Phenyl 4-hydroxybenzoate
4,4'-Dihydroxybenzophenone
Conditions | Yield |
---|---|
With aluminum (III) chloride In carbon disulfide for 6h; Concentration; Fries Phenol Ester Rearrangement; Reflux; | 97% |
Conditions | Yield |
---|---|
With 2-(diethylamino)ethanethiol hydrochloride; sodium t-butanolate In N,N-dimethyl-formamide for 2h; Heating; | 92% |
With potassium carbonate; 3-mercaptopropionic acid In ISOPROPYLAMIDE at 150℃; for 18h; | 89% |
Stage #1: bis(p-methoxyphenyl)methanone With potassium carbonate; 3-mercaptopropionic acid In ISOPROPYLAMIDE at 150℃; for 18h; Stage #2: With hydrogenchloride In water | 89% |
With aluminum tri-bromide; benzene |
carbon monoxide
(p-hydroxyphenyl)boronic acid
4,4'-Dihydroxybenzophenone
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; oxygen; copper(l) chloride In N,N-dimethyl-formamide at 80℃; for 24h; Schlenk technique; | 91% |
4,5-dichloro-1-phenylpyridazin-6-one
A
4,4'-Dihydroxybenzophenone
B
chloridazon
Conditions | Yield |
---|---|
In water | A n/a B 89.5% |
bis(4-hydroxyphenyl)methanol
4,4'-Dihydroxybenzophenone
Conditions | Yield |
---|---|
With C6H4MoNO7(1-)*C19H42N(1+); oxygen In water at 100℃; for 20h; Green chemistry; chemoselective reaction; | 79% |
Conditions | Yield |
---|---|
In cyclohexane | 70% |
In cyclohexane |
Conditions | Yield |
---|---|
With titanium(IV) oxide for 0.00694444h; Friedel Crafts acylation; Microwave irradiation; | 70% |
Conditions | Yield |
---|---|
With methanesulfonic acid In toluene at 120℃; for 12h; | 67% |
With PPA | |
With tin(IV) chloride |
2,2′‐[(carbonylbis(4,1‐phenylene))bis(oxy)]diacetic acid
4,4'-Dihydroxybenzophenone
Conditions | Yield |
---|---|
Stage #1: 2,2′‐[(carbonylbis(4,1‐phenylene))bis(oxy)]diacetic acid With triethylamine In N,N-dimethyl-formamide; toluene for 3h; Curtius rearrangement; Heating; Stage #2: With potassium hydroxide; glycerol In ethanol; N,N-dimethyl-formamide; toluene for 2h; Heating; Further stages.; | 51% |
A
4-hydroxy-1-ferrocenylbutan-1-one
B
4,4'-Dihydroxybenzophenone
Conditions | Yield |
---|---|
With silver(l) oxide In acetone at 20℃; for 0.166667h; | A n/a B 34% C 15% D 30% |
A
4-hydroxy-1-ferrocenylbutan-1-one
B
4,4'-Dihydroxybenzophenone
Conditions | Yield |
---|---|
Stage #1: 2-ferrocenyl-1,1-bis-(4-hydroxyphenyl)-5-hydroxy-pent-1-ene With silver(l) oxide In acetone Stage #2: With hydrogenchloride In acetone | A 25% B 23% C 10% D 28% E 1% F 18% G 18% |
4-hydroxy-4'-nitrobenzophenone
4,4'-Dihydroxybenzophenone
Conditions | Yield |
---|---|
aufeinanderfolgende Reduktion, Diazotierung und Verkochung der Diazoniumsalzloesung; |
Conditions | Yield |
---|---|
With aluminium trichloride at 140℃; |
Conditions | Yield |
---|---|
With sodium hydroxide; air |
Conditions | Yield |
---|---|
With water at 220 - 250℃; |
Conditions | Yield |
---|---|
With water at 270℃; |
Conditions | Yield |
---|---|
With cis-nitrous acid |
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
With water at 270℃; |
Conditions | Yield |
---|---|
bei der Kalischmelze; |
2-hydroxy-5-(4-hydroxy-benzoyl)-benzoic acid
4,4'-Dihydroxybenzophenone
Conditions | Yield |
---|---|
With quinoline; copper |
2,2'-dihydroxy-5,5'-carbonyl-di-isophthalic acid
4,4'-Dihydroxybenzophenone
Conditions | Yield |
---|---|
With quinoline |
phenyl Salicylate
A
4-[(2-hydroxyphenyl)carbonyl]phenol
B
4,4'-Dihydroxybenzophenone
Conditions | Yield |
---|---|
With tin(IV) chloride |
Conditions | Yield |
---|---|
With carbon disulfide; aluminium trichloride und Erhitzen des nach der Hydrolyse erhaltenen Reaktionsprodukts mit AlCl3 in Toluol auf 120grad; |
Conditions | Yield |
---|---|
With sodium hydroxide; water; copper(II) oxide at 150 - 250℃; im Kupfer-Autoklaven; |
salicylic acid
phenol
A
4-[(2-hydroxyphenyl)carbonyl]phenol
B
4,4'-Dihydroxybenzophenone
Conditions | Yield |
---|---|
With tin(IV) chloride |
tetrachloromethane
(E)-3-Ureido-but-2-enoic acid ethyl ester
phenol
A
bis(phenyl) carbonate
B
4-[(2-hydroxyphenyl)carbonyl]phenol
C
4,4'-Dihydroxybenzophenone
tetrachloromethane
phenol
A
4-[(2-hydroxyphenyl)carbonyl]phenol
B
4,4'-Dihydroxybenzophenone
Conditions | Yield |
---|---|
With zinc(II) chloride at 120℃; |
Conditions | Yield |
---|---|
With acetic acid at 160 - 170℃; |
Conditions | Yield |
---|---|
beim Schmelzen; |
4,4'-Dihydroxybenzophenone
benzyl chloride
4,4'-bis(benzyloxy)benzophenone
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 50℃; for 3.5h; | 100% |
With sodium hydroxide |
4-bromoethylbutanoate
4,4'-Dihydroxybenzophenone
4-{4-[4-(3-ethoxycarbonyl-propoxy)-benzoyl]-phenoxy}-butyric acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 12h; Heating; | 100% |
4,4'-Dihydroxybenzophenone
tert-butyldimethylsilyl chloride
bis(4-((tert-butyldimethylsilyl)oxy)phenyl)methanone
Conditions | Yield |
---|---|
With 1H-imidazole; dmap In dichloromethane; N,N-dimethyl-formamide for 3h; | 99% |
Stage #1: tert-butyldimethylsilyl chloride With 1H-imidazole In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 4,4'-Dihydroxybenzophenone In dichloromethane at 20℃; for 3h; Inert atmosphere; | 98% |
With 1H-imidazole In N,N-dimethyl-formamide for 3h; | 97% |
With 1H-imidazole In dichloromethane at 20℃; | 95% |
4,4'-Dihydroxybenzophenone
cycloheptanone
4,4'-(cycloheptylidenemethanediyl)diphenol
Conditions | Yield |
---|---|
With titanium tetrachloride; zinc In tetrahydrofuran at 20℃; for 3h; McMurry Reaction; Heating / reflux; | 99% |
With titanium tetrachloride; zinc In tetrahydrofuran at 20℃; for 3h; Heating / reflux; | 99% |
With titanium tetrachloride; zinc In tetrahydrofuran for 2h; McMurry coupling; Heating; | 83% |
4,4'-Dihydroxybenzophenone
ethyl bromoacetate
4,4’-bis(ethoxycarbonylmethoxy)benzophenone
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 18h; | 99% |
4,4'-Dihydroxybenzophenone
allyl bromide
bis(4-(allyloxy)phenyl)methanone
Conditions | Yield |
---|---|
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 24h; | 99% |
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 24h; | 99% |
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 24h; | 99% |
Stage #1: 4,4'-Dihydroxybenzophenone With potassium carbonate In acetone for 6h; Stage #2: allyl bromide In acetone for 24h; Reflux; | 75% |
With potassium carbonate In tetrahydrofuran; tetrachloromethane at 60℃; for 24h; Inert atmosphere; | 5.78 g |
Conditions | Yield |
---|---|
In ethanol at 20℃; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With triethylamine In benzene at 20 - 30℃; for 1h; Inert atmosphere; | 99% |
Stage #1: 4,4'-Dihydroxybenzophenone With triethylamine at 20 - 30℃; for 0.5h; Inert atmosphere; Stage #2: chlorophosphoric acid diphenyl ester at 20 - 30℃; for 1h; | |
Stage #1: 4,4'-Dihydroxybenzophenone With triethylamine In 5,5-dimethyl-1,3-cyclohexadiene for 0.5h; Inert atmosphere; Stage #2: chlorophosphoric acid diphenyl ester In 5,5-dimethyl-1,3-cyclohexadiene at 20 - 30℃; for 1h; | |
Stage #1: 4,4'-Dihydroxybenzophenone With triethylamine In 5,5-dimethyl-1,3-cyclohexadiene at 20 - 30℃; for 0.5h; Inert atmosphere; Stage #2: chlorophosphoric acid diphenyl ester In 5,5-dimethyl-1,3-cyclohexadiene at 20 - 30℃; for 1h; |
Conditions | Yield |
---|---|
Stage #1: 4,4'-Dihydroxybenzophenone With triethylamine In tetrahydrofuran at 0℃; for 0.333333h; Stage #2: Diphenylphosphinic chloride In tetrahydrofuran at 0 - 20℃; for 2h; | 99% |
4,4'-Dihydroxybenzophenone
ethylene dibromide
4,4’-bis(2-bromoethoxy)benzophenone
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate In acetone for 96h; Inert atmosphere; | 98% |
With potassium carbonate In acetone Reflux; | 87% |
With potassium carbonate In acetone for 24h; Reflux; | 70% |
4,4'-Dihydroxybenzophenone
Conditions | Yield |
---|---|
With fluorosulfonyl fluoride; triethylamine In dichloromethane at 20℃; for 12h; | 98% |
4,4'-Dihydroxybenzophenone
benzyl bromide
4,4'-bis(benzyloxy)benzophenone
Conditions | Yield |
---|---|
With potassium carbonate In methanol; chloroform for 48h; Heating; | 97% |
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 1h; | 96.9% |
With ethanol; sodium ethanolate |
1-bromo-hexane
4,4'-Dihydroxybenzophenone
4,4’-bis(hexylphenyl)benzophenone
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 48h; Williamson ether synthesis; Reflux; | 97% |
With tetrabutylammomium bromide; potassium carbonate In acetone for 48h; Concentration; Williamson Ether Synthesis; Reflux; | 92% |
With potassium carbonate In N,N-dimethyl-formamide for 48h; Reflux; | 75% |
With potassium carbonate In N,N-dimethyl-formamide Heating; |
4,4'-Dihydroxybenzophenone
1-bromo-3,7R,11R,15-tetramethylhexadecane
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 5h; | 97% |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 5h; | |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 5h; |
4,4'-Dihydroxybenzophenone
tert-butylchlorodiphenylsilane
Conditions | Yield |
---|---|
Stage #1: tert-butylchlorodiphenylsilane With 1H-imidazole In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 4,4'-Dihydroxybenzophenone In dichloromethane at 20℃; for 3h; Inert atmosphere; | 97% |
4,4'-Dihydroxybenzophenone
1-phenyl-propan-1-one
1,1-bis(4-hydroxyphenyl)-2-phenyl-1-butene
Conditions | Yield |
---|---|
With titanium tetrachloride; zinc In tetrahydrofuran at 0℃; for 2h; McMurry reaction; Inert atmosphere; Reflux; Darkness; | 96% |
With titanium tetrachloride; zinc In tetrahydrofuran McMurry Reaction; Inert atmosphere; | 94% |
With titanium tetrachloride; zinc In tetrahydrofuran for 2h; Heating; | 91% |
(S)-2-butanol
4,4'-Dihydroxybenzophenone
4,4’-bis[(R)-sec-butyloxy]benzophenone
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu coupling; | 96% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; toluene at 0 - 20℃; for 27.5h; Inert atmosphere; | 93% |
4,4'-Dihydroxybenzophenone
1-(3-bromophenyl)-1-propanone
4,4'-(2-(3-bromophenyl)-1-butene-1,1-diyl)diphenol
Conditions | Yield |
---|---|
Stage #1: 4,4'-Dihydroxybenzophenone; 1-(3-bromophenyl)-1-propanone In tetrahydrofuran at 20℃; for 3h; Heating / reflux; Stage #2: McMurry Reaction; | 96% |
4'-Bromopropiophenone
4,4'-Dihydroxybenzophenone
4,4'-[2-(4-bromophenyl)-1-butene-1,1-diyl]diphenol
Conditions | Yield |
---|---|
With zinc; titanium tetrachloride In tetrahydrofuran at 20℃; for 3h; McMurry Reaction; Heating / reflux; | 96% |
(Propionylcyclopentadienyl)tricarbonylmanganese
4,4'-Dihydroxybenzophenone
1,1-di(4-hydroxyphenyl)-2-cymantrenylbut-1-ene
Conditions | Yield |
---|---|
With titanium tetrachloride; zinc In tetrahydrofuran (Ar); using Schlenk techniques; addn. dropwise of TiCl4 to suspn. of Zn in THF at 0°C; reflux for 2 h; addn. dropwise soln. of 4,4'-dihydroxybenzophenone and (CO)3Mn(C5H4COC2H5) in THF; reflux for 2 h; cooling to room temp., stirring with H2O and CH2Cl2; treatment with diluted HCl; decanting, extn. of aq. layer with CH2Cl2; drying of combined org. layers over MgSO4, concn. under reduced pressure, chromy. on silica gel with CH2Cl2; elem. anal.; | 96% |
4,4'-Dihydroxybenzophenone
1,1-di(4-hydroxyphenyl)-2-ruthenocenylbut-1-ene
Conditions | Yield |
---|---|
With titanium tetrachloride; zinc In tetrahydrofuran (Ar); using Schlenk techniques; addn. dropwise of TiCl4 to suspn. of Zn in THF at 0°C; reflux for 2 h; addn. dropwise soln. of 4,4'-dihydroxybenzophenone and (C5H5)Ru(C5H4COC2H5) in THF; reflux for 2 h; cooling to room temp., stirring with H2O and CH2Cl2; treatment with diluted HCl; decanting, extn. of aq. layer with CH2Cl2; drying of combined org. layers over MgSO4, concn. under reduced pressure, chromy. on silica gel with CH2Cl2; elem. anal.; | 96% |
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; toluene at 0 - 20℃; for 17.5h; Inert atmosphere; | 96% |
4,4'-Dihydroxybenzophenone
4-[(4-chloro-2-pyrimidinyl)amino]benzonitrile
Conditions | Yield |
---|---|
Stage #1: 4,4'-Dihydroxybenzophenone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 4-[(4-chloro-2-pyrimidinyl)amino]benzonitrile In N,N-dimethyl-formamide at 80℃; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With titanium tetrachloride; zinc In tetrahydrofuran at 0 - 20℃; for 5h; McMurry Reaction; Inert atmosphere; Reflux; | 96% |
Conditions | Yield |
---|---|
With titanium tetrachloride; zinc In tetrahydrofuran at 0 - 20℃; for 5h; McMurry Reaction; Inert atmosphere; Reflux; | 96% |
With titanium tetrachloride; zinc In tetrahydrofuran for 2.5h; McMurry Reaction; Inert atmosphere; Reflux; | 70% |
With titanium tetrachloride; zinc In tetrahydrofuran McMurry Reaction; |
4,4'-Dihydroxybenzophenone
Conditions | Yield |
---|---|
With potassium carbonate In methanol Reflux; | 95.3% |
4,4'-Dihydroxybenzophenone
propargyl bromide
(4,4'-bis(prop-2-yn-1-yloxy))benzophenone
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 3h; Heating; | 95% |
With potassium carbonate In acetone for 24h; Heating; | 95% |
With potassium carbonate In acetone for 24h; Reflux; | 83% |
With potassium carbonate In acetone for 24h; Reflux; | 83% |
Stage #1: 4,4'-Dihydroxybenzophenone With potassium carbonate In acetone for 0.5h; Reflux; Stage #2: propargyl bromide for 20h; Reflux; | 72% |
Conditions | Yield |
---|---|
With titanium tetrachloride; zinc In tetrahydrofuran at 0 - 20℃; for 5h; McMurry Reaction; Inert atmosphere; Reflux; | 95% |
With titanium tetrachloride; zinc In tetrahydrofuran at -10 - 20℃; for 5.5h; McMurry Reaction; Heating / reflux; dark; | 89% |
With titanium tetrachloride; zinc In tetrahydrofuran for 2.5h; McMurry Reaction; Inert atmosphere; Reflux; | 89% |
With titanium tetrachloride; zinc In tetrahydrofuran at -10 - 0℃; for 2.5h; Inert atmosphere; Reflux; | 89% |
Conditions | Yield |
---|---|
With sodium hydroxide In N,N-dimethyl-formamide | 95% |
IUPAC Name: bis(4-hydroxyphenyl)methanone
Empirical Formula: C13H10O3
Molecular Weight: 214.2167g/mol
EINECS: 210-288-1
Structure of Methanone,bis(4-hydroxyphenyl)- (CAS NO.611-99-4):
Index of Refraction: 1.647
Molar Refractivity: 59.8 cm3
Molar Volume: 164.4 cm3
Polarizability: 23.71×10-24cm3
Surface Tension: 59.6 dyne/cm
Density: 1.302 g/cm3
Flash Point: 237 °C
Enthalpy of Vaporization: 72.98 kJ/mol
Melting Point: 213-215 °C(lit.)
Boiling Point: 444.8 °C at 760 mmHg
Vapour Pressure: 1.58E-08 mmHg at 25°C
Water Solubility: insoluble
Product Categories: Aromatic Benzophenones & Derivatives (substituted);Benzophenones (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;C13 to C14;Carbonyl Compounds;Ketones;AlcoholsPolymerization Initiators;Benzophenone;Monomers;Organic Photoinitiators;Polymer Science
Canonical SMILES: C1=CC(=CC=C1C(=O)C2=CC=C(C=C2)O)O
InChI: InChI=1S/C13H10O3/c14-11-5-1-9(2-6-11)13(16)10-3-7-12(15)8-4-10/h1-8,14-15H
InChIKey: RXNYJUSEXLAVNQ-UHFFFAOYSA-N
The main application of Methanone,bis(4-hydroxyphenyl)- is used as a UV light stabalizer. It is used extensively in cosmetics, plastics, films, adhesives and coatings, optical fiber, and printed circuit boards. Methanone,bis(4-hydroxyphenyl)- works by absorbing the Ultraviolet RADIATION and preventing the formation of free radicals.
Ph(CO2)Ph → (HOC6H4)2CO
The preparation method of 4,4`dihydroxybenzophenone includes rearranging Ph p-hydroxybenzoate in the presence of catalyst at a molar ratio of 1:(0.1-1) in organic solvent at 70-170?C for 3-20 h; separating; and recrystalizing. to obtain 4,4'-dihydroxybenzophenone, wherein Ph p-hydroxybenzoate is prepared. by acetylating p-hydroxybenzoic acid to generate p-acetoxybenzoic acid; chlorinating to generate p-acetoxybenzoyl chloride; and reacting with PHENOL and deacetylating to obtain Ph p-hydroxybenzoate.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD | intraperitoneal | > 500mg/kg (500mg/kg) | "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 4, Pg. 376, 1952. |
Hazard Codes: Xi
Risk Statements: 36/37/38-43
R36/37/38:Irritating to eyes, respiratory system and skin.
R43:May cause sensitization by skin contact.
Safety Statements: 26-36/37-37/39-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37:Wear suitable protective clothing and gloves.
S37/39:Wear suitable gloves and eye/face protection.
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: DJ0880000
HS Code: 29145000
Methanone,bis(4-hydroxyphenyl)- , its cas register number is 611-99-4. It also can be called 4,4'-Dihydroxybenzophenone
4,4'-Dihydroxydiphenyl ketone ; 4-08-00-02452 (Beilstein Handbook Reference) ; AI3-00127 ; Bis(4-hydroxyphenyl) ketone ; Bis(p-hydroxy)benzophenone ; HBP (ketone) ; NSC 2831 ; p,p'-Dihydroxybenzophenone . Methanone,bis(4-hydroxyphenyl)- (CAS NO.611-99-4) is a off-white to beige fine crystalline powder.
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