6,6-diisopropyldibenzo[d,f][1,3,2]dioxasilepine
2,2'-dihydroxybiphenyl
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; | 100% |
3,3',5,5'-tetra(tert-butyl)biphenyl-2,2'-diol
A
2,2'-dihydroxybiphenyl
B
4-tert-butyltoluene
Conditions | Yield |
---|---|
With Nafion-H; toluene for 2h; Heating; | A 98% B 98 % Chromat. |
3,3',5,5'-tetra(tert-butyl)biphenyl-2,2'-diol
toluene
A
2,2'-dihydroxybiphenyl
B
4-tert-butyltoluene
Conditions | Yield |
---|---|
With Nafion-H for 2h; Heating; | A 98% B 98 % Chromat. |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; potassium carbonate In water at 80℃; for 2.5h; Suzuki-Miyaura Coupling; Inert atmosphere; | 98% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In N,N-dimethyl-formamide at 160℃; for 0.5h; Suzuki Coupling; Microwave irradiation; | |
With palladium on activated charcoal; potassium carbonate In water at 80℃; Suzuki Coupling; |
2,2'-dihydroxybiphenyl
Conditions | Yield |
---|---|
With sulfuric acid at 100℃; for 2h; | 98% |
Conditions | Yield |
---|---|
With aluminium trichloride In ethanethiol for 0.5h; Ambient temperature; | 97.5% |
With aluminium trichloride In ethanethiol for 0.5h; Ambient temperature; | 97.5% |
C30H50O2Si2
2,2'-dihydroxybiphenyl
Conditions | Yield |
---|---|
With potassium fluoride In Tetraethylene glycol at 20℃; for 0.5h; Inert atmosphere; | 96% |
With potassium fluoride; Tetraethylene glycol at 20℃; for 0.5h; | 96% |
2,2'-biphenol bis(tert-butyldimethylsilyl) ether
2,2'-dihydroxybiphenyl
Conditions | Yield |
---|---|
With lithium acetate In water; N,N-dimethyl-formamide at 70℃; for 6h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water at 50℃; | 92% |
With hydrogenchloride; water In ethanol at 50℃; | 92% |
Conditions | Yield |
---|---|
With potassium carbonate In ethanol; water at 20℃; for 12h; Ullmann Condensation; | 92% |
2-hydroxybromobenzene
2-hydroxyphenyl boronic acid
2,2'-dihydroxybiphenyl
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; potassium hydroxide at 150℃; for 0.5h; Suzuki-Miyaura Coupling; Microwave irradiation; Inert atmosphere; | 83% |
With palladium 10% on activated carbon; potassium hydroxide In water at 150℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere; Microwave irradiation; | 83% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; palladium diacetate; caesium carbonate; Trimethylacetic acid In water; acetonitrile at 80℃; for 18h; Reagent/catalyst; Time; Sealed tube; regioselective reaction; | 76% |
With palladium diacetate; caesium carbonate; Trimethylacetic acid In acetonitrile at 80℃; for 24h; | 74% |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; potassium acetate; bis(pinacol)diborane In ethanol at 60℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; | 75.5% |
With NaH-t-AmONa-Ni(OAc)2-bpy-KI In tetrahydrofuran; benzene at 63℃; for 0.5h; | 63% |
Multi-step reaction with 5 steps 1: sodium hydride / N,N-dimethyl-formamide 2: sulfuryl dichloride / dichloromethane 3: potassium carbonate / N,N-dimethyl-formamide 4: 1,10-Phenanthroline; potassium tert-butylate / pyridine / 2 h / 120 °C / Microwave irradiation; Inert atmosphere 5: hydrogenchloride / ethanol; water / 50 °C View Scheme |
2,2'-dihydroxybiphenyl
Conditions | Yield |
---|---|
With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran at 0℃; for 4h; | 70% |
2-hydroxyphenyl boronic acid
2,2'-dihydroxybiphenyl
Conditions | Yield |
---|---|
With nano-CuO-grafted triazine-functionalized covalent organic framework In methanol at 60℃; Catalytic behavior; | 68% |
6-diazo-2-cyclohexen-1-one
1-iodo-2-(tert-butyldimethylsilyloxy)benzene
2,2'-dihydroxybiphenyl
Conditions | Yield |
---|---|
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 50℃; for 36h; Inert atmosphere; | 64% |
1-Chloro-4-fluorobenzene
2-hydroxybromobenzene
A
2,2'-dihydroxybiphenyl
B
4,4'-difluorobiphenyl
C
4'-fluoro-[1,1'-biphenyl]-2-ol
Conditions | Yield |
---|---|
With NaH-t-AmONa-Ni(OAc)2-bpy-KI In tetrahydrofuran; benzene at 63℃; for 3h; Yields of byproduct given; | A n/a B n/a C 43% |
2-hydroxybromobenzene
4-chlorobenzotrifluoride
A
2,2'-dihydroxybiphenyl
B
4,4'-bis(trifluoromethyl)biphenyl
C
4′-(trifluoromethyl)[1,1′-biphenyl]-2-ol
Conditions | Yield |
---|---|
With NaH-t-AmONa-Ni(OAc)2-bpy-KI In tetrahydrofuran; benzene at 63℃; for 2h; Yields of byproduct given; | A n/a B n/a C 40% |
2-hydroxybromobenzene
1-chloro-2-(trifluoromethyl)benzene
A
2,2'-dihydroxybiphenyl
B
2,2’-bis(trifluoromethyl)-1,1’-biphenyl
C
2-(trifluoromethyl)-2'-hydroxybiphenyl
Conditions | Yield |
---|---|
With NaH-t-AmONa-Ni(OAc)2-bpy-KI In tetrahydrofuran; benzene at 63℃; for 3.5h; Yields of byproduct given; | A n/a B n/a C 35% |
1-chloro-2-fluorobenzene
2-hydroxybromobenzene
A
2,2'-dihydroxybiphenyl
B
2,2'-difluorobiphenyl
C
2'-fluoro-[1,1'-biphenyl]-2-ol
Conditions | Yield |
---|---|
With NaH-t-AmONa-Ni(OAc)2-bpy-KI In tetrahydrofuran; benzene at 63℃; for 3h; Yields of byproduct given; | A n/a B n/a C 34% |
N-(phenoxy)-4-methylbenzenesulfonamide
phenol
A
2,2'-dihydroxybiphenyl
B
4,4'-Dihydroxybiphenyl
C
2,4'-dihydroxybiphenyl
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; trifluoroacetic acid at 0℃; for 1h; | A 9.2% B 27.6 % Chromat. C 32.7% |
With trifluorormethanesulfonic acid; trifluoroacetic acid at 0℃; for 1h; | A 9.2 % Chromat. B 27.6 % Chromat. C 32.7 % Chromat. |
1-chlorodibenzo-p-dioxin
B
2,2'-dihydroxybiphenyl
Conditions | Yield |
---|---|
In methanol at 20℃; for 3h; Irradiation; | A 11.7% B 18.8% |
1,2-dichlorodibenzo-p-dioxin
2,2'-dihydroxybiphenyl
Conditions | Yield |
---|---|
In methanol at 20℃; for 1h; Irradiation; | 13% |
Multi-step reaction with 2 steps 1: 58.5 percent / acetophenone / methanol / 1 h / 20 °C / Irradiation 2: 18.8 percent / methanol / 3 h / 20 °C / Irradiation View Scheme |
phenol
A
2,2'-dihydroxybiphenyl
B
benzene-1,2-diol
C
hydroquinone
Conditions | Yield |
---|---|
With 3,10-di-n-butylisoalloxazine N-oxide In acetonitrile for 6h; Irradiation; Yields of byproduct given; | A 2% B n/a C n/a |
Conditions | Yield |
---|---|
With potassium hydroxide; sodium hydroxide at 400 - 410℃; im Eisenrohr; | |
With potassium hydroxide; 9H-carbazole at 250 - 275℃; | |
With potassium hydroxide; 9H-fluorene at 250 - 275℃; | |
With indole; potassium hydroxide at 250 - 275℃; | |
With potassium hydroxide; phenanthrene at 200 - 230℃; |
6,6'-dihydroxy-1,1'-biphenyl-3,3'-dicarboxylic acid
A
dibenzofuran
B
2,2'-dihydroxybiphenyl
Conditions | Yield |
---|---|
With hydrogenchloride at 270℃; |
Conditions | Yield |
---|---|
With potassium permanganate; sulfuric acid | |
coupling; |
dioxin
A
1-hydroxydibenzofuran
B
2-Phenoxyphenol
C
2,2'-dihydroxybiphenyl
Conditions | Yield |
---|---|
In acetonitrile at 12℃; Mechanism; Irradiation; also 2,3,7,8-tetrachlorodibenzo-1,4-dioxin (TCDD), also with NaBH4 in aq. MeCN; |
phenoxy radical
A
2-Phenoxyphenol
B
2,2'-dihydroxybiphenyl
C
4,4'-Dihydroxybiphenyl
D
2,4'-dihydroxybiphenyl
E
4-Phenoxyphenol
Conditions | Yield |
---|---|
Product distribution; Irradiation; effect of abs. dose of irrad.; |
phenol
dibenzoyl peroxide
A
6H-benzo[c]chromen-6-one
B
benzoic acid phenyl ester
C
2,2'-dihydroxybiphenyl
D
2-hydroxyphenyl benzoate
Conditions | Yield |
---|---|
at 60℃; for 3h; Product distribution; | A 0.1 % Chromat. B 8 % Chromat. C 6 % Chromat. D 82 % Chromat. |
at 60℃; for 3h; | A 0.1 % Chromat. B 8 % Chromat. C 6 % Chromat. D 82 % Chromat. |
2,2'-dihydroxybiphenyl
6-chloro-dibenzo[d,f][1,3,2]-dioxaphosphepin
Conditions | Yield |
---|---|
With phosphorus trichloride for 2h; Inert atmosphere; Reflux; | 100% |
With trichlorophosphate at 20 - 50℃; under 150.015 - 675.068 Torr; Inert atmosphere; | 99% |
With phosphorus trichloride In toluene at 20℃; under 525.053 - 675.068 Torr; for 0.25h; Inert atmosphere; | 99% |
2,2'-dihydroxybiphenyl
3,3′,5,5′-tetrabromo-[1,1′-biphenyl]-2,2′-diol
Conditions | Yield |
---|---|
With bromine; acetic acid | 100% |
With bromine In methanol at 0 - 20℃; for 8h; | 90% |
With bromine In methanol for 1h; | 76% |
2,2'-dihydroxybiphenyl
trifluoromethylsulfonic anhydride
2,2'-bis-<<(trifluoromethyl)sulfonyl>oxy>biphenyl
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0℃; Inert atmosphere; | 100% |
With triethylamine In dichloromethane at 0 - 23℃; for 14h; | 99% |
With pyridine | 97% |
2,2'-dihydroxybiphenyl
(S)-1-phenyl-ethylamine
((S)-1-Phenyl-ethyl)-(6-thioxo-5,7-dioxa-6λ5-phospha-dibenzo[a,c]cyclohepten-6-yl)-amine
Conditions | Yield |
---|---|
With pyridine; trichlorothiophosphine | 100% |
2,2'-dihydroxybiphenyl
chloromethyl methyl ether
2,2'-bis(methoxymethoxy)-1,1'-biphenyl
Conditions | Yield |
---|---|
With sodium hydride | 100% |
Stage #1: 2,2'-dihydroxybiphenyl With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.5h; Cooling with ice; Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; | 100% |
Stage #1: 2,2'-dihydroxybiphenyl With sodium hydride In tetrahydrofuran; DMF (N,N-dimethyl-formamide); water at 0℃; for 0.166667h; Stage #2: chloromethyl methyl ether In tetrahydrofuran; DMF (N,N-dimethyl-formamide) at 20℃; for 8h; | 97% |
2,2'-dihydroxybiphenyl
5,5'-dibromo-2,2'-dihydroxybiphenyl
Conditions | Yield |
---|---|
With bromine In dichloromethane at -78℃; | 99% |
With bromine In chloroform Bromination; | 97% |
With bromine In dichloromethane | 95% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 63℃; for 24h; | 99% |
With potassium carbonate In toluene at 60 - 70℃; | 99% |
With potassium carbonate In acetone for 8h; Heating; | 98% |
2,2'-dihydroxybiphenyl
4,6-(bis[bis-diethylamido]phosphonito)-2,8-dimethyl-phenoxathiine
4,6-bis(dibenzo[d,f][1,3,2]dioxaphosphino-1-yl)-2,8-dimethylphenoxathiine
Conditions | Yield |
---|---|
In toluene at 109.9℃; for 15h; | 99% |
2,2'-dihydroxybiphenyl
allyl methyl carbonate
2,2′-di(allyloxy)-biphenyl
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran at 25℃; for 24h; Condensation; | 99% |
2,2'-dihydroxybiphenyl
5-bromo-2,2'-dihydroxybiphenyl
Conditions | Yield |
---|---|
With Diethyl 2-bromomalonate at 100℃; for 48h; Product distribution; Further Variations:; Reagents; | 99% |
With bromine In dichloromethane at 20℃; for 24h; | 40% |
2,2'-dihydroxybiphenyl
i-pentyl bromide
2'-(isopentyloxy)-[1,1'-biphenyl]-2-ol
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 19.5h; Heating / reflux; | 99% |
With potassium carbonate In acetone Reflux; | 99% |
With potassium carbonate In acetone at 56℃; for 24h; | 89% |
2,2'-dihydroxybiphenyl
Isopropyl isocyanate
2,2'-bis(isopropylcarbamoyloxy)biphenyl
Conditions | Yield |
---|---|
With dmap In tetrahydrofuran at 60℃; for 24h; | 99% |
2,2'-dihydroxybiphenyl
C24H18O2P2Se4
Conditions | Yield |
---|---|
In toluene for 7h; Reflux; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
Stage #1: 2,2'-dihydroxybiphenyl With pyridine; 1-methyl-1H-imidazole; phosphorus trichloride In tetrahydrofuran at 90℃; for 5h; Stage #2: 3,3',5,5'-tetra(tert-butyl)biphenyl-2,2'-diol In tetrahydrofuran at 100℃; for 11h; Reagent/catalyst; Time; | 99% |
Stage #1: 2,2'-dihydroxybiphenyl With 1-methyl-1H-imidazole; phosphorus trichloride In toluene at 90℃; for 3h; Stage #2: 3,3',5,5'-tetra(tert-butyl)biphenyl-2,2'-diol With pyridine In toluene at 100℃; for 11h; Reagent/catalyst; Solvent; Temperature; | 99% |
Stage #1: 2,2'-dihydroxybiphenyl With pyridine; phosphorus trichloride In toluene at 0 - 35℃; for 18h; Stage #2: 3,3',5,5'-tetra(tert-butyl)biphenyl-2,2'-diol In toluene at 5 - 35℃; |
2,2'-dihydroxybiphenyl
2-(2-Chloroethoxy)ethanol
2,2'-bis(5-hydroxy-3-oxa-1-pentyloxy)-1,1'-biphenyl
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 24h; | 98% |
2,2'-dihydroxybiphenyl
2,2'-dihydroxy-3,3'-di-tert-butyl-5,5'-dimethoxy-1,1'-biphenyl
6,6′-[(3,3′-di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy)]bis(di-benzo[d,f][1,3,2]dioxaphosphepin)
Conditions | Yield |
---|---|
Stage #1: 2,2'-dihydroxybiphenyl With pyridine; phosphorus trichloride In tetrahydrofuran for 6h; Stage #2: 2,2'-dihydroxy-3,3'-di-tert-butyl-5,5'-dimethoxy-1,1'-biphenyl In tetrahydrofuran at 100℃; for 11h; Concentration; | 98% |
Conditions | Yield |
---|---|
With tris(2,2'-bipyridyl)ruthenium dichloride In acetonitrile at 20℃; for 16h; Irradiation; | 98% |
2,2'-dihydroxybiphenyl
ortho-nitrofluorobenzene
2,2'-bis-(2-nitrophenoxy)-biphenyl
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran for 72h; Heating; | 97.2% |
Conditions | Yield |
---|---|
Stage #1: 2,2'-dihydroxybiphenyl With potassium carbonate In acetone at 20℃; for 0.166667h; Inert atmosphere; Stage #2: dimethyl sulfate In acetone at 20℃; for 12h; Inert atmosphere; | 97% |
With potassium carbonate at 60℃; for 1.5h; Williamson synthesis; | 95% |
With sodium hydroxide | 95% |
2,2'-dihydroxybiphenyl
Conditions | Yield |
---|---|
With dimethylsulfide borane complex In dichloromethane at 20℃; | 97% |
2,2'-dihydroxybiphenyl
chlorodicyclohexylphosphane
(C6H4OP(cyclohexyl)2)2
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 60℃; | 97% |
Conditions | Yield |
---|---|
With NH3 In ethanol; water bubbling NH3 through soln. of Tl-salt (in aq. EtOH), addn. of ligand (in EtOH); crystn. (24 h), filtration, washing (EtOH), drying (vac.); may be recrystallized from hot water; | 97% |
2,2'-dihydroxybiphenyl
dimethylsulfide borane complex
Conditions | Yield |
---|---|
In dichloromethane under N2 atm. BH3*SMe2 was added dropwise at 0°C soln. 2,2'-dihydroxybiphenyl in CH2Cl2, soln. was allowed to warm to room temp. and stirred for 14 h; volatiles were evapd., residue was washed with Et2O, dried in vacuo, andcrystd. from CH2Cl2-hexane (1:1); elem. anal.; | 97% |
Conditions | Yield |
---|---|
In toluene Heating; | 97% |
Molecular Structure of 2,2'-Biphenyldiol (CAS NO.1806-29-7):
IUPAC Name: 2-(2-Hydroxyphenyl)phenol
Canonical SMILES: C1=CC=C(C(=C1)C2=CC=CC=C2O)O
InChI: InChI=1S/C12H10O2/c13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)14/h1-8,13-14H
InChIKey: IMHDGJOMLMDPJN-UHFFFAOYSA-N
Molecular Weight: 186.2066 [g/mol]
Molecular Formula: C12H10O2
XLogP3: 3
H-Bond Donor: 2
H-Bond Acceptor: 2
EINECS: 217-303-0
Water Solubility: insoluble
Appearance: Beige to greyish-beige powder
Melting Point: 108-110 °C
Index of Refraction: 1.639
Molar Refractivity: 54.6 cm3
Molar Volume: 151.5 cm3
Surface Tension: 53.8 dyne/cm
Density: 1.228 g/cm3
Flash Point: 160.8 °C
Enthalpy of Vaporization: 57.84 kJ/mol
Boiling Point: 315 °C at 760 mmHg
Vapour Pressure: 0.000243 mmHg at 25 °C
Classification Code: Mutation data
Product Categories: Aromatic Phenols; Biphenyls (for High-Performance Polymer Research); Color Former & Related Compounds; Developer; Functional Materials; Reagent for High-Performance Polymer Research
2,2'-Biphenyldiol (CAS NO.1806-29-7) is used as pharmaceutical intermediates.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 150mg/kg (150mg/kg) | National Technical Information Service. Vol. AD691-490, | |
mouse | LD50 | intravenous | 56mg/kg (56mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#07870, |
Reported in EPA TSCA Inventory.
Poison by intraperitoneal and intravenous routes. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes :Xi,Xn
Risk Statements: 36/37/38-41-22
R22: 2,2'-Biphenyldiol (CAS NO.1806-29-7) is harmful if swallowed.
R41:Risk of serious damage to the eyes.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 2
RTECS: DV4200000
F: 8-9-23
2,2'-Biphenyldiol (CAS NO.1806-29-7), its Synonyms are 2,2'-Biphenol ; 2,2'-Dihydroxybiphenyl ; 2,2'-Dihydroxydiphenyl ; O,O'-Biphenol ; o,o'-Biphenol ; o,o'-Dihydroxybiphenyl ; o,o'-Diphenol ; o-Dihydroxydiphenyl ; (1,1'-Biphenyl)-2,2'-diol ; Biphenyl-2,2'-diol .
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