Product Name

  • Name

    (4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZENE

  • EINECS
  • CAS No. 24388-23-6
  • Article Data317
  • CAS DataBase
  • Density 0.99 g/cm3
  • Solubility
  • Melting Point 27-31 °C(lit.)
  • Formula C12H17BO2
  • Boiling Point 282.058 °C at 760 mmHg
  • Molecular Weight 204.077
  • Flash Point 124.384 °C
  • Transport Information
  • Appearance
  • Safety 26-36
  • Risk Codes 22-36/37/38
  • Molecular Structure Molecular Structure of 24388-23-6 ((4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZENE)
  • Hazard Symbols IrritantXi,HarmfulXn
  • Synonyms Benzeneboronicacid, cyclic tetramethylethylene ester (7CI,8CI);2,3-Butanediol,2,3-dimethyl-, cyclic benzeneboronate (8CI);(Pinacolboryl)benzene;2-Phenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;Phenylboronic acid pinacolester;Pinacol phenylboronate;Phenylboronic acid pinacol ester;
  • PSA 18.46000
  • LogP 1.98580

Synthetic route

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

benzene
71-43-2

benzene

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
[Ir(COD)(1,3-dicyclohexylimidazolidin-2-ylidene)2]CF3CO2 at 40℃; for 10h;100%
(η4-1,5-cyclooctadiene)bis(1,3-dimethylimidazolin-2-ylidene)iridium(I) trifluoracetate In benzene (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(C3H2N2Me2)2(CF3CO2) in benzene; stirring and heating at 40°C for 12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2;100%
(η4-1,5-cyclooctadiene)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)iridium(I) trifluoroacetate In benzene (N2); using Schlenk techniques; dissolving of 2 mmol pinacolborane and 1.5 mol% of Ir(COD)(1,1'-dimethyl-3,3'-o-xylylene-diimidazolin-2,2'-diylidene)2(CF3CO2) in benzene; stirring and heating at 40°C for 12 h; monitoring by GC-MS; removal of solvent under vac. at room temp.; chromy. over silica gel, eluting with CH2Cl2;100%
bromobenzene
108-86-1

bromobenzene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 85℃; for 6h; Inert atmosphere;100%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride In methanol at 20℃; for 8h;92%
Stage #1: bromobenzene; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With bis(trifluoromethane)sulfonimide lithium In tetrahydrofuran at 20℃; Electrochemical reaction;
Stage #2: With sulfuric acid at 0℃; pH=5; Further stages.;		78%
bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

benzene
71-43-2

benzene

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With [Ir(COD)(OMe)]2-Covalent organic framework (4-iPr) at 100℃; for 24h; Reagent/catalyst; Inert atmosphere;100%
With iridium-1,5-cyclooctadiene complex immobilized 2,2'-bipyridine-functionalized organosilica nanotubes at 80℃; for 12h; Catalytic behavior; Kinetics; Reagent/catalyst; Inert atmosphere;97%
With [Ir(OMe)(1,5-cyclooctadiene)]2 In benzene at 80℃; for 12h; Kinetics; Reagent/catalyst; Schlenk technique; Inert atmosphere;94%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

phenylboronic acid
98-80-6

phenylboronic acid

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
at 0℃; for 1h;100%
In pentane at 0 - 20℃; for 3h;100%
In tetrahydrofuran at 20℃; for 1h;95%
chlorobenzene
108-90-7

chlorobenzene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; triphenylphosphine; bis(1,5-cyclooctadiene)nickel (0) In methanol at 20 - 50℃; Product distribution / selectivity; Inert atmosphere;99%
With N-ethyl-N,N-diisopropylamine; triphenylphosphine; (1,5-cyclooctadiene)(cyclopentadienyl)nickel In methanol at 20 - 50℃; for 25h; Product distribution / selectivity; Inert atmosphere;99%
With sodium acetate; bis(dibenzylideneacetone)-palladium(0); XPhos for 12h; Reagent/catalyst; Miyaura Borylation Reaction; Heating;99%
bromobenzene
108-86-1

bromobenzene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With DPEPhos; sodium acetate; bis(dibenzylideneacetone)-palladium(0) for 12h; Reagent/catalyst; Miyaura Borylation Reaction; Heating;99%
With Co(1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene)2Cl2; potassium methanolate In tert-butyl methyl ether at 50℃; for 8h;95%
With C37H51ClFeNPPd; potassium acetate In 1,4-dioxane at 80℃; for 3h; Suzuki-Miyaura coupling; Inert atmosphere;93%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

potassium phenyltrifluoborate

potassium phenyltrifluoborate

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With chloro-trimethyl-silane; potassium carbonate In acetonitrile at 20℃; for 2h;97%
With montmorillonite K10 In tetrahydrofuran at 25℃; Solvent; Reagent/catalyst; Molecular sieve;97%
With 1H-imidazole; iron(III) chloride In water at 20℃; for 0.25h; Inert atmosphere;65%
iPr(PNP)*Rh(Ph)

iPr(PNP)*Rh(Ph)

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

C25H47BNO2P2Rh(1+)

C25H47BNO2P2Rh(1+)

Conditions
ConditionsYield
In benzene-d6 at 150℃; for 4h; Sealed tube; Inert atmosphere;A 97%
B 93%
...Expand
iodobenzene
591-50-4

iodobenzene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With (C2H5)3N; [Pd(2,6-bis(2,5-diphenylphospholyl-1-methyl)pyridine)Cl][BF4] In 1,4-dioxane (N2 or Ar); heated at 80°C for 48 h; evapd., Et2O added, filtered, washed (ether), evapd., chromd. (hexanes/Et3N-treated silica gel, hexanes);96%
With triethylamine; bis(diphosphaferrocene)PdCl2 dimer In 1,4-dioxane at 80℃; for 144h;95%
With triethylamine; ς4,λ5-phosphinine palladium In 1,4-dioxane; toluene at 80℃; for 15h; Myaura cross-coupling reaction;95%
benzenediazonium tetrafluoroborate
369-57-3

benzenediazonium tetrafluoroborate

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In methanol at 20 - 40℃; for 3h; Condensation;96%
With 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; palladium diacetate In tetrahydrofuran at 20℃; for 1.5h;87%
With zinc(II) perchlorate In methanol at 40℃; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere;80%
phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
In tetrahydrofuran at 25℃; for 1h; Inert atmosphere;96%
1-benzoylpyrrolidine-2,5-dione
6343-27-7

1-benzoylpyrrolidine-2,5-dione

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With Wilkinson's catalyst In toluene at 160℃; for 15h; Inert atmosphere;96%
bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

benzene
71-43-2

benzene

A

benzene-1,4-diboronic acid bispinacol ester
99770-93-1

benzene-1,4-diboronic acid bispinacol ester

B

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)diiridium(I) dichloride In neat (no solvent) at 80°C for 16 h;A 1%
B 95%
...Expand
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;95%
benzoic acid
65-85-0

benzoic acid

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With palladium diacetate; 2,2-dimethylpropanoic anhydride; triethylamine; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Catalytic behavior; Reagent/catalyst;95%
With palladium diacetate; 2,2-dimethylpropanoic anhydride; triethylamine; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h;95%
With biphenyl; naphthalene-1,4-dicarbonitrile In water; acetonitrile at 30℃; for 6h; Wavelength; Inert atmosphere; UV-irradiation;55%
4-cyanophenylboronic acid pinacol ester
171364-82-2

4-cyanophenylboronic acid pinacol ester

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tri-n-butyl phosphite; chlorotriisopropylsilane In ethyl-cyclohexane at 130℃; for 15h; Inert atmosphere;94%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tri-n-butyl phosphite; chlorotriisopropylsilane In ethylcyclohexane at 130℃; for 15h; Inert atmosphere;94%
iodobenzene
591-50-4

iodobenzene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; triphenylphosphine; bis(1,5-cyclooctadiene)nickel (0) In methanol at 20 - 30℃; Inert atmosphere;93%
With N-ethyl-N,N-diisopropylamine; triphenylphosphine; (1,5-cyclooctadiene)(cyclopentadienyl)nickel In methanol at 20 - 30℃; for 21h; Product distribution / selectivity; Inert atmosphere;93%
In acetonitrile at 15℃; for 4h; Microwave irradiation;90%
bromobenzene
108-86-1

bromobenzene

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran; hexane at 24℃; for 0.000861111h;
Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at 24℃; for 0.0025h;		92%
Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran at -78 - -40℃;
Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran		90%
Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran		87%
2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
73852-88-7

2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline bis[(2-diphenyl-phosphino)phenyl]ether copper(I) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 16h; Inert atmosphere; Sealed tube; Irradiation;92%
With 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline bis[(2-diphenyl-phosphino)phenyl]ether copper(I) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 16h; UV-irradiation;92%
With tetraethylammonium perchlorate; triethylamine In dimethyl sulfoxide at 20℃; for 12h; Electrolysis; Green chemistry;79%
fluorobenzene
462-06-6

fluorobenzene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); copper(l) iodide; cesium fluoride; tricyclohexylphosphine In toluene at 80℃; for 24h; Inert atmosphere;91%
With tetramethylammonium fluoride; 2-mercaptopyridine sodium salt In acetonitrile at 30 - 35℃; for 24h; Reagent/catalyst; Irradiation; Inert atmosphere;78%
With chlorobis(tricyclohexylphosphine)copper(I); cesium fluoride In toluene at 80℃; for 24h;71%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

diisopropylamine borane
55124-35-1

diisopropylamine borane

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
Stage #1: diisopropylamine borane; phenylmagnesium bromide In tetrahydrofuran at 20℃;
Stage #2: With methanol In tetrahydrofuran
Stage #3: 2,3-dimethyl-2,3-butane diol In tetrahydrofuran		91%
...Expand
benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With 2,2'-azobis(N-cyclohexyl-2-methylpropionamidine) dihydrochloride In water at 80℃; for 8h; Temperature; Reagent/catalyst;90.8%
With 2,2'-azobis(2-methylpropionamidine) dihydrochloride In water at 50℃; for 10h; Temperature; Reagent/catalyst;88.1%
With dipotassium hydrogenphosphate In acetonitrile at 20℃; for 24h; UV-irradiation;65%
bromobenzene
108-86-1

bromobenzene

para-fluorostyrene
405-99-2

para-fluorostyrene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

2-(2-(4-fluorophenyl)-2-phenylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1609554-37-1

2-(2-(4-fluorophenyl)-2-phenylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

B

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With (1,3-dimesitylimidazolidin-2-yl)copper(I) chloride; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); sodium t-butanolate In toluene at 22℃; for 6h; Glovebox; Inert atmosphere;A 90%
B 8%
...Expand
bromobenzene
108-86-1

bromobenzene

1-methyl-2-vinyl-benzene
611-15-4

1-methyl-2-vinyl-benzene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-o-tolylethyl]benzene

[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-o-tolylethyl]benzene

B

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With (1,3-dimesitylimidazolidin-2-yl)copper(I) chloride; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); sodium t-butanolate In toluene at 22℃; for 6h; Glovebox; Inert atmosphere;A 90%
B 5.5%
...Expand
1-(benzoyl)piperidine-2,6-dione

1-(benzoyl)piperidine-2,6-dione

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With Wilkinson's catalyst In toluene at 160℃; for 15h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere;90%
aniline
62-53-3

aniline

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With tert.-butylnitrite; eosin In acetonitrile at 20℃; for 2h; Irradiation;88%
With tert-butyl nitrite; benzoyl peroxide In acetonitrile aniline (1 mmol), B2pin2, tBuONO (in 1:1.1:1.5 molar ratio) and 2,2'-azobisisobutyronitrile (2 mol%) mixed in MeCN, stirred at room temp. for 3 h; soln. concd. (under reduced pressure), residue chromd.;77%
With tert-butyl nitrite; benzoyl peroxide In acetonitrile aniline (1 mmol), B2pin2, tBuONO (in 1:1.1:1.5 molar ratio) and 2,2'-azobisisobutyronitrile (5 mol%) mixed in MeCN, stirred at room temp. for 3 h; soln. concd. (under reduced pressure), residue chromd.;70%
3,3-diethyl-1-phenyltriaz-1-ene
13056-98-9

3,3-diethyl-1-phenyltriaz-1-ene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With zinc(II) perchlorate; trifluorormethanesulfonic acid In methanol at 60℃;88%
phenyltrimethylammonium iodide
98-04-4

phenyltrimethylammonium iodide

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
With 10H-phenothiazine; caesium carbonate In acetonitrile for 18h; Wavelength; Irradiation; Sealed tube; Inert atmosphere;88%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

2-phenyl[1,3,2]dioxaborolane
4406-72-8

2-phenyl[1,3,2]dioxaborolane

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

Conditions
ConditionsYield
In chloroform-d1 Kinetics; byproducts: HOCH2CH2OH; inder inert atm., at 25°C, for 94 h, in NMR tube; monitoring by (1)H NMR;87.8%
In chloroform-d1 at 25℃; for 94h; Product distribution; Further Variations:; Reaction partners; reaction time;
With boron trifluoride diethyl etherate In chloroform-d1 at 20℃; Reagent/catalyst;
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

phenylboronic acid
98-80-6

phenylboronic acid

Conditions
ConditionsYield
Stage #1: 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole With potassium hydrogen difluoride In methanol at 20℃; for 0.25h;
Stage #2: With lithium hydroxide In acetonitrile at 20℃; for 20h;		100%
With hydrogenchloride In water at 20℃; for 15h;100%
With polystyrene boronic acid; trifluoroacetic acid In acetonitrile for 18h; Heating;98%
Multi-step reaction with 2 steps
1: diethyl ether / 0.5 h / 20 °C
2: hydrogenchloride / water / 0.33 h
View Scheme
With dimyristoylphosphatidylcholine; water In dimethyl sulfoxide at 20℃; for 168h;
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

phenol
108-95-2

phenol

Conditions
ConditionsYield
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%
(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-21-iodo-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4, 6,10,18-pentaen-9-yl carbamate
75747-28-3

(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-21-iodo-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4, 6,10,18-pentaen-9-yl carbamate

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-8,14,19-trimethoxy-10,12,16,21-pentamethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4, 6,10,18-pentaen-9-yl carbamate
1427296-91-0

(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-8,14,19-trimethoxy-10,12,16,21-pentamethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4, 6,10,18-pentaen-9-yl carbamate

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; cesium fluoride In 1,4-dioxane; water at 40℃; for 16h; Inert atmosphere;100%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; cesium fluoride In 1,4-dioxane; water at 40℃; for 16h; Suzuki-Miyaura Coupling;100%
3,6-dibromo-9,10-bis(octyloxy)phenanthrene
1425053-94-6

3,6-dibromo-9,10-bis(octyloxy)phenanthrene

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

C42H50O2

C42H50O2

Conditions
ConditionsYield
With bis(tri-t-butylphosphine)palladium(0); potassium carbonate In tetrahydrofuran; water Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;100%
(4-chloro-phenyl)-acetic acid methyl ester
52449-43-1

(4-chloro-phenyl)-acetic acid methyl ester

C10H8BBrNO4

C10H8BBrNO4

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
144432-80-4

2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In tetrahydrofuran; water at 90℃; for 24h; Suzuki-Miyaura Coupling; chemoselective reaction;100%
...Expand
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

2,6-dichloro-3-iodopyrazine
136866-30-3

2,6-dichloro-3-iodopyrazine

2,6-dichloro-3-phenylpyrazine
64163-11-7

2,6-dichloro-3-phenylpyrazine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In water; toluene at 100℃; for 15h; Inert atmosphere;100%
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

4-bromo-3,5-diisopropyl-1-(p-toluenesulfonyl)pyrazole

4-bromo-3,5-diisopropyl-1-(p-toluenesulfonyl)pyrazole

A

biphenyl
92-52-4

biphenyl

B

4-phenyl-3,5-diisopropyl-1-(p-toluenesulfonyl)pyrazole

4-phenyl-3,5-diisopropyl-1-(p-toluenesulfonyl)pyrazole

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Reflux;A 45%
B 100%
...Expand
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

ethyl 2-(4-bromo-2-fluorophenyl)-7-chloropyrazolo[1,5-a]pyrimidine-5-carboxylate

ethyl 2-(4-bromo-2-fluorophenyl)-7-chloropyrazolo[1,5-a]pyrimidine-5-carboxylate

ethyl 2-(4-bromo-2-fluorophenyl)-7-phenylpyrazolo[1,5-a]pyrimidine-5-carboxylate

ethyl 2-(4-bromo-2-fluorophenyl)-7-phenylpyrazolo[1,5-a]pyrimidine-5-carboxylate

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In tetrahydrofuran; water at 70℃; for 18h; Inert atmosphere;100%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In tetrahydrofuran; water at 70℃; for 4h; Inert atmosphere;
2-Iodothiophene
3437-95-4

2-Iodothiophene

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

2-phenylthiophene
825-55-8

2-phenylthiophene

Conditions
ConditionsYield
With potassium carbonate In methanol at 60℃; for 1h; Suzuki-Miyaura Coupling;99.8%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

4-methoxylbiphenyl
613-37-6

4-methoxylbiphenyl

Conditions
ConditionsYield
With potassium carbonate In water at 20℃; for 6h; Reagent/catalyst; Solvent; Time; Concentration; Suzuki-Miyaura Coupling;99%
With sodium phosphate; palladium on activated charcoal In water; isopropyl alcohol at 20℃; for 24h; Suzuki-Miyaura cross-coupling;96%
With trans-dichlorido-(1,3-bis(2-ethoxy-2-oxopropyl)-imidazol-2-ylidine)(pyridine)palladium(II); tetrabutylammomium bromide; potassium carbonate In water at 60℃; for 24h; Suzuki-Miyaura Coupling;87%
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

para-bromoacetophenone
99-90-1

para-bromoacetophenone

biphenyl-4-acetaldehyde
92-91-1

biphenyl-4-acetaldehyde

Conditions
ConditionsYield
With caesium carbonate In methanol at 60℃; for 24h; Suzuki-Miyaura reaction; Inert atmosphere;99%
With potassium carbonate In water; N,N-dimethyl-formamide at 80℃; Suzuki-Miyaura cross-coupling reaction; Inert atmosphere;99%
With potassium phosphate; (C5H5FeC5H3C(CH3)NC6H4CH3)PdCl(tricyclohexylphosphine); potassium acetate In 1,4-dioxane; water at 100℃; for 3h; Suzuki coupling; Inert atmosphere;92%
cycloheptyl bromide
2404-35-5

cycloheptyl bromide

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

phenylcycloheptane
4401-18-7

phenylcycloheptane

Conditions
ConditionsYield
Stage #1: 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole With tert.-butyl lithium In tetrahydrofuran; pentane at -40 - 0℃; for 1h; Inert atmosphere;
Stage #2: cycloheptyl bromide With dichloro(1,2-{bis[3,5-bis(trimethylsilyl)pheny]phosphino-κP}benzene)iron(II); magnesium bromide In tetrahydrofuran at 0 - 40℃; Suzuki-Miyaura coupling; Inert atmosphere;		99%
With C25H33Cl2FeLiN2*0.75C4H8O; lithium ethylmethyl amide In benzene at 20℃; for 24h; Catalytic behavior; Reagent/catalyst; Concentration; Solvent; Suzuki-Miyaura Coupling; Glovebox; Inert atmosphere;95%
With 2,2-bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)acetonitrile; (2,2-bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)acetonitrile)FeCl; lithium ethylmethyl amide In benzene for 48.25h; Catalytic behavior; Reagent/catalyst; Solvent; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube;80%
3-Bromopyridine
626-55-1

3-Bromopyridine

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

3-phenylpyridine
1008-88-4

3-phenylpyridine

Conditions
ConditionsYield
With potassium carbonate In water at 20℃; for 6h; Suzuki-Miyaura Coupling;99%
With potassium carbonate In ethanol; water at 20℃; Suzuki-Miyaura Coupling; Green chemistry;85%
With potassium phosphate; (C5H5FeC5H3C(CH3)NC6H4CH3)PdCl(tricyclohexylphosphine); potassium acetate In 1,4-dioxane; water at 100℃; for 15h; Suzuki coupling; Inert atmosphere;78%
With palladium diacetate; caesium carbonate In methanol; toluene at 60℃; for 10h; Suzuki coupling;71%
With sodium carbonate In water at 120℃; for 0.5h; Irradiation;40 mg
chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I)

chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I)

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)phenylgold

(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)phenylgold

Conditions
ConditionsYield
With potassium hydroxide In toluene at 50℃; for 2h;99%
para-bromotoluene
106-38-7

para-bromotoluene

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

4-Methylbiphenyl
644-08-6

4-Methylbiphenyl

Conditions
ConditionsYield
With potassium carbonate In water at 20℃; for 6h; Suzuki-Miyaura Coupling;99%
With C17H36ClN6NiP2(1+)*Cl(1-) In toluene for 16h; Suzuki-Miyaura Coupling; Alkaline conditions; Inert atmosphere; Heating;97%
With hydrogenchloride; potassium carbonate In water; N,N-dimethyl-formamide at 95℃; pH=10.6; Suzuki-Miyaura Coupling; Inert atmosphere;
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In propan-1-ol; water at 100℃; for 0.5h; Temperature; Suzuki-Miyaura Coupling; Inert atmosphere;95 %Chromat.
3-Bromothiophene
872-31-1

3-Bromothiophene

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

3-phenylthiophene
2404-87-7

3-phenylthiophene

Conditions
ConditionsYield
With potassium carbonate In water at 20℃; for 6h; Suzuki-Miyaura Coupling;99%
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

4-Phenylbenzaldehyde
3218-36-8

4-Phenylbenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In water at 20℃; for 6h; Suzuki-Miyaura Coupling;99%
1-(m-tolyl)pyrazole
850380-23-3

1-(m-tolyl)pyrazole

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

1-(4-methyl[1,1'-biphenyl]-2-yl)-1H-pyrazole

1-(4-methyl[1,1'-biphenyl]-2-yl)-1H-pyrazole

Conditions
ConditionsYield
Stage #1: 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole With (2-methylpropyl)lithium In tetrahydrofuran; cyclohexane at -78 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: 1-(m-tolyl)pyrazole With iron(III)-acetylacetonate; ZnBr2*C6H16N2; cis-1,2-bis-(diphenylphosphino)ethene In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Inert atmosphere;
Stage #3: With 1,2-dichloro-2-methylpropane In tetrahydrofuran; cyclohexane at 30℃; Inert atmosphere;		99%
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

N-benzyl-N-(tert-butoxycarbonyl)-benzamide
85909-02-0

N-benzyl-N-(tert-butoxycarbonyl)-benzamide

benzophenone
119-61-9

benzophenone

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; water; 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene In toluene at 50℃; for 24h; Reagent/catalyst; Suzuki-Miyaura Coupling;99%
With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene In water; toluene at 50℃; for 24h; Reagent/catalyst; Temperature; Suzuki-Miyaura Coupling;96%
bromobenzene
108-86-1

bromobenzene

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

biphenyl
92-52-4

biphenyl

Conditions
ConditionsYield
With trans-dichlorido-(1,3-bis(2-ethoxy-2-oxopropyl)-imidazol-2-ylidine)(pyridine)palladium(II); tetrabutylammomium bromide; potassium carbonate In water at 60℃; for 24h; Suzuki-Miyaura Coupling;99%
With copper(ll) sulfate pentahydrate; C62H66N2O6; sodium citrate; sodium carbonate; potassium carbonate In ethanol; water at 20℃; for 8h; Suzuki-Miyaura Coupling; Irradiation; Green chemistry;72%
With caesium carbonate In water; N,N-dimethyl-formamide at 30℃; under 760.051 Torr; for 8h; Suzuki-Miyaura Coupling; Irradiation;62%
1-phenyl-3-phospholene 1-oxide
5186-73-2

1-phenyl-3-phospholene 1-oxide

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

(1S,3S)-1,3-diphenylphospholane 1-oxide

(1S,3S)-1,3-diphenylphospholane 1-oxide

Conditions
ConditionsYield
With chlorobis(cyclooctene)rhodium(I) dimer; potassium hydroxide; (R)-segphos In 1,4-dioxane; water at 25 - 80℃; for 16h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Sealed tube; stereoselective reaction;99%
1-phenyl-3-phospholene 1-oxide
5186-73-2

1-phenyl-3-phospholene 1-oxide

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

A

(1S,3S)-1,3-diphenylphospholane 1-oxide

(1S,3S)-1,3-diphenylphospholane 1-oxide

B

(1R,3R)-1,3-diphenylphospholane 1-oxide

(1R,3R)-1,3-diphenylphospholane 1-oxide

Conditions
ConditionsYield
With chlorobis(cyclooctene)rhodium(I) dimer; (R)-(+)-2,2'bis(diphenylphosphino)-1,1'-binaphthalene; potassium hydroxide In 1,4-dioxane; water at 80℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube; stereoselective reaction;A 99%
B n/a
...Expand
1-(4-(trifluoromethyl)phenyl)-3-phospholene-1-oxide

1-(4-(trifluoromethyl)phenyl)-3-phospholene-1-oxide

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

C17H16F3OP

C17H16F3OP

Conditions
ConditionsYield
With chlorobis(cyclooctene)rhodium(I) dimer; potassium hydroxide; (R)-segphos In 1,4-dioxane; water at 25 - 80℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube; stereoselective reaction;99%
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

tert-butyl (2-allyl-4-fluorobenzoyl)(benzyl)carbamate

tert-butyl (2-allyl-4-fluorobenzoyl)(benzyl)carbamate

2-benzyl-5-fluoro-2,3-dihydro-1H-inden-1-one
1376129-52-0

2-benzyl-5-fluoro-2,3-dihydro-1H-inden-1-one

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene In tetrahydrofuran; water at 60℃; Inert atmosphere;99%

(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene Specification

The 1,3,2-Dioxaborolane,4,4,5,5-tetramethyl-2-phenyl-, with the CAS registry number 24388-23-6, is also known as 2-Phenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. This chemical's molecular formula is C12H17BO2 and molecular weight is 204.07318. Its IUPAC name is called 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane.

Physical properties of 1,3,2-Dioxaborolane,4,4,5,5-tetramethyl-2-phenyl-: (1)#H bond acceptors: 2; (2)#Freely Rotating Bonds: 1; (3)Index of Refraction: 1.49; (4)Molar Refractivity: 59.45 cm3; (5)Molar Volume: 205.2 cm3; (6)Surface Tension: 30.3 dyne/cm; (7)Density: 0.99 g/cm3; (8)Flash Point: 124.4 °C; (9)Enthalpy of Vaporization: 50 kJ/mol; (10)Boiling Point: 282.1 °C at 760 mmHg; (11)Vapour Pressure: 0.00586 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause damage to health and may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2
(2)InChI: InChI=1S/C12H17BO2/c1-11(2)12(3,4)15-13(14-11)10-8-6-5-7-9-10/h5-9H,1-4H3
(3)InChIKey: KKLCYBZPQDOFQK-UHFFFAOYSA-N

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