Conditions | Yield |
---|---|
With potassium tert-butylate; N,N-dimethyl-formamide at 35℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation; | 100% |
With tris-(trimethylsilyl)silane In acetonitrile for 24h; Schlenk technique; Inert atmosphere; Irradiation; | 98% |
With aluminium trichloride In dichloromethane; ethanethiol for 0.15h; Mechanism; Ambient temperature; var. other halogenated phenols; | 86.7% |
With potassium phosphate; palladium diacetate; hydrazine hydrate In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃; for 8h; Green chemistry; | 68% |
Conditions | Yield |
---|---|
montmorillonite K-10 for 0.0166667h; Product distribution; Further Variations:; Catalysts; Solid phase reaction; desilylation; microwave irradiation; | 100% |
With bismuth(lll) trifluoromethanesulfonate In methanol at 20℃; for 0.0333333h; | 98% |
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0666667h; Green chemistry; | 98% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine at 54℃; for 20h; Product distribution; Rate constant; Thermodynamic data; other solvents, reagents, reagents ratio, time, temperature; activation energy, ΔH<*>, ΔS<*>; | A 100% B n/a C 100% |
Conditions | Yield |
---|---|
With phosphate buffer; Phenyl acetate In diethyl ether for 2.75h; Ambient temperature; pig liver acetone powder; | A 5% B 100% |
phenyl-α-chloroethyl-carbonate
A
phenyl 1-thiocyanoethylcarbonate
B
phenol
Conditions | Yield |
---|---|
In formamide for 72h; Ambient temperature; | A 100% B 35% |
Conditions | Yield |
---|---|
With thallous phenoxide In diethyl ether for 24h; | A 100% B 94% |
Conditions | Yield |
---|---|
With aluminium(III) iodide; tetra-(n-butyl)ammonium iodide In cyclohexane for 0.3h; Heating; | 100% |
With water; hydrogen bromide; Aliquat 336 at 105℃; for 5h; Catalytic behavior; | 96% |
With monochloroborane dimethyl sulfide complex In benzene Heating; | 95% |
Conditions | Yield |
---|---|
With hydrogen; sodium hydroxide In water under 760.051 Torr; for 0.833333h; Kinetics; Reagent/catalyst; Solvent; Green chemistry; | 100% |
With hydrogen; sodium hydroxide In water at 20℃; for 2h; Kinetics; Catalytic behavior; Solvent; Reagent/catalyst; | 99.1% |
With hydrogen; sodium hydroxide In water at 25℃; under 760.051 Torr; for 2h; Reagent/catalyst; Solvent; | 99.9% |
7,7,8,8-Tetramethyl-3-methylene-5-phenoxy-1,4,6,9-tetraoxa-5λ5-phospha-spiro[4.4]nonan-2-one
A
2-hydroxy-4,4,5,5-tetramethyl<1,3,2>dioxaphospholane-2-oxide
B
2-oxo-propionic acid
C
phenol
Conditions | Yield |
---|---|
With water In acetone at 20℃; for 24h; | A 100% B n/a C n/a |
Conditions | Yield |
---|---|
With HZSM-5(30) In water for 7h; Product distribution; Heating; var. catalysts; other acetylated alcohols; | 100% |
silica gel; toluene-4-sulfonic acid In water; toluene at 80℃; for 6h; | 100% |
With sodium hydrogen telluride; acetic acid In ethanol for 0.5h; Heating; | 100% |
Conditions | Yield |
---|---|
With phosphate buffer; Phenyl acetate In diethyl ether for 2.75h; Ambient temperature; pig liver acetone powder; | A 18% B 100% |
Conditions | Yield |
---|---|
With phosphate buffer; Phenyl acetate In diethyl ether for 2.75h; Ambient temperature; pig liver acetone powder; | A 9% B 100% |
Conditions | Yield |
---|---|
With perchloric acid In diethyl ether; water at 20℃; for 0.166667h; | 100% |
With samarium diiodide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 0.0833333h; Etherification; | 99.3% |
With sodium hydroxide In water at 20℃; | 91% |
Conditions | Yield |
---|---|
H6P2W18O62; silica gel In tetrahydrofuran; methanol at 65℃; for 0.916667h; Product distribution; Further Variations:; Catalysts; | 100% |
With bismuth(III) chloride In water; acetonitrile at 50℃; for 1h; Reagent/catalyst; Solvent; Temperature; | 95% |
sodium hydrogen sulfate; silica gel In dichloromethane at 20℃; for 1.5h; | 94% |
bis(1,5-cyclooctadiene)nickel (0)
tetrakis(triphenylphosphine)nickel(0)
B
(triphenylphosphine)3(CO)nickelk
C
ethene
D
phenol
Conditions | Yield |
---|---|
With triphenylphosphine In neat (no solvent) (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and Ni(PPh3)4, mixture stirred at 54°C for 20 h; GLC; | A 73% B n/a C 100% D 91% |
bis(1,5-cyclooctadiene)nickel (0)
phenyl propionate
A
(triphenylphosphine)3(CO)nickelk
B
ethene
C
phenol
Conditions | Yield |
---|---|
With triphenylphosphine In neat (no solvent) Kinetics; byproducts: diethyl ketone, 1,3-cyclooctadiene, 1,4-cyclooctadiene; further byproducts: 1,5-cyclooctadiene, bicyclooctene-1, bicyclooctene-2, (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and PPh3 (PPh3/Ni = 10), mixture stirred at 54°C for 21 h; gas chromy., volatile removed in vac., recrystd. from THF-hexane; | A 80% B 100% C 100% |
With triphenylphosphine In neat (no solvent) Kinetics; byproducts: diethyl ketone, 1,3-cyclooctadiene, 1,4-cyclooctadiene; further byproducts: 1,5-cyclooctadiene, bicyclooctene-1, bicyclooctene-2, (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and PPh3 (PPh3/Ni = 4),mixture stirred at 54°C for 20 h; gas chromy., volatile removed in vac., recrystd. from THF-hexane; | A 60% B 100% C 100% |
With triphenylphosphine In neat (no solvent) Kinetics; byproducts: diethyl ketone, 1,3-cyclooctadiene, 1,4-cyclooctadiene; further byproducts: 1,5-cyclooctadiene, bicyclooctene-1, bicyclooctene-2, (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and PPh3 (PPh3/Ni = 3),mixture stirred at 54°C for 20 h; gas chromy., volatile removed in vac., recrystd. from THF-hexane; | A 60% B 90% C 90% |
With triphenylphosphine In neat (no solvent) Kinetics; byproducts: diethyl ketone, 1,3-cyclooctadiene, 1,4-cyclooctadiene; further byproducts: 1,5-cyclooctadiene, bicyclooctene-1, bicyclooctene-2, (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and PPh3 (PPh3/Ni = 2),mixture stirred at 54°C for 12 h; gas chromy., volatile removed in vac., recrystd. from THF-hexane; | A 30% B 60% C 60% |
With triphenylphosphine In neat (no solvent) Kinetics; byproducts: diethyl ketone, 1,3-cyclooctadiene, 1,4-cyclooctadiene; further byproducts: 1,5-cyclooctadiene, bicyclooctene-1, bicyclooctene-2, (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and PPh3 (PPh3/Ni = 1),mixture stirred at 54°C for 12 h; gas chromy., volatile removed in vac., recrystd. from THF-hexane; | A n/a B 40% C 50% |
bis(1,5-cyclooctadiene)nickel (0)
phenyl propionate
Tri(p-tolyl)phosphine
A
ethene
B
Ni(CO)(P(C6H4CH3)3)3
C
phenol
Conditions | Yield |
---|---|
In further solvent(s) Kinetics; (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and P(C6H4CH3)3 (P(Ph-CH3)3/Ni = 3) in acetophenone, mixture stirred at 65°C for 50 h; | A 80% B 85% C 100% |
Conditions | Yield |
---|---|
With aluminum (III) chloride; diphenyl diselenide; zinc In acetonitrile at 70℃; for 19.25h; | 100% |
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
phenol
Conditions | Yield |
---|---|
With urea hydrogen peroxide adduct In methanol at 27 - 29℃; for 0.25h; Green chemistry; chemoselective reaction; | 100% |
With dihydrogen peroxide; 1-butyl-3-methylimidazolium chloride In water at 20℃; for 0.5h; Green chemistry; | 97% |
With water; 3-chloro-benzenecarboperoxoic acid In ethanol at 20℃; for 6h; | 96% |
phenol
Conditions | Yield |
---|---|
With urea hydrogen peroxide adduct In methanol at 27 - 29℃; for 0.25h; Green chemistry; chemoselective reaction; | 100% |
With Oxone; water In acetone at 20℃; for 0.0333333h; | 96% |
With LACTIC ACID; dihydrogen peroxide In water at 20℃; for 0.166667h; Green chemistry; | 89% |
Conditions | Yield |
---|---|
With C5H11N*Cu(2+)*2NO3(1-); water at 30℃; for 2h; | 100% |
With water at 60℃; for 5h; Green chemistry; | 100% |
With water; oxygen; sodium sulfite at 50℃; for 1h; Temperature; Green chemistry; | 100% |
phenyl 3,3-dimethylacrylate
phenol
Conditions | Yield |
---|---|
With perchloric acid In acetonitrile at 20℃; for 1.25h; photo-Fries rearrangement; Inert atmosphere; Irradiation; | 100% |
phenyl methanesulfonate
phenol
Conditions | Yield |
---|---|
With sodium phosphate In aq. phosphate buffer; water; dimethyl sulfoxide at 25℃; for 0.333333h; pH=7.5; Enzymatic reaction; | 100% |
2-hydroxyphenyl boronic acid
phenol
Conditions | Yield |
---|---|
In dimethylsulfoxide-d6 at 120℃; for 2h; Suzuki Coupling; Inert atmosphere; | 100% |
In dimethyl sulfoxide at 120℃; for 4h; Solvent; Temperature; | 100% |
In dimethyl sulfoxide at 120℃; for 4h; Solvent; Temperature; Time; Reagent/catalyst; | 95% |
With N-methyliminodiacetic acid In dimethyl sulfoxide; toluene at 120℃; for 12h; Inert atmosphere; Molecular sieve; | |
With 3-methyl-5H-1,4,2-dioxazol-5-one; Cp*Rh(OAc)2*H2O In tetrahydrofuran at 20℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; |
phenol
Conditions | Yield |
---|---|
With water In dimethyl sulfoxide at 120℃; for 24h; Time; Reagent/catalyst; | 100% |
In dimethyl sulfoxide at 120℃; for 12h; | 96% |
Multi-step reaction with 2 steps 1: dimethyl sulfoxide; toluene / 12 h / Molecular sieve; Reflux; Dean-Stark 2: dimethyl sulfoxide / 240 h / 120 °C View Scheme |
2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
phenol
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 120℃; for 24h; | 100% |
In dimethyl sulfoxide at 120℃; for 24h; | 96% |
(p-hydroxyphenyl)boronic acid
phenol
Conditions | Yield |
---|---|
With acetic acid In 1,4-dioxane at 100℃; Reagent/catalyst; Solvent; Enzymatic reaction; | 100% |
In formic acid at 60℃; for 2h; | 82% |
With acetic acid at 130℃; for 1h; Reagent/catalyst; Temperature; Green chemistry; | 81% |
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In toluene at 70℃; for 1.5h; Temperature; Microwave irradiation; Green chemistry; | 65% |
Conditions | Yield |
---|---|
With boron tribromide In dichloromethane | 100% |
Conditions | Yield |
---|---|
With Ni0.85Rh0.15; hydrogen In water at 95℃; under 760.051 Torr; for 16h; Reagent/catalyst; | A 100% B 5% C 79% |
With isopropyl alcohol at 150℃; under 7500.75 Torr; for 48h; Inert atmosphere; Autoclave; | A 100% B 12.2% C 87.5% |
With isopropyl alcohol at 150℃; under 7500.75 Torr; for 3h; Catalytic behavior; Temperature; Inert atmosphere; Autoclave; | A 100% B 73.1% C 22.4% |
With Ru0.6Ni0.4; hydrogen In water at 95℃; under 760.051 Torr; for 16h; Reagent/catalyst; | A 98% B 61% C 6% |
With hydrogen In n-heptane at 140℃; under 750.075 Torr; for 6h; Catalytic behavior; | A 34 %Chromat. B 12 %Chromat. C 22 %Chromat. |
Conditions | Yield |
---|---|
With cerium(III) chloride; sodium iodide at 25℃; for 26h; | 100% |
With poly-p-styryl-acetonyltriphenylphosphonium bromide In dichloromethane at 20℃; for 3h; | 99% |
With zirconium(IV) chloride In dichloromethane for 1h; | 99% |
Conditions | Yield |
---|---|
With copper; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 0.166667h; Ullmann Condensation; Microwave irradiation; Inert atmosphere; | 100% |
With 1,1,1,5,5,5-hexafluoroacetylacetone; copper(II) ferrite; caesium carbonate In 1-methyl-pyrrolidin-2-one at 135℃; for 24h; Ullmann Condensation; Inert atmosphere; Schlenk technique; | 99% |
With 2-acetonylpyridine; caesium carbonate; copper(I) bromide In dimethyl sulfoxide at 90℃; for 15h; Inert atmosphere; chemoselective reaction; | 98% |
Conditions | Yield |
---|---|
With erbium(III) triflate In diethyl ether at 25℃; for 24h; | 100% |
With BiCl6(3-)*2C4H10N2*ClH*3H(1+)*H2O In neat (no solvent) at 20℃; for 0.166667h; | 90% |
With toluene-4-sulfonic acid; toluene Trennung von (+-)-1-Phenoxy-1-phenyl-aethanol-(2) und (+-)-2-Phenoxy-1-phenyl-aethanol-(1) ueber die 2-Carboxy-benzoyl-Derivate; | |
In benzene | |
Stage #1: phenol With sodium hydroxide In water at 80℃; for 0.166667h; Stage #2: styrene oxide In water at 100℃; for 3h; Reagent/catalyst; | 15.0 g |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20℃; | 100% |
With sodium hydride In tetrahydrofuran at 20℃; | 99% |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; | 97% |
Conditions | Yield |
---|---|
With pyridine In toluene at 220℃; for 24h; | 100% |
With pyridine | 97% |
With pyridine In toluene at 20 - 100℃; for 1h; | 65.2% |
Conditions | Yield |
---|---|
With pyridine; aluminum oxide at 103 - 105℃; for 2h; microwave irradiation; | 100% |
With 2,6-di-tert-butyl-pyridine; sodium tetracarbonyl cobaltate In acetonitrile for 12h; | 100% |
With SBA-15-Ph-Pr-SO3H at 20℃; for 0.25h; | 100% |
Conditions | Yield |
---|---|
With tetrabutyl-ammonium chloride; sodium hydroxide In dichloromethane; water at 0℃; for 0.0833333h; | 100% |
zinc(II) chloride In toluene | 99% |
With sodium hydride In tetrahydrofuran at 20℃; for 1h; | 98% |
Conditions | Yield |
---|---|
at 20℃; for 2h; | 100% |
With cesium fluoride | 93.1% |
With triethylamine In acetonitrile for 24.5h; Esterification; | 89% |
Conditions | Yield |
---|---|
With triethylamine In benzene at 10℃; Kinetics; Mechanism; Thermodynamic data; Various temperatures, various concentrations. E(act.), ΔS(act.); | 100% |
With triethylamine In dichloromethane at -15℃; for 1h; Green chemistry; | 100% |
With triethylamine In ethyl acetate at 0 - 20℃; for 0.166667h; Green chemistry; | 97% |
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 20℃; for 12h; Inert atmosphere; | 100% |
With dmap In dichloromethane at 20℃; for 3h; Inert atmosphere; | 99% |
dmap In dichloromethane at 20℃; for 2h; | 81% |
With diethyl ether; triethylamine |
Conditions | Yield |
---|---|
With cesium fluoride/clinoptilolite In dimethyl sulfoxide at 110℃; for 0.15h; Reagent/catalyst; Solvent; Temperature; Ullmann Condensation; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 17h; | 100% |
With potassium fluoride on basic alumina; 18-crown-6 ether In acetonitrile for 1h; Heating; | 98% |
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 2h; Green chemistry; | 100% |
With potassium carbonate for 0.05h; microwave irradiation; | 99% |
With sodium carbonate In water at 20℃; for 3h; Catalytic behavior; Reagent/catalyst; | 99% |
Conditions | Yield |
---|---|
With hydrogenchloride at 15 - 20℃; for 3h; | 100% |
With hydrogenchloride |
Conditions | Yield |
---|---|
With tetrabutyl-ammonium chloride; sodium hydroxide In dichloromethane; water at 0℃; for 0.0833333h; | 100% |
Conditions | Yield |
---|---|
Stage #1: phenol With sodium hydroxide In water at 25℃; for 0.666667h; Stage #2: epichlorohydrin In water at 30 - 35℃; for 16h; | 100% |
With n-Bu4NOSO2OCH2CHOHCH3; potassium carbonate at 75 - 80℃; for 1.5h; | 91% |
With n-BuNOSO2OCH2CHOHCH3; potassium carbonate at 75 - 80℃; for 1.5h; other aryl alcohols, var. phase transfer catalysts, var. reaction time; | 91% |
Conditions | Yield |
---|---|
With potassium hydroxide; acyclic polyethylene oxides In dichloromethane; water for 0.5h; | 100% |
With aluminum oxide; potassium fluoride In N,N-dimethyl-formamide for 1h; Product distribution; Ambient temperature; other phenols and alcohols, other alkylating agents, other reagents and solvents, var. time; | 100% |
With potassium hydroxide; Aliquat 336 at 20℃; for 5h; | 99% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 23℃; for 2h; Inert atmosphere; | 100% |
With dmap In tetrahydrofuran at 60℃; for 24h; | 94% |
With dmap In tetrahydrofuran Heating; | 94% |
With aluminium trichloride |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; | 100% |
Stage #1: phenylacetic acid With phosphoric acid; trifluoroacetic anhydride In acetonitrile at 25℃; for 0.5h; Stage #2: phenol In acetonitrile at 25℃; for 20h; | 93% |
Stage #1: phenylacetic acid With (E)-ethyl 2-cyano-2-(2-nitrophenylsulfonyloxyimino)acetate; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; Stage #2: phenol In dichloromethane at 25℃; | 87% |
Conditions | Yield |
---|---|
at 170℃; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h; Williamson Ether Synthesis; Darkness; Inert atmosphere; | 97% |
With sodium hydroxide In N-methyl-acetamide; water | 75% |
Conditions | Yield |
---|---|
With ethylaluminum dichloride bis(2-chloroethyl) ether complex In hexane; Cyclohexane-d12 at 25℃; for 2.5h; Catalytic behavior; Friedel-Crafts Alkylation; Glovebox; Inert atmosphere; regioselective reaction; | 100% |
bei Siedetemperatur; | |
at 75℃; unter Druck; |
Conditions | Yield |
---|---|
With Hexamethylphosphorous triamide In toluene at 130℃; for 8h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction; | 100% |
With phosphorus trichloride at 35 - 160℃; under 7.50075 Torr; for 6h; Temperature; Flow reactor; Inert atmosphere; | 94% |
With 1H-imidazole; carbon disulfide; Hexamethylphosphorous triamide In benzene at 20 - 25℃; for 24h; | 86% |
Conditions | Yield |
---|---|
With benzyltriphenylphosphonium peroxodisulfate; potassium bromide In acetonitrile for 4.5h; Heating; | 100% |
With sulfuric acid; C20H22Br2N2O5V; dihydrogen peroxide In methanol; water at 20℃; for 1.33333h; Catalytic behavior; | 100% |
With oxygen; sodium bromide In dibutyl ether at 45℃; under 760.051 Torr; for 5h; Schlenk technique; | 99% |
phenol
(4-hydroxyphenyl)tellurium trichloride
Conditions | Yield |
---|---|
With tellurium tetrachloride In tetrachloromethane for 3h; Substitution; Heating; | 100% |
With tetrachloromethane; tellurium tetrachloride | |
With tellurium tetrachloride |
Conditions | Yield |
---|---|
With potassium hydride In tetrahydrofuran at 70℃; Inert atmosphere; | 100% |
With potassium hydroxide In water at 24℃; for 0.5h; | 98% |
With potassium hydroxide In water for 0.25h; | 98% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; MgAlZr0.1-HT In Petroleum ether at 79.9℃; for 8h; | 100% |
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In methanol; chloroform at -25℃; for 0.333333h; | 97% |
With tert.-butylhydroperoxide In water; acetonitrile at 70℃; for 6h; Catalytic behavior; Temperature; Solvent; | 89% |
Conditions | Yield |
---|---|
With CuCl2 In acetonitrile | 100% |
With [CuII2(μ-OH)(1,2-bis(2-(bis(2-pyridylmethyl)aminomethyl)-6-pyridyl)ethane)](ClO4)3 ; dihydrogen peroxide; triethylamine In water; acetonitrile at 50℃; for 10h; Catalytic behavior; Inert atmosphere; | 99% |
With manganese(IV) oxide; sulfuric acid; aniline at 10℃; for 1.5h; | 95% |
Conditions | Yield |
---|---|
With hydrogen; tetra(n-butyl)ammonium hydrogensulfate; rhodium colloidal catalyst In water at 36℃; under 180018 Torr; for 62h; pH=7.5; Catalytic hydrogenation; | 100% |
In methanol; water | 100% |
With hydrogen In water at 70℃; under 7500.75 Torr; for 0.25h; | 100% |
Conditions | Yield |
---|---|
Stage #1: 4-nitro-aniline With hydrogenchloride; sodium nitrite In water at 2℃; for 1.5h; Stage #2: phenol With sodium hydroxide In water at 2 - 20℃; for 4h; | 100% |
Stage #1: 4-nitro-aniline With carboxyl- and nitrite- functionalized graphene quantum dots at 20℃; for 0.0833333h; Stage #2: phenol In water at 20℃; for 0.166667h; | 96% |
Stage #1: 4-nitro-aniline With hydrogenchloride In water; acetone at 0℃; Inert atmosphere; Stage #2: With sodium nitrite In water; acetone at 0℃; for 1h; Inert atmosphere; Stage #3: phenol With sodium carbonate; sodium hydroxide In water; acetone at 0 - 20℃; for 3h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
100% | |
With dimethylmonochlorosilane; triethylamine for 1h; temp.: below 40 deg C; | 57% |
With dimethylmonochlorosilane Heating; | |
at 20 - 160℃; for 2h; Inert atmosphere; |
Conditions | Yield |
---|---|
With dmap; trimethylsilylethoxyacetylene; mercury(II) oxide In 1,2-dichloro-ethane at 40℃; for 0.5h; | 100% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; | 100% |
With dmap; di-2-thienyl carbonate In dichloromethane at 20℃; for 2h; | 95% |
NCI Carcinogenesis Bioassay (oral); No Evidence: mouse, rat NCITR* National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-203 ,1980. . EPA Extremely Hazardous Substances List. Community Right-To-Know List. Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
OSHA PEL: TWA 5 ppm (skin)
ACGIH TLV: TWA 5 ppm (skin); BEI: 250 mg(total phenol)/g creatinine in urine at end of shift; Not Classifiable as a Human Carcinogen
DFG MAK: Confirmed Animal Carcinogen with Unknown Relevance to Humans; BAT: 300 mg/L at end of shift
NIOSH REL: (Phenol) TWA 20 mg/m3; CL 60 mg/m3/15M
DOT Classification: 6.1; Label: Poison
For occupational chemical analysis use OSHA: #32 or NIOSH: Phenol, 3502; Phenol and p-Cresol in Urine, 8305.
The Phenol, monohydroxy derivative of benzene, is an organic compound with the chemical formula C6H5OH. It has the EINECS register number 203-632-7 and CAS register number 108-95-2. Phenol is appreciably soluble in water, with about 8.3 g dissolving in 100 mL (0.88 M). In addition, Phenol is a colourless crystals with a characteristic odour. It is stable which should be protected from strong oxidizing agents, strong bases, strong acids, alkalies and calcium hypochlorite. Phenol is flammable which may discolour in light.
Physical properties about Phenol are: (1)ACD/LogP: 1.54; (2)ACD/LogD (pH 5.5): 1.54; (3)ACD/LogD (pH 7.4): 1.54; (4)ACD/BCF (pH 5.5): 8.72; (5)ACD/BCF (pH 7.4): 8.69; (6)ACD/KOC (pH 5.5): 164.00; (7)ACD/KOC (pH 7.4): 163.44; (8)#H bond acceptors: 1; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.553; (12)Molar Refractivity: 28.134 cm3; (13)Molar Volume: 87.863 cm3; (14)Polarizability: 11.153 10-24cm3; (15)Surface Tension: 40.9669990539551 dyne/cm; (16)Density: 1.071 g/cm3; (17)Flash Point: 72.475 °C; (18)Enthalpy of Vaporization: 43.524 kJ/mol; (19)Boiling Point: 181.839 °C at 760 mmHg; (20)Vapour Pressure: 0.614000022411346 mmHg at 25°C
Preparation of Phenol: Phenol has been made, over the years, by a variety of processes. Historically, an important method was the sulfonation of benzene followed by desulfonation with caustic soda:
C6H6 + H2SO4 → C6H5SO3H + H2O
C6H5SO3H + 2 NaOH → C6H5OH + Na2SO4
The above route to Phenol has no longer used. The principal process in use is the peroxidation of cumene (iso-propylbenzene) at 130 °C in the presence of air and a catalyst followed by decomposition of the peroxide at 55 to 65 °C in the presence of sulfuric acid. In the cumene process, cumene is oxidized to form cumene hydroperoxide that is then concentrated and cleaved to produce phenol and acetone. By-products of the oxidation reaction are acetophenone and dimethyl benzyl alcohol, which is dehydrated in the cleavage reaction to produce alpha-methylstyrene.
C6H6 + CH2=CH-CH3 → C6H5CH(CH3)2
C6H5CH(CH3)2 + O2 → C6H5C(CH3)2OOH
C6H5C(CH3)2OOH [H2SO4]→ C6H5OH + CH3COCH3
The toluene-benzoic acid process of preparation of Phenol involves three chemical reactions: (l) oxidation of toluene to form benzoic acid, (2) oxidation of benzoic acid to form phenyl benzoate, (3) hydrolysis of phenyl benzoate to form phenol.
2 C6H5CH3 + 3 O2 → 2 C3H5CO2H + 2 H2O
4 C6H5CO2H + O2 → 2 C6H5CO2C6H5 + 2 H2O + 2 CO2
C6H5CO2C6H5 + 2 OH- → 2 C6H5OH + CO2
Uses of Phenol: Phenol was widely used as an antiseptic, especially as Carbolic soap. Phenol is also used in the preparation of cosmetics including sunscreens, hair dyes, and skin lightening preparations. The major uses of Phenol involve its conversion to plastics or related materials. Condensation with acetone gives bisphenol-A. Phenol is also used as an oral anesthetic/analgesic, commonly used to temporarily treat pharyngitis. Phenol is also a versatile precursor to a large collection of drugs, most notably aspirin but also many herbicides and pharmaceuticals. Phenol is one of the chemicals for embalming bodies for study because of its ability to preserve tissues for extended periods of time.
When you are using Phenol, please be cautious about it. Phenol is toxic, harmful, corrosive and highly flammable. There will be a danger of serious damage to health by prolonged exposure through inhalation, and in contact with skin and if swallowed. In addition, Phenol is toxic by inhalation, in contact with skin and if swallowed. What's more, there is a danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact Phenol, you should wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you can seek medical advice immediately (show label where possible). Meanwhile, you must avoid contact with skin and eyes.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=C(C=C1)O
(2)InChI: InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
(3)InChIKey: ISWSIDIOOBJBQZ-UHFFFAOYSA-N
Toxicity of Phenol:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LDLo | oral | 80mg/kg (80mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1319, 1935. | |
cat | LDLo | subcutaneous | 80mg/kg (80mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 80, Pg. 233, 1944. | |
cat | LDLo | unreported | 250mg/kg (250mg/kg) | Revue Medicale de la Suisse Romande. Vol. 15, Pg. 561, 1895. | |
dog | LDLo | oral | 500mg/kg (500mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1319, 1935. | |
dog | LDLo | unreported | 200mg/kg (200mg/kg) | Revue Medicale de la Suisse Romande. Vol. 15, Pg. 561, 1895. | |
frog | LDLo | parenteral | 290mg/kg (290mg/kg) | PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: OTHER CHANGES | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 166, Pg. 437, 1932. |
frog | LDLo | subcutaneous | 75mg/kg (75mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1319, 1935. | |
frog | LDLo | subcutaneous | 290mg/kg (290mg/kg) | "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 228, 1955. | |
guinea pig | LDLo | intraperitoneal | 300mg/kg (300mg/kg) | "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 228, 1955. | |
guinea pig | LDLo | subcutaneous | 450mg/kg (450mg/kg) | "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 228, 1955. | |
human | LDLo | oral | 140mg/kg (140mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" SKIN AND APPENDAGES (SKIN): SWEATING: OTHER | "Practical Toxicology of Plastics," Lefaux, R., Cleveland, OH, Chemical Rubber Co., 1968Vol. -, Pg. 329, 1968. |
human | LDLo | oral | 14gm/kg (14000mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: CYANOSIS | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 463, 1969. |
infant | LDLo | oral | 10mg/kg (10mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: CYANOSIS | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 463, 1969. |
mammal (species unspecified) | LD50 | oral | 500mg/kg (500mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988. | |
man | TDLo | unreported | 5714ug/kg (5.714mg/kg) | SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION | Veterinary and Human Toxicology. Vol. 41, Pg. 151, 1999. |
mouse | LC50 | inhalation | 177mg/m3 (177mg/m3) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 41(6), Pg. 103, 1976. | |
mouse | LD50 | intraperitoneal | 180mg/kg (180mg/kg) | Pharmacologist. Vol. 10, Pg. 172, 1968. | |
mouse | LD50 | intravenous | 112mg/kg (112mg/kg) | BEHAVIORAL: TREMOR | Quarterly Journal of Pharmacy & Pharmacology. Vol. 12, Pg. 212, 1939. |
mouse | LD50 | oral | 270mg/kg (270mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 38(8), Pg. 6, 1973. | |
mouse | LD50 | subcutaneous | 344mg/kg (344mg/kg) | Industrial Health. Vol. 5, Pg. 143, 1967. | |
rabbit | LD50 | skin | 630mg/kg (630mg/kg) | Union Carbide Data Sheet. Vol. 1/6/1966, | |
rabbit | LDLo | intraperitoneal | 620mg/kg (620mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 80, Pg. 233, 1944. | |
rabbit | LDLo | intravenous | 180mg/kg (180mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 80, Pg. 233, 1944. | |
rabbit | LDLo | oral | 420mg/kg (420mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 80, Pg. 233, 1944. | |
rabbit | LDLo | subcutaneous | 620mg/kg (620mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 80, Pg. 233, 1944. | |
rabbit | LDLo | unreported | 150mg/kg (150mg/kg) | Revue Medicale de la Suisse Romande. Vol. 15, Pg. 561, 1895. | |
rat | LC50 | inhalation | 316mg/m3 (316mg/m3) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 41(6), Pg. 103, 1976. | |
rat | LD50 | intraperitoneal | 127mg/kg (127mg/kg) | Food and Chemical Toxicology. Vol. 22, Pg. 665, 1984. | |
rat | LD50 | oral | 317mg/kg (317mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Proceedings of the Society for Experimental Biology and Medicine. Vol. 32, Pg. 592, 1935. |
rat | LD50 | skin | 669mg/kg (669mg/kg) | BEHAVIORAL: TREMOR KIDNEY, URETER, AND BLADDER: HEMATURIA SKIN AND APPENDAGES (SKIN): CUTANEOUS SENSITIZATION (EXPERIMENTAL): AFTER TOPICAL EXPOSURE | British Journal of Industrial Medicine. Vol. 27, Pg. 155, 1970. |
rat | LD50 | subcutaneous | 460mg/kg (460mg/kg) | Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 10, Pg. 1, 1963. |
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