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Cas Database |
| Name |
(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene |
EINECS | N/A |
| CAS No. | 24388-23-6 | Density | 0.99 g/cm3 |
| PSA | 18.46000 | LogP | 1.98580 |
| Solubility | N/A | 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 | N/A | Appearance | N/A |
| Safety | 26-36 | Risk Codes | 22-36/37/38 |
| Molecular Structure |
|
Hazard Symbols |
 Xi, Xn
|
| 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; |
Article Data | 317 |
(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene Synthetic route
- 25015-63-8
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
- 71-43-2
benzene
- 24388-23-6
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
| Conditions | Yield |
|---|---|
| [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% |
- 108-86-1
bromobenzene
- 25015-63-8
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
- 24388-23-6
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
| Conditions | Yield |
|---|---|
| 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% |
- 73183-34-3
bis(pinacol)diborane
- 71-43-2
benzene
- 24388-23-6
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
| Conditions | Yield |
|---|---|
| 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% |
- 76-09-5
2,3-dimethyl-2,3-butane diol
- 98-80-6
phenylboronic acid
- 24388-23-6
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
| Conditions | Yield |
|---|---|
| at 0℃; for 1h; | 100% |
| In pentane at 0 - 20℃; for 3h; | 100% |
| In tetrahydrofuran at 20℃; for 1h; | 95% |
- 108-90-7
chlorobenzene
- 73183-34-3
bis(pinacol)diborane
- 24388-23-6
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
| Conditions | Yield |
|---|---|
| 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% |
- 108-86-1
bromobenzene
- 73183-34-3
bis(pinacol)diborane
- 24388-23-6
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
| Conditions | Yield |
|---|---|
| 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% |
- 76-09-5
2,3-dimethyl-2,3-butane diol
- 24388-23-6
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
| Conditions | Yield |
|---|---|
| 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% |
- 73183-34-3
bis(pinacol)diborane
A
- 24388-23-6
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
| Conditions | Yield |
|---|---|
| In benzene-d6 at 150℃; for 4h; Sealed tube; Inert atmosphere; | A 97% B 93% |
- 591-50-4
iodobenzene
- 25015-63-8
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
- 24388-23-6
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
| Conditions | Yield |
|---|---|
| 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% |
- 369-57-3
benzenediazonium tetrafluoroborate
- 73183-34-3
bis(pinacol)diborane
- 24388-23-6
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
| Conditions | Yield |
|---|---|
| (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% |
(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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