Conditions | Yield |
---|---|
100% | |
Stage #1: biphenyl-4-carboxylic acid With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 20℃; for 4h; Cooling with ice; Inert atmosphere; Stage #2: With water In tetrahydrofuran; diethyl ether for 16h; | 99% |
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
Stage #1: 4-Phenylbenzaldehyde With zinc diacetate In tetrahydrofuran at 65℃; for 0.166667h; Stage #2: With methyl-di(n-propoxy)silane In tetrahydrofuran at 65℃; for 24h; Stage #3: With hydrogenchloride; water at 0℃; for 1h; | 99% |
With iron(II) fluoro{tris[2-(diphenylphosphino)phenyl]phospino}tetrafluoroborate; hydrogen; trifluoroacetic acid In isopropyl alcohol at 120℃; under 15001.5 Torr; for 2h; Inert atmosphere; Autoclave; chemoselective reaction; | 99% |
With C46H49CoN3P4(2+)*2BF4(1-); hydrogen; potassium hydroxide In ethanol; acetonitrile at 60℃; under 22801.5 Torr; for 24h; Autoclave; Glovebox; chemoselective reaction; | 99% |
Conditions | Yield |
---|---|
With C20H20N2O2Pd; sodium hydrogencarbonate In water at 80℃; for 6h; Suzuki-Miyaura Coupling; | 99% |
With trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); potassium carbonate In water for 0.5h; Catalytic behavior; Suzuki-Miyaura Coupling; Sealed tube; Inert atmosphere; Reflux; | 98% |
With palladium diacetate; potassium carbonate In water; isopropyl alcohol at 20℃; for 0.25h; Suzuki-Miyaura Coupling; | 98% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 98% |
With hydrogenchloride In water; acetone for 1.5h; pH=12; | 24% |
With lithium aluminium tetrahydride | |
With diisobutylaluminium hydride In dichloromethane; toluene at -78℃; | |
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; |
Conditions | Yield |
---|---|
With sodium carbonate at 80℃; for 1.16667h; Catalytic behavior; Suzuki Coupling; | 98% |
With potassium carbonate for 4.25h; Suzuki-Miyaura Coupling; | 92% |
With potassium carbonate at 100℃; for 5.25h; Catalytic behavior; | 90% |
Conditions | Yield |
---|---|
With sodium hydroxide; aluminum oxide; ruthenium In 1,2-dimethoxyethane; water at 90℃; for 12h; Suzuki-Miyaura-type cross coupling reaction; | 97% |
With sodium t-butanolate In water at 28℃; for 4h; Catalytic behavior; Suzuki-Miyaura Coupling; Irradiation; | 96% |
With potassium carbonate In ethanol at 20℃; for 6h; Suzuki-Miyaura Coupling; | 91% |
p-hydroxymethylphenylboronic acid
chlorobenzene
biphenyl-4-yl methanol
Conditions | Yield |
---|---|
With C37H44ClN2O3PPd; caesium carbonate In water at 100℃; for 12h; Suzuki Coupling; Schlenk technique; Inert atmosphere; | 97% |
With potassium carbonate In water at 70℃; for 12h; Catalytic behavior; Temperature; Reagent/catalyst; Suzuki Coupling; Green chemistry; | 5 %Chromat. |
Conditions | Yield |
---|---|
With potassium carbonate for 4h; Stille Cross Coupling; | 96% |
With potassium carbonate at 100℃; for 5.5h; Catalytic behavior; Stille Cross Coupling; | 93% |
Conditions | Yield |
---|---|
With [PdCl[(η5-C5H5)]Fe[(η5-C5H3)-C(CH3)=NOH](2-dicyclohexylphosphanyl-2'-(N,N-dimethylamino)biphenyl)]; caesium carbonate In water at 100℃; for 24h; Catalytic behavior; Reagent/catalyst; Concentration; Suzuki Coupling; Schlenk technique; Inert atmosphere; | 92% |
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 5h; Catalytic behavior; Suzuki-Miyaura Coupling; | 88% |
With C20H16Cl2N2Pd; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Suzuki-Miyaura Coupling; | 83% |
Conditions | Yield |
---|---|
With potassium tert-butylate; C44H47I3IrN4PPd In tetrahydrofuran; isopropyl alcohol at 90℃; for 9h; Reagent/catalyst; Inert atmosphere; Schlenk technique; | 92% |
With C31H37I3IrN5Pd; potassium tert-butylate; isopropyl alcohol In tetrahydrofuran at 90℃; for 2h; Reagent/catalyst; Inert atmosphere; Schlenk technique; | 85% |
Conditions | Yield |
---|---|
With water; sodium formate; sodium carbonate at 100 - 105℃; for 1h; pH=7 - 7.5; Reagent/catalyst; | 91% |
With water at 100℃; for 24h; | 52% |
With water In N,N-dimethyl-formamide at 80℃; under 2250.23 Torr; for 20h; Temperature; Sealed tube; |
N, N-dimethyl [1,1’-biphenyl]-4-carboxamide
biphenyl-4-yl methanol
Conditions | Yield |
---|---|
With sodium hydride; sodium iodide; zinc(II) iodide In tetrahydrofuran; mineral oil at 40℃; for 10h; Sealed tube; | 89% |
Conditions | Yield |
---|---|
With potassium carbonate In methanol; water at 40 - 45℃; for 4h; Suzuki Coupling; | 88% |
With palladium diacetate; potassium carbonate In 2-methoxy-ethanol; water at 21℃; for 0.5h; Suzuki coupling; | > 99 %Chromat. |
With potassium phosphate In ethanol; water at 80℃; for 2h; Solvent; Reagent/catalyst; Time; Temperature; Suzuki-Miyaura Coupling; | |
With potassium carbonate In water at 70℃; for 12h; Catalytic behavior; Temperature; Reagent/catalyst; Suzuki Coupling; Green chemistry; | 75 %Chromat. |
4-methoxyphenylboronic acid
benzenediazonium tetrafluoroborate
biphenyl-4-yl methanol
Conditions | Yield |
---|---|
polystyrene-supported N-heterocyclic carbene-Pd complex In ethanol at 20℃; for 10h; Suzuki-Miyaura cross-coupling; | 87% |
4-bromo-1,1'-biphenyl
2-bromomethoxy-tetrahydro-pyran
biphenyl-4-yl methanol
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1,1'-biphenyl With n-Butyl chloride; iodine; magnesium In 2-methyltetrahydrofuran at 60℃; for 2h; Inert atmosphere; Reflux; Stage #2: 2-bromomethoxy-tetrahydro-pyran In 2-methyltetrahydrofuran at -20 - 20℃; for 3h; Inert atmosphere; Stage #3: With hydrogenchloride In 2-methyltetrahydrofuran; water at 0 - 20℃; | 86% |
biphenyl-4-ylmethyl (4R,5S)-2,2-di-tert-butyl-5-methyl-1,3,2-dioxasilolane-4-carboxylate
methylmagnesium chloride
A
biphenyl-4-yl methanol
B
(3R,4S)-4-((di-tert-butyl(methyl)silyl)oxy)-3-hydroxypentan-2-one
C
(3R,4S)-4-((di-tert-butyl(methyl)silyl)oxy)-2-methylpentane-2,3-diol
Conditions | Yield |
---|---|
Stage #1: biphenyl-4-ylmethyl (4R,5S)-2,2-di-tert-butyl-5-methyl-1,3,2-dioxasilolane-4-carboxylate; methylmagnesium chloride With N,O-dimethylhydroxylamine*hydrochloride In tetrahydrofuran at -10℃; for 0.166667h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water at -10℃; Inert atmosphere; regioselective reaction; | A 85% B 65% C 16% |
Conditions | Yield |
---|---|
Stage #1: 4'-biphenyl chloride With n-Butyl chloride; iodine; magnesium In 2-methyltetrahydrofuran at 60℃; for 2h; Inert atmosphere; Reflux; Stage #2: C4H11BrOSi In 2-methyltetrahydrofuran at -20 - 20℃; for 3h; Inert atmosphere; Stage #3: With hydrogenchloride In 2-methyltetrahydrofuran; water at 0 - 20℃; | 85% |
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; potassium acetate; palladium diacetate; tris-(o-tolyl)phosphine In 1-methyl-pyrrolidin-2-one at 110℃; for 4h; Schlenk technique; Inert atmosphere; | 85% |
4-methoxybenzenediazonium tetrafluoroborate
phenylboronic acid
biphenyl-4-yl methanol
Conditions | Yield |
---|---|
polystyrene-supported N-heterocyclic carbene-Pd complex In ethanol at 20℃; for 12h; Suzuki-Miyaura cross-coupling; | 84% |
Conditions | Yield |
---|---|
With sodium hydroxide In water at 20℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Green chemistry; | 84% |
With potassium carbonate In water at 70℃; for 12h; Catalytic behavior; Temperature; Reagent/catalyst; Suzuki Coupling; Green chemistry; | 100 %Chromat. |
Conditions | Yield |
---|---|
Stage #1: 4'-biphenyl chloride With n-Butyl chloride; iodine; magnesium In tetrahydrofuran at 60℃; for 2h; Inert atmosphere; Reflux; Stage #2: bromethyl methyl ether In tetrahydrofuran at -20 - 20℃; for 3h; Inert atmosphere; Stage #3: With hydrogen bromide In tetrahydrofuran at 0 - 10℃; | 84% |
4-bromo-1,1'-biphenyl
chloromethyl trimethylsilyl ether
biphenyl-4-yl methanol
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1,1'-biphenyl With n-Butyl chloride; iodine; magnesium In 2-methyltetrahydrofuran at 60℃; for 2h; Inert atmosphere; Reflux; Stage #2: trimethylsilyl chloromethyl ether In 2-methyltetrahydrofuran at -20 - 20℃; for 3h; Inert atmosphere; | 83% |
Conditions | Yield |
---|---|
Stage #1: 4'-biphenyl chloride With n-Butyl chloride; iodine; magnesium In tetrahydrofuran at 60℃; for 2h; Inert atmosphere; Reflux; Stage #2: C6H11ClO2 In tetrahydrofuran at -20 - 20℃; for 3h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0 - 20℃; | 83% |
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1,1'-biphenyl With n-Butyl chloride; iodine; magnesium In tetrahydrofuran at 60℃; for 2h; Inert atmosphere; Reflux; Stage #2: chloromethyl methyl ether In tetrahydrofuran at -20 - 20℃; for 3h; Inert atmosphere; Stage #3: With hydrogen bromide In tetrahydrofuran at 0 - 10℃; | 81% |
biphenyl-4-methylchloride
potassium carbonate
A
di(biphenyl-4-ylmethyl)carbonate
B
biphenyl-4-yl methanol
Conditions | Yield |
---|---|
With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 110℃; for 36h; | A 80% B 2% |
Conditions | Yield |
---|---|
With potassium phosphate; water; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In 1,4-dioxane at 20℃; Heating / reflux; | 80% |
Conditions | Yield |
---|---|
Stage #1: triallyl(phenyl)silane With tetrabutyl ammonium fluoride In water; dimethyl sulfoxide at 20℃; for 1h; Stage #2: 4-bromobenzenemethanol With tricyclohexylphosphine; palladium dichloride In water; dimethyl sulfoxide at 80℃; for 4h; | 79% |
Conditions | Yield |
---|---|
Stage #1: 4-iodo-benzyl alcohol With dilithium tetra(tert-butyl)zincate In tetrahydrofuran at 20℃; for 2h; Stage #2: iodobenzene With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 18h; | 73% |
Stage #1: 4-iodo-benzyl alcohol With dilithium tetra(tert-butyl)zincate In tetrahydrofuran at -78 - 20℃; Inert atmosphere; Stage #2: iodobenzene With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at -78 - 20℃; Inert atmosphere; chemoselective reaction; | 73% |
Conditions | Yield |
---|---|
With cesium fluoride In N,N-dimethyl-formamide at 70℃; | A 21% B 2% C 70% |
[1,1'-biphenyl]-4-ylmethyl methanesulfonate
biphenyl-4-yl methanol
Conditions | Yield |
---|---|
Multistep reaction; | 70% |
biphenyl-4-yl methanol
trichloroacetonitrile
4-phenylbenzyl trichloroacetimidate
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide In dichloromethane; water at 0 - 25℃; | 100% |
Stage #1: biphenyl-4-yl methanol With sodium hydride In diethyl ether; oil at 20℃; for 0.0833333h; Stage #2: trichloroacetonitrile In diethyl ether; oil at 20℃; for 2h; | 97% |
With sodium hydride In diethyl ether 1.) 20 min, 2.) r.t., 1 h; | 69% |
Conditions | Yield |
---|---|
With n-butyltriphenylphosphonium permanganate In acetonitrile at 20℃; for 0.25h; | 100% |
With silica-supported Jones reagent In dichloromethane for 0.00269444h; | 99.7% |
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N-methyl-N-[3-(4'-diacetoxyiodo)phenoxy-1-propyl]pyrrolidinium 4-methylbenzenesulfonate In dichloromethane at 20℃; for 6h; | 99% |
methyl 2-isocyanatobenzoate
biphenyl-4-yl methanol
methyl 2-({[(4-biphenylylmethyl)oxy]carbonyl}amino)benzoate
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; Heating / reflux; | 100% |
biphenyl-4-yl methanol
4-(azidomethyl)-1,1'-biphenyl
Conditions | Yield |
---|---|
Stage #1: biphenyl-4-yl methanol With 1,2-Diiodoethane; N,N-dimethyl-formamide; triphenylphosphine at 20℃; for 0.0166667h; Sealed tube; Inert atmosphere; Stage #2: With sodium azide at 20℃; Sealed tube; Inert atmosphere; | 100% |
With 2-azido-1,3-dimethyl-4,5-dihydro-1H-imidazol-3-ium hexafluorophosphate (V); 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 0.166667h; | 93% |
biphenyl-4-yl methanol
N-benzoyloxybenzotriazole
[1,1'-biphenyl]-4-ylmethyl benzoate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 100% |
Conditions | Yield |
---|---|
Stage #1: biphenyl-4-yl methanol With 1,2-Diiodoethane; N,N-dimethyl-formamide; triphenylphosphine at 50℃; for 0.0166667h; Sealed tube; Inert atmosphere; Stage #2: N-methylaniline at 50℃; Sealed tube; Inert atmosphere; | 100% |
sodium benzoate
biphenyl-4-yl methanol
[1,1'-biphenyl]-4-ylmethyl benzoate
Conditions | Yield |
---|---|
Stage #1: biphenyl-4-yl methanol With 1,2-Diiodoethane; N,N-dimethyl-formamide; triphenylphosphine at 20℃; for 0.0166667h; Sealed tube; Inert atmosphere; Stage #2: sodium benzoate at 20℃; Sealed tube; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With silica-supported Jones reagent In dichloromethane for 0.035h; | 99.5% |
With diethylene glycol dimethyl ether at 70℃; for 0.583333h; Sonication; | 96% |
With sodium tetrahydroborate; 1% Pd/C; water; potassium hydroxide In methanol at 20℃; for 6h; In air; | 89% |
Conditions | Yield |
---|---|
Stage #1: biphenyl-4-yl methanol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tert-butylhypochlorite In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #2: With ammonia; iodine In dichloromethane; water at 20℃; for 2h; Inert atmosphere; | 99% |
With ammonia; oxygen In tert-Amyl alcohol; water at 100℃; under 3750.38 Torr; for 6h; Autoclave; High pressure; | 99% |
With 1,4-diaza-bicyclo[2.2.2]octane; TEMPOL; ammonia; copper(l) chloride In water; acetonitrile at 20℃; for 24h; | 91% |
biphenyl-4-yl methanol
potassium acetate
[1,1’-biphenyl]-4-ylmethyl acetate
Conditions | Yield |
---|---|
Stage #1: biphenyl-4-yl methanol With 1,2-Diiodoethane; N,N-dimethyl-formamide; triphenylphosphine at 20℃; for 0.0166667h; Sealed tube; Inert atmosphere; Stage #2: potassium acetate at 20℃; Sealed tube; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With potassium hydroxide In diethyl ether at 20℃; for 12h; | 99% |
biphenyl-4-yl methanol
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
With fluorosulfonyl fluoride; caesium carbonate at 20℃; for 12h; Reagent/catalyst; Sealed tube; | 99% |
Conditions | Yield |
---|---|
With potassium tert-butylate In toluene at 120℃; for 3h; Inert atmosphere; | 99% |
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium tert-butylate In toluene at 120℃; for 18h; Inert atmosphere; Sealed tube; | 73% |
Conditions | Yield |
---|---|
With bromine; triphenylphosphine In dichloromethane at -78 - 20℃; for 18h; Inert atmosphere; | 98% |
With bromine; triphenylphosphine In dichloromethane at -78 - 25℃; for 18h; | 97% |
With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 1.5h; | 95% |
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; potassium tert-butylate; nickel diacetate In 1,4-dioxane; toluene at 80℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; | 98% |
With [2,2]bipyridinyl; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); potassium tert-butylate at 140℃; for 18h; | 89% |
With potassium tert-butylate In 1,3,5-trimethyl-benzene at 164℃; for 6h; | 75% |
biphenyl-4-yl methanol
[1,1'-biphenyl]-4-ylmethyl benzoate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 98% |
biphenyl-4-yl methanol
sodium phenoxide
1-phenyl-4-phenoxymethylbenzene
Conditions | Yield |
---|---|
Stage #1: biphenyl-4-yl methanol With 1,2-Diiodoethane; N,N-dimethyl-formamide; triphenylphosphine at 20℃; for 0.0166667h; Sealed tube; Inert atmosphere; Stage #2: sodium phenoxide at 20℃; Sealed tube; Inert atmosphere; | 98% |
biphenyl-4-yl methanol
Conditions | Yield |
---|---|
With 3,3-dimethyl-2-nitroso-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide; trifluoroacetic acid In acetonitrile at 20℃; for 0.5h; Temperature; Solvent; Sealed tube; | 98% |
5-Fluoro-4-trifluoromethyl-2-phenyloxazole
biphenyl-4-yl methanol
5-(Biphenyl-4-ylmethoxy)-2-phenyl-4-trifluoromethyl-oxazole
Conditions | Yield |
---|---|
With potassium hydroxide In 1,4-dioxane | 97% |
Conditions | Yield |
---|---|
With magnesium hydrogen sulfate at 20℃; for 4h; | 97% |
biphenyl-4-yl methanol
phenyl 2,3,4-tri-O-benzyl-6-O-[2-[(4-phenylbenzyl)oxycarbonyl]benzoyl]-1-thio-α-D-glucopyranoside
Conditions | Yield |
---|---|
With dacarbazine; dmap In dichloromethane | 97% |
biphenyl-4-yl methanol
acetic anhydride
[1,1’-biphenyl]-4-ylmethyl acetate
Conditions | Yield |
---|---|
With colloidal gold nanoparticle-supported gadolinium complex In N,N-dimethyl-formamide for 0.0166667h; Reagent/catalyst; Microwave irradiation; | 97% |
Conditions | Yield |
---|---|
With oxygen In toluene at 90℃; Sealed tube; | 97% |
IUPAC Name: 4-Biphenylmethanol
The MF of 4-Biphenylmethanol (3597-91-9) is C13H12O.
The MW of 4-Biphenylmethanol (3597-91-9) is 184.23.
Synonyms of 4-Biphenylmethanol (3597-91-9): [1,1'-Biphenyl]-4-methanol ; 4-Biphenylylmethanol ; Biphenyl-4-ylmethanol ; 4-(Hydroxymethyl)biphenyl
Product Categories: Biphenyl derivatives
Form: white to beige powder
Index of Refraction: 1.595
EINECS: 222-745-2
Density: 1.093 g/ml
Flash Point: 154.9 °C
Boiling Point: 340 °C
Melting Point: 99-101 °C
BRN: 1937761
Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes.
Safety information of 4-Biphenylmethanol (3597-91-9):
Hazard Codes Xn
Risk Statements
20/21/22 Harmful by inhalation, in contact with skin and if swallowed
36/37/38 Irritating to eyes, respiratory system and skin
Safety Statements
22 Do not breathe dust
24/25 Avoid contact with skin and eyes
36 Wear suitable protective clothing
26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany 3
RTECS DV5425000
HS Code 29062900
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