1-bromo-4-tert-butylbenzene
4-tert-butylphenylboronic acid
Conditions | Yield |
---|---|
Stage #1: 1-bromo-4-tert-butylbenzene With n-butyllithium In tetrahydrofuran at -78 - -45℃; for 3h; Stage #2: With boric acid tributyl ester In tetrahydrofuran at -78 - 20℃; Stage #3: Acid hydrolysis; | 90% |
Stage #1: 1-bromo-4-tert-butylbenzene With magnesium In tetrahydrofuran Heating; Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃; Stage #3: With hydrogenchloride | 80% |
Stage #1: 1-bromo-4-tert-butylbenzene With Trimethyl borate In tetrahydrofuran at -20 - 0℃; Inert atmosphere; Stage #2: With sulfuric acid In tetrahydrofuran at 0 - 10℃; for 10h; Inert atmosphere; | 72.8% |
water
4-tert-butylphenylboronic acid
Conditions | Yield |
---|---|
With 1H-imidazole; iron(III) chloride at 20℃; for 0.25h; Inert atmosphere; | 85% |
Trimethyl borate
1-bromo-4-tert-butylbenzene
4-tert-butylphenylboronic acid
Conditions | Yield |
---|---|
Stage #1: 1-bromo-4-tert-butylbenzene With magnesium In tetrahydrofuran Stage #2: Trimethyl borate In tetrahydrofuran; diethyl ether at -70 - 20℃; | 83.4% |
With magnesium In tetrahydrofuran; diethyl ether aryl bromide soln. dropped to Mg in THF, filtered, Grignard soln. added dropwise to soln. of calcd. amt. of B compd. in Et2O at -70°C, warming to room temp. overnight; mixt. added to ice cold and concd. aq. H2SO4, stirred for 30 min, extd. with ether (repeatedly), dried with Na2SO4, evapn., dried in vac., elem.anal.; | 83.4% |
With Mg; H2SO4 In tetrahydrofuran; diethyl ether aryl bromide in THF was added to Mg turnings, filtered, added dropwise with stirring to trimethyl borate in ether at -70°C, the suspn. was allowed to warm to room temp. overnight, added with stirring to ice, concd. H2SO4, stirred for 30 min (Ar); shaken with ether, dried over Na2SO4, evapd., filtered, dried in vac.; elem. anal.; | 83.4% |
boric acid tributyl ester
1-bromo-4-tert-butylbenzene
4-tert-butylphenylboronic acid
Conditions | Yield |
---|---|
With sulfuric acid; magnesium In diethyl ether; water | 10% |
tert-butylbenzene
4-tert-butylphenylboronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 100 percent / Br2; I2 / 0 °C 2.1: n-BuLi / tetrahydrofuran / 3 h / -78 - -45 °C 2.2: tributyl borate / tetrahydrofuran / -78 - 20 °C 2.3: 90 percent / Acid hydrolysis View Scheme |
4-tert-butylphenylboronic dimethyl ester
4-tert-butylphenylboronic acid
Conditions | Yield |
---|---|
With hydrogenchloride; water In tetrahydrofuran; hexane at 20℃; pH=3 - 5; |
Conditions | Yield |
---|---|
In chloroform-d1 at 25℃; Equilibrium constant; Sealed tube; |
A
4-(tert-butyl)-1,2-diaminobenzene
B
4-tert-butylphenylboronic acid
Conditions | Yield |
---|---|
In chloroform-d1 at 25℃; Equilibrium constant; Sealed tube; |
tetrahydroxydiboron
1-bromo-4-tert-butylbenzene
4-tert-butylphenylboronic acid
Conditions | Yield |
---|---|
With potassium tert-butylate In methanol at 0 - 20℃; |
4-tert-butylphenylboronic acid
Conditions | Yield |
---|---|
With sodium hydroxide In toluene | 100% |
ethyl 2-iodobenzoate
4-tert-butylphenylboronic acid
4'-tert-butylbiphenyl-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide for 18h; Heating / reflux; | 100% |
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane for 90h; Heating / reflux; |
3-(nitromethylene)oxetane
4-tert-butylphenylboronic acid
3-(4-tert-butylphenyl)-3-(nitromethyl)oxetane
Conditions | Yield |
---|---|
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; water; potassium hydroxide In 1,4-dioxane at 20℃; for 2h; | 100% |
para-bromotoluene
4-tert-butylphenylboronic acid
Conditions | Yield |
---|---|
With C21H26Cl2N2Pd; potassium carbonate In toluene at 110℃; for 18h; Suzuki Coupling; Inert atmosphere; Sealed tube; | 100% |
With C21H15ClN2O2Pd; potassium carbonate In water at 50℃; for 0.0833333h; Suzuki-Miyaura Coupling; | 98% |
With C22H26N2O6Pd2; potassium carbonate In isopropyl alcohol at 20℃; for 17h; Suzuki-Miyaura Coupling; | 98% |
4-tert-butylphenylboronic acid
para-tert-butylphenol
Conditions | Yield |
---|---|
With water; 3-chloro-benzenecarboperoxoic acid In ethanol at 20℃; for 6h; | 100% |
With dihydrogen peroxide In water at 20℃; for 0.166667h; | 98% |
With 3,4,5-trihydroxybenzoic acid; sodium hydrogencarbonate In ethanol; water at 20℃; for 24h; Reagent/catalyst; Solvent; Green chemistry; | 98% |
7-chloro-2-cyclohexylmethylindan-1-one
4-tert-butylphenylboronic acid
7-(4'-tert-butylphenyl)-2-cyclohexylmethylindan-1-one
Conditions | Yield |
---|---|
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; palladium diacetate In water; ethylene glycol at 125℃; Inert atmosphere; | 100% |
With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate In water; ethylene glycol at 125℃; for 4h; Inert atmosphere; | 100% |
7-chloro-2-(2,2-dimethylpropyl)indan-1-one
4-tert-butylphenylboronic acid
7-(4'-tert-butylphenyl)-2-(2,2-dimethylpropyl)indan-1-one
Conditions | Yield |
---|---|
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; palladium diacetate In water; ethylene glycol at 125℃; Inert atmosphere; | 100% |
With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate In water; ethylene glycol at 125℃; for 4h; Inert atmosphere; | 100% |
4-tert-butylphenylboronic acid
Conditions | Yield |
---|---|
With trisodium tris(3-sulfophenyl)phosphine; sodium carbonate; palladium diacetate In water; ethylene glycol at 125℃; Inert atmosphere; | 100% |
8-methyl-1,5-naphthyridin-4-yl trifluoromethanesulfonate
4-tert-butylphenylboronic acid
4-(4-(tert-butyl)phenyl)-8-methyl-1,5-naphthyridine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane at 80℃; for 1h; Suzuki Coupling; | 100% |
Stage #1: 8-methyl-1,5-naphthyridin-4-yl trifluoromethanesulfonate; p-tert-butylphenylboronic acid With sodium carbonate In 1,2-dimethoxyethane for 0.25h; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane at 80℃; for 1h; | 100% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane at 80℃; for 1h; Inert atmosphere; | 100% |
o-iodo-methyl-benzoic acid
4-tert-butylphenylboronic acid
methyl 4′-(tert butyl)-[1,1′-biphenyl]-2-carboxylate
Conditions | Yield |
---|---|
With bis(triphenylphosphine)palladium(II) dichloride; sodium carbonate In tetrahydrofuran; water at 80℃; for 14h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; Sealed tube; | 100% |
With palladium diacetate; sodium carbonate In water; acetonitrile at 60℃; Suzuki-Miyaura Coupling; Inert atmosphere; | 90% |
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water at 20 - 80℃; Suzuki Coupling; Schlenk technique; Inert atmosphere; | |
With potassium phosphate; palladium diacetate; triphenylphosphine In toluene at 80℃; Inert atmosphere; Schlenk technique; |
Conditions | Yield |
---|---|
Stage #1: 3-methoxy-thiophene With N-Bromosuccinimide In tetrahydrofuran Stage #2: p-tert-butylphenylboronic acid With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium hydroxide; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran at 60℃; | 100% |
Stage #1: 3-methoxy-thiophene With N-Bromosuccinimide Inert atmosphere; Stage #2: p-tert-butylphenylboronic acid With bis(tri-t-butylphosphine)palladium(0) Inert atmosphere; |
4-tert-butylphenylboronic acid
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 0.166667h; | 100% |
7-chloro-2-(1-adamantylmethyl)indan-1-one
4-tert-butylphenylboronic acid
7-(4'-tert-butylphenyl)-2-(1-adamantylmethyl)indan-1-one
Conditions | Yield |
---|---|
With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate In water at 125℃; for 6h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 80℃; for 24h; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate; palladium dichloride In ethanol; water at 20℃; for 0.0833333h; Suzuki cross-coupling; | 99% |
With potassium carbonate In ethanol; water at 50℃; for 0.75h; Catalytic behavior; Suzuki Coupling; Microwave irradiation; | 99.5% |
With potassium carbonate In ethanol; water at 80℃; for 10h; Catalytic behavior; Suzuki Coupling; | 99.5% |
cyclohexenone
4-tert-butylphenylboronic acid
(R)-3-(4-(tert-butyl)phenyl)cyclohexan-1-one
Conditions | Yield |
---|---|
With chlorobis(ethylene)rhodium(I) dimer; (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphine; potassium hydroxide In water; toluene at 20 - 40℃; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
Stage #1: p-tert-butylphenylboronic acid With chlorobis(ethylene)rhodium(I) dimer; (S)-cinnamyl-2,3-dihydro-1,2-benzoisothiazole 1-oxide In 1,4-dioxane at 40℃; for 0.5h; Inert atmosphere; Sealed tube; Stage #2: cyclohexenone With potassium phosphate In 1,4-dioxane; water at 40℃; for 3h; Inert atmosphere; Sealed tube; enantioselective reaction; | 98% |
With potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; (R)-1-(tert-butylsulfinyl)-2-(prop-1-en-2-yl)benzene In methanol; dichloromethane; water at 40℃; for 3h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 97% |
4-tert-butylphenylboronic acid
4,4'-di-tert-butylbiphenyl
Conditions | Yield |
---|---|
With iodine; oxygen; potassium carbonate In PEG-400 at 140℃; for 48h; | 99% |
With copper fluorapatite In methanol at 20℃; for 2h; Green chemistry; | 96% |
With copper(II) choride dihydrate; sodium carbonate In methanol at 25℃; for 0.25h; Catalytic behavior; Reagent/catalyst; Solvent; Green chemistry; | 95% |
1-bromo-4-methoxy-benzene
4-tert-butylphenylboronic acid
Conditions | Yield |
---|---|
With potassium carbonate; palladium dichloride In ethanol; water at 20℃; for 0.0833333h; Suzuki cross-coupling; | 99% |
With 4Pd(2+)*8NO3(1-)*4C12H10*4C24H18N6O4; potassium carbonate In ethanol; water at 55℃; for 10h; Reagent/catalyst; Suzuki-Miyaura Coupling; | 99% |
With C21H20N2O2Pd; potassium carbonate In water; isopropyl alcohol at 25℃; for 0.5h; Suzuki-Miyaura Coupling; | 98% |
N-acetyl-2-bromoaniline
4-tert-butylphenylboronic acid
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium phosphate In toluene at 90℃; for 4h; Suzuki-Miyaura coupling; | 99% |
(4-bromophenyl)-(9H-β-carbolin-1-yl)-methanone
4-tert-butylphenylboronic acid
C28H24N2O
Conditions | Yield |
---|---|
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene at 90℃; for 24h; Suzuki-Miyaura coupling; | 99% |
(3-bromophenyl)-(9H-β-carbolin-1-yl)-methanone
4-tert-butylphenylboronic acid
C28H24N2O
Conditions | Yield |
---|---|
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene at 90℃; for 24h; Suzuki-Miyaura coupling; | 99% |
4-tert-butylphenylboronic acid
phenylacetylene
[(4-tert-butylphenyl)ethynyl]benzene
Conditions | Yield |
---|---|
With sodium perchlorate; palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,2,6,6-tetramethyl-4-benzoyloxypiperidine-1-oxide In water; acetonitrile at 20℃; Inert atmosphere; Electrochemical reaction; | 99% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 70℃; for 15h; Inert atmosphere; | 99% |
With di-μ-bromobis(tri-tert-butylphosphino)dipalladium(I); potassium hydroxide In tetrahydrofuran for 0.666667h; Reflux; | 97% |
With potassium phosphate tribasic heptahydrate; oxygen; palladium diacetate In isopropyl alcohol at 80℃; Suzuki Coupling; | 80% |
1-methoxy-4-(2-nitro-vinyl)-benzene
4-tert-butylphenylboronic acid
Conditions | Yield |
---|---|
With chlorobis(ethylene)rhodium(I) dimer; tert-butanesulfinylphosphine; triethylamine In ethanol at 40℃; for 10h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
cyclohexenone
4-tert-butylphenylboronic acid
(S)-3-(4-(tert-butyl)phenyl)cyclohexanone
Conditions | Yield |
---|---|
With chlorobis(ethylene)rhodium(I) dimer; C16H23NO3S; potassium hydroxide In 1,4-dioxane; water at 70℃; for 10h; Inert atmosphere; enantioselective reaction; | 99% |
With potassium fluoride; chlorobis(ethylene)rhodium(I) dimer; (R,E)-1-(tert-butylsulfinyl)-2-(prop-1-enyl)benzene In methanol; dichloromethane; water at 40℃; for 3h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 98% |
Stage #1: cyclohexenone; p-tert-butylphenylboronic acid With C50H48Cl2O2Rh2S2 In 1,4-dioxane at 40℃; for 0.5h; Inert atmosphere; Glovebox; Stage #2: With caesium carbonate In 1,4-dioxane at 40℃; Inert atmosphere; Glovebox; | 97% |
Stage #1: cyclohexenone; p-tert-butylphenylboronic acid With chlorobis(ethylene)rhodium(I) dimer; (R)-N-cinnamyl-2-methyl-N-phenylpropane-2-sulfinamide In 1,4-dioxane at 40℃; for 0.5h; Inert atmosphere; Stage #2: With potassium phosphate In 1,4-dioxane at 40℃; for 3h; Inert atmosphere; enantioselective reaction; | 89% |
2-(5-bromo-pyridin-3-yl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester
4-tert-butylphenylboronic acid
2-[5-(4-tert-butyl-phenyl)-pyridin-3-yl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 110℃; for 1h; Suzuki Coupling; Microwave irradiation; | 99% |
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 110℃; for 1h; microwave irradiation; | 99% |
4-bromobenzenecarbonitrile
4-tert-butylphenylboronic acid
4'-tert-butyl-biphenyl-4-carbonitrile
Conditions | Yield |
---|---|
With potassium carbonate; palladium dichloride In ethanol; water at 20℃; for 0.0833333h; Suzuki cross-coupling; | 99% |
With 4C27H21N9O6*12NO3(1-)*6Pd(2+)*6C12H10; potassium carbonate In ethanol; water at 55℃; for 10h; Suzuki-Miyaura Coupling; | 95% |
With potassium carbonate In ethyl acetate at 90℃; for 1.5h; Catalytic behavior; Suzuki-Miyaura Coupling; | 95% |
4-tert-butylphenylboronic acid
trifluoromethanesulfonic acid 4-formylnaphthalen-1-yl ester
4-(4-(t-butyl)phenyl)-1-naphthaldehyde
Conditions | Yield |
---|---|
With potassium carbonate; palladium diacetate; XPhos In water; acetonitrile at 90℃; for 6h; Suzuki Coupling; Inert atmosphere; | 99% |
With palladium diacetate; potassium carbonate; XPhos In 1,4-dioxane; water at 100℃; for 1h; Suzuki Coupling; | 88% |
1-bromo-2,3-dimethoxy-5-nitronaphthalene
4-tert-butylphenylboronic acid
1-(4-(t-butyl)phenyl)-2,3-dimethoxy-5-nitronaphthalene
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; acetonitrile at 100℃; Suzuki Coupling; | 99% |
5-([1,3]dioxolo[4,5-g]quinolin-7-yl)-2,3-dimethoxyphenyl trifluoromethanesulfonate
4-tert-butylphenylboronic acid
C28H27NO4
Conditions | Yield |
---|---|
With potassium carbonate; palladium diacetate; XPhos In water; acetonitrile at 90℃; for 3h; Suzuki Coupling; Inert atmosphere; | 99% |
The Molecular Structure of 4-tert-Butylphenylboronic acid (CAS NO.123324-71-0):
Empirical Formula: C10H15BO2
Molecular Weight: 178.0359
IUPAC Name: (4-tert-butylphenyl)boronic acid
Appearance: white to off-white crystalline powder
Nominal Mass: 178 Da
Average Mass: 178.0359 Da
Monoisotopic Mass: 178.116511 Da
Index of Refraction: 1.51
Molar Refractivity: 51.81 cm3
Molar Volume: 173 cm3
Surface Tension: 36.9 dyne/cm
Density: 1.02 g/cm3
Flash Point: 133.2 °C
Enthalpy of Vaporization: 56.66 kJ/mol
Boiling Point: 296.7 °C at 760 mmHg
Vapour Pressure: 0.000636 mmHg at 25°C
4-T-butylphenylboronic acid (123324-71-0) can be used as organic reagents,harmaceutical intermediates.
Hazard Codes: XiXn
Risk Statements: 36/37/38-22-20/21/22
R36/37/38: Irritating to eyes, respiratory system and skin
R22: Harmful if swallowed
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed
Safety Statements: 37/39-26-36
S37/39: Wear suitable gloves and eye/face protection
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36: Wear suitable protective clothing
WGK Germany: 3
Hazard Note: Irritant
HazardClass: IRRITANT
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