditions | Yield |
---|---|
With Et3N In toluene byproducts: (Et3NH)I; N2-atmosphere; refluxing for 54 h; cooling to room temp., filtration off of Et3NHI, evapn. (vac.), repeatedchromy. (SiO2, CH2Cl2/hexane=1:1 v/v); | 88% |
Conditions | Yield |
---|---|
In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 10h; Mannich Aminomethylation; | 87% |
bis-(4-hydroxyphenyl)methane
benzoyl chloride
bis-(4-benzoyloxy-phenyl)-methane
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 20℃; for 1h; | 86% |
bis-(4-hydroxyphenyl)methane
tetrabromobisphenol-F
Conditions | Yield |
---|---|
With bromine; acetic acid for 2h; | 84% |
With bromine ueber mehrere Stufen; | |
With bromine; acetic acid | |
With bromine; acetic acid at 20℃; for 2h; |
formaldehyd
bis-(4-hydroxyphenyl)methane
aniline
bisphenol F benzoxazine
Conditions | Yield |
---|---|
With water In toluene at 80℃; for 5h; | 83% |
bis-(4-hydroxyphenyl)methane
4,4′-(propane-2,2-diyl)di(benzene-4,1-diyl) bis(N,N-diethyl-P-phenylphosphonamidite)
Conditions | Yield |
---|---|
In toluene at 90 - 95℃; for 4h; | 83% |
Conditions | Yield |
---|---|
Stage #1: 1,2-dibromo-1,1,2,2-tetrafluoroethane; bis-(4-hydroxyphenyl)methane In dimethyl sulfoxide at 60℃; for 20h; Stage #2: With acetic acid; zinc for 36h; | 83% |
bis-(4-hydroxyphenyl)methane
Conditions | Yield |
---|---|
With pyridine; C5H8FN2O2S(1+)*C2H3O3(1-) In acetone at 25℃; for 18h; | 82.3% |
bis-(4-hydroxyphenyl)methane
Conditions | Yield |
---|---|
With sulphamoyl chloride In N,N-dimethyl acetamide at 0 - 20℃; | 81.6% |
bis-(4-hydroxyphenyl)methane
2-chloroetyl vinyl ether
bis(4-(2-(vinyloxy)ethoxy)phenyl)methane
Conditions | Yield |
---|---|
With sodium hydroxide; tetrabutylammomium bromide 1.) toluene, 0.5 h, 80 deg C, 2.) 3 h, 95 deg C; | 79% |
formaldehyd
bis-(4-hydroxyphenyl)methane
4,4'-methylenebis[2,6-bis(hydroxymethyl)phenol]
Conditions | Yield |
---|---|
With sodium hydroxide for 7h; Ambient temperature; | 78% |
With lithium hydroxide | |
With sodium hydroxide In water Ambient temperature; | |
With sodium hydroxide In water at 65℃; for 2h; pH=9 - 10; |
[1,3]-dioxolan-2-one
bis-(4-hydroxyphenyl)methane
2,2′-((methylene-bis(4,4′-phenylene))bis(oxy))diethanol
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide Reflux; | 78% |
2-ethyl-N-(2-ethylhexyl)-1-hexanamine
bis-(4-hydroxyphenyl)methane
4-Nitrophenyl chloroformate
C47H78N2O4
Conditions | Yield |
---|---|
Stage #1: bis-(4-hydroxyphenyl)methane; 4-Nitrophenyl chloroformate With triethylamine In dichloromethane at 20℃; for 48h; Inert atmosphere; Stage #2: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine With triethylamine In dichloromethane at 20℃; Inert atmosphere; | 76.8% |
4-Nitrophthalonitrile
bis-(4-hydroxyphenyl)methane
4,4'-Bis-(3,4-dicyanophenoxy)diphenylmethan
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 12h; Inert atmosphere; | 74.28% |
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 30℃; for 12h; |
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