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123324-71-0 Usage

Chemical Properties

white to off-white crystalline powder

Uses

Different sources of media describe the Uses of 123324-71-0 differently. You can refer to the following data:
1. suzuki reaction
2. 4-t-Butylphenylboronic acid is a cross-coupling building block used in the preparation of tetracyclnes and tetracycline derivatives.
3. Cross-coupling building block used in synthesis of tetracycline derivatives.

Check Digit Verification of cas no

The CAS Registry Mumber 123324-71-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,3,3,2 and 4 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 123324-71:
(8*1)+(7*2)+(6*3)+(5*3)+(4*2)+(3*4)+(2*7)+(1*1)=90
90 % 10 = 0
So 123324-71-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H7BO4/c9-8(10)5-1-2-6-7(3-5)12-4-11-6/h1-3,9-10H,4H2

123324-71-0 Well-known Company Product Price

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  • TCI America

  • (B2251)  4-tert-Butylphenylboronic Acid (contains varying amounts of Anhydride)  

  • 123324-71-0

  • 5g

  • 202.00CNY

  • Detail
  • TCI America

  • (B2251)  4-tert-Butylphenylboronic Acid (contains varying amounts of Anhydride)  

  • 123324-71-0

  • 25g

  • 685.00CNY

  • Detail
  • Alfa Aesar

  • (B24408)  4-tert-Butylbenzeneboronic acid, 97%   

  • 123324-71-0

  • 1g

  • 216.0CNY

  • Detail
  • Alfa Aesar

  • (B24408)  4-tert-Butylbenzeneboronic acid, 97%   

  • 123324-71-0

  • 5g

  • 651.0CNY

  • Detail

123324-71-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-tert-Butylphenylboronic acid

1.2 Other means of identification

Product number -
Other names (4-tert-butylphenyl)boronic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:123324-71-0 SDS

123324-71-0Synthetic route

1-bromo-4-tert-butylbenzene
3972-65-4

1-bromo-4-tert-butylbenzene

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

Conditions
ConditionsYield
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
7732-18-5

water

potassium (4-tert-butyl)phenyltrifluoroborate

potassium (4-tert-butyl)phenyltrifluoroborate

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

Conditions
ConditionsYield
With 1H-imidazole; iron(III) chloride at 20℃; for 0.25h; Inert atmosphere;85%
Trimethyl borate
121-43-7

Trimethyl borate

1-bromo-4-tert-butylbenzene
3972-65-4

1-bromo-4-tert-butylbenzene

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

Conditions
ConditionsYield
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
688-74-4

boric acid tributyl ester

1-bromo-4-tert-butylbenzene
3972-65-4

1-bromo-4-tert-butylbenzene

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

Conditions
ConditionsYield
With sulfuric acid; magnesium In diethyl ether; water10%
tert-butylbenzene
253185-03-4, 253185-04-5

tert-butylbenzene

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

Conditions
ConditionsYield
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
1092730-06-7

4-tert-butylphenylboronic dimethyl ester

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

Conditions
ConditionsYield
With hydrogenchloride; water In tetrahydrofuran; hexane at 20℃; pH=3 - 5;
C20H25BO2

C20H25BO2

A

4-tert-Butylcatechol
98-29-3

4-tert-Butylcatechol

B

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

Conditions
ConditionsYield
In chloroform-d1 at 25℃; Equilibrium constant; Sealed tube;
C20H27BN2

C20H27BN2

A

4-(tert-butyl)-1,2-diaminobenzene
68176-57-8

4-(tert-butyl)-1,2-diaminobenzene

B

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

Conditions
ConditionsYield
In chloroform-d1 at 25℃; Equilibrium constant; Sealed tube;
tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

1-bromo-4-tert-butylbenzene
3972-65-4

1-bromo-4-tert-butylbenzene

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

Conditions
ConditionsYield
With potassium tert-butylate In methanol at 0 - 20℃;
4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

4-tert-butylphenylboronic acid sodium hydroxide salt

4-tert-butylphenylboronic acid sodium hydroxide salt

Conditions
ConditionsYield
With sodium hydroxide In toluene100%
ethyl 2-iodobenzoate
1829-28-3

ethyl 2-iodobenzoate

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

4'-tert-butylbiphenyl-2-carboxylic acid ethyl ester
863492-39-1

4'-tert-butylbiphenyl-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
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
922500-95-6

3-(nitromethylene)oxetane

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

3-(4-tert-butylphenyl)-3-(nitromethyl)oxetane
1221819-55-1

3-(4-tert-butylphenyl)-3-(nitromethyl)oxetane

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; water; potassium hydroxide In 1,4-dioxane at 20℃; for 2h;100%
para-bromotoluene
106-38-7

para-bromotoluene

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

1-(4-tert-butylphenyl)-4-methylbenzene

1-(4-tert-butylphenyl)-4-methylbenzene

Conditions
ConditionsYield
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
123324-71-0

4-tert-butylphenylboronic acid

para-tert-butylphenol
98-54-4

para-tert-butylphenol

Conditions
ConditionsYield
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
1147270-21-0

7-chloro-2-cyclohexylmethylindan-1-one

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

7-(4'-tert-butylphenyl)-2-cyclohexylmethylindan-1-one
1147270-22-1

7-(4'-tert-butylphenyl)-2-cyclohexylmethylindan-1-one

Conditions
ConditionsYield
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
1147270-30-1

7-chloro-2-(2,2-dimethylpropyl)indan-1-one

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

7-(4'-tert-butylphenyl)-2-(2,2-dimethylpropyl)indan-1-one
1147270-31-2

7-(4'-tert-butylphenyl)-2-(2,2-dimethylpropyl)indan-1-one

Conditions
ConditionsYield
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-(1-adamantylmethyl)-indan-1-one

7-chloro-2-(1-adamantylmethyl)-indan-1-one

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

7-(4'-tert-butyl-phenyl)-2-(1-adamantylmethyl)-indan-1-one

7-(4'-tert-butyl-phenyl)-2-(1-adamantylmethyl)-indan-1-one

Conditions
ConditionsYield
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
1446863-36-0

8-methyl-1,5-naphthyridin-4-yl trifluoromethanesulfonate

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

4-(4-(tert-butyl)phenyl)-8-methyl-1,5-naphthyridine
1446863-38-2

4-(4-(tert-butyl)phenyl)-8-methyl-1,5-naphthyridine

Conditions
ConditionsYield
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
610-97-9

o-iodo-methyl-benzoic acid

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

methyl 4′-(tert butyl)-[1,1′-biphenyl]-2-carboxylate
1528793-37-4

methyl 4′-(tert butyl)-[1,1′-biphenyl]-2-carboxylate

Conditions
ConditionsYield
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;
3-methoxy-thiophene
17573-92-1

3-methoxy-thiophene

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

C15H18OS

C15H18OS

Conditions
ConditionsYield
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;
1-((1R,2R,3S,4S)-2,3-dihydroxy-1,2,3,4-tetrahydro-1,4-epiminonaphthalen-9-yl)-3-(4-(triisopropylsilyl)-1H-1,2,3-triazol-1-yl)propan-1-one

1-((1R,2R,3S,4S)-2,3-dihydroxy-1,2,3,4-tetrahydro-1,4-epiminonaphthalen-9-yl)-3-(4-(triisopropylsilyl)-1H-1,2,3-triazol-1-yl)propan-1-one

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

1-((4R,9S,9aS)-2-(4-(tert-butyl)phenyl)-3a,4,9,9a-tetrahydro-4,9-epiminonaphtho[2,3-d][1,3,2]dioxaborol-10-yl)-3-(4-(triisopropylsilyl)-1H-1,2,3-triazol-1-yl)propan-1-one

1-((4R,9S,9aS)-2-(4-(tert-butyl)phenyl)-3a,4,9,9a-tetrahydro-4,9-epiminonaphtho[2,3-d][1,3,2]dioxaborol-10-yl)-3-(4-(triisopropylsilyl)-1H-1,2,3-triazol-1-yl)propan-1-one

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.166667h;100%
7-chloro-2-(1-adamantylmethyl)indan-1-one
1147270-34-5

7-chloro-2-(1-adamantylmethyl)indan-1-one

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

7-(4'-tert-butylphenyl)-2-(1-adamantylmethyl)indan-1-one
1147270-35-6

7-(4'-tert-butylphenyl)-2-(1-adamantylmethyl)indan-1-one

Conditions
ConditionsYield
With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate In water at 125℃; for 6h; Inert atmosphere;100%
C21H18BrNOS

C21H18BrNOS

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

C31H31NOS

C31H31NOS

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 80℃; for 24h;100%
bromobenzene
108-86-1

bromobenzene

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

4-tert-butylbiphenyl
1625-92-9

4-tert-butylbiphenyl

Conditions
ConditionsYield
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
930-68-7

cyclohexenone

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

(R)-3-(4-(tert-butyl)phenyl)cyclohexan-1-one
846606-25-5

(R)-3-(4-(tert-butyl)phenyl)cyclohexan-1-one

Conditions
ConditionsYield
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
123324-71-0

4-tert-butylphenylboronic acid

4,4'-di-tert-butylbiphenyl
1625-91-8

4,4'-di-tert-butylbiphenyl

Conditions
ConditionsYield
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
104-92-7

1-bromo-4-methoxy-benzene

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

4-tert-butyl-4'-methoxylbiphenyl

4-tert-butyl-4'-methoxylbiphenyl

Conditions
ConditionsYield
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
614-76-6

N-acetyl-2-bromoaniline

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

N-(4'-(tert-butyl)-[1,1'-biphenyl]-2-yl)acetamide

N-(4'-(tert-butyl)-[1,1'-biphenyl]-2-yl)acetamide

Conditions
ConditionsYield
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
906067-45-6

(4-bromophenyl)-(9H-β-carbolin-1-yl)-methanone

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

C28H24N2O
922525-74-4

C28H24N2O

Conditions
ConditionsYield
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
906067-46-7

(3-bromophenyl)-(9H-β-carbolin-1-yl)-methanone

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

C28H24N2O
922525-73-3

C28H24N2O

Conditions
ConditionsYield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene at 90℃; for 24h; Suzuki-Miyaura coupling;99%
4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

phenylacetylene
536-74-3

phenylacetylene

[(4-tert-butylphenyl)ethynyl]benzene
29778-26-5

[(4-tert-butylphenyl)ethynyl]benzene

Conditions
ConditionsYield
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%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

2-(4-tert-butylphenyl)pyridine

2-(4-tert-butylphenyl)pyridine

Conditions
ConditionsYield
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
3179-10-0

1-methoxy-4-(2-nitro-vinyl)-benzene

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

1-(1-(4-tert-butylphenyl)-2-nitroethyl)-4-methoxybenzene

1-(1-(4-tert-butylphenyl)-2-nitroethyl)-4-methoxybenzene

Conditions
ConditionsYield
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
930-68-7

cyclohexenone

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

(S)-3-(4-(tert-butyl)phenyl)cyclohexanone
141632-33-9

(S)-3-(4-(tert-butyl)phenyl)cyclohexanone

Conditions
ConditionsYield
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
1343455-35-5

2-(5-bromo-pyridin-3-yl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester

4-tert-butylphenylboronic acid
123324-71-0

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
1343455-37-7

2-[5-(4-tert-butyl-phenyl)-pyridin-3-yl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester

Conditions
ConditionsYield
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
623-00-7

4-bromobenzenecarbonitrile

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

4'-tert-butyl-biphenyl-4-carbonitrile
192699-51-7

4'-tert-butyl-biphenyl-4-carbonitrile

Conditions
ConditionsYield
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
123324-71-0

4-tert-butylphenylboronic acid

trifluoromethanesulfonic acid 4-formylnaphthalen-1-yl ester
219685-17-3

trifluoromethanesulfonic acid 4-formylnaphthalen-1-yl ester

4-(4-(t-butyl)phenyl)-1-naphthaldehyde
1353555-90-4

4-(4-(t-butyl)phenyl)-1-naphthaldehyde

Conditions
ConditionsYield
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
1235871-28-9

1-bromo-2,3-dimethoxy-5-nitronaphthalene

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

1-(4-(t-butyl)phenyl)-2,3-dimethoxy-5-nitronaphthalene
1353556-07-6

1-(4-(t-butyl)phenyl)-2,3-dimethoxy-5-nitronaphthalene

Conditions
ConditionsYield
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
1353555-71-1

5-([1,3]dioxolo[4,5-g]quinolin-7-yl)-2,3-dimethoxyphenyl trifluoromethanesulfonate

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

C28H27NO4
1353554-65-0

C28H27NO4

Conditions
ConditionsYield
With potassium carbonate; palladium diacetate; XPhos In water; acetonitrile at 90℃; for 3h; Suzuki Coupling; Inert atmosphere;99%

123324-71-0Relevant articles and documents

Synthesis of t-butylated diphenylanthracene derivatives as blue host materials for OLED applications

Balaganesan, Banumathy,Shen, Wen-Jian,Chen, Chin H.

, p. 5747 - 5750 (2003)

This paper describes the cost-effective synthesis and the photoluminescence of diphenylanthracene derivatives, which are found to be potential blue host materials for organic light emitting diode (OLED) technology.

Spectroscopic and computational investigations of the thermodynamics of boronate ester and diazaborole self-assembly

Goldberg, Alexander R.,Northrop, Brian H.

, p. 969 - 980 (2016)

The solution phase self-assembly of boronate esters, diazaboroles, oxathiaboroles, and dithiaboroles from the condensation of arylboronic acids with aromatic diol, diamine, hydroxythiol, and dithiol compounds in chloroform has been investigated by 1H NMR spectroscopy and computational methods. Six arylboronic acids were included in the investigations with each boronic acid varying in the substituent at its 4-position. Both computational and experimental results show that the para-substituent of the arylboronic acid does not significantly influence the favorability of forming a condensation product with a given organic donor. The type of donor, however, greatly influences the favorability of self-assembly. 1H NMR spectroscopy indicates that condensation reactions between arylboronic acids and catechol to give boronate esters are the most favored thermodynamically, followed by diazaborole formation. Computational investigations support this conclusion. Neither oxathiaboroles nor dithiaboroles form spontaneously at equilibrium in chloroform at room temperature. Computational results suggest that the effect of borylation on the frontier orbitals of each donor helps to explain differences in the favorability of their condensation reactions with arylboronic acids. The results can inform the use of boronic acids as they are increasingly utilized in the dynamic self-assembly of organic materials and as components in dynamic combinatorial libraries.

Iron catalysis and water: A synergy for refunctionalization of boron

Wood, John L.,Marciasini, Ludovic D.,Vaultier, Michel,Pucheault, Mathieu

supporting information, p. 551 - 555 (2014/03/21)

A new catalytic system has been optimized to promote the conversion of boron species into others. FeCl3 associated with imidazole and water favors boron refunctionalization under mild conditions. Georg Thieme Verlag Stuttgart New York.

Vaulted biaryls in catalysis: A structure-activity relationship guided tour of the immanent domain of the VANOL ligand

Guan, Yong,Ding, Zhensheng,Wulff, William D.

, p. 15565 - 15571 (2013/11/19)

The active site in the BOROX catalyst is a chiral polyborate anion (boroxinate) that is assembled in situ from three equivalents of B(OPh) 3 and one of the VANOL ligand by a molecule of substrate. The substrates are bound to the boroxinate by Hbonds to oxygen atoms O1-O3. The effects of introducing substituents at each position of the naphthalene core of the VANOL ligand are systematically investigated in an aziridination reaction. Substituents in the 4,4′- and 8,8′-positions have a negative effect on catalyst performance, whereas, substituents in the 7- and 7′-positions have the biggest impact in a positive direction. VANOL destination: The active site in the BOROX catalyst is a chiral polyborate anion (boroxinate; see figure) that is assembled in situ from three equivalents of B(OPh)3 and one of the VANOL ligand by a molecule of substrate. The effects of introducing substituents at each position of the naphthalene core of the VANOL ligand are systematically investigated in an aziridination reaction. Copyright

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