| Identification | More | [Name]
2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENOL | [CAS]
269409-97-4 | [Synonyms]
St5405622
522554_Aldrich
2-HYDROXYPHENYLBORONIC ACID, PINACOL ESTER
2-HYDROXYBENZENEBORONIC ACID, PINACOL ESTER
2-Hydroxyphenylboronic acid pinacol ester 98%
2-(Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
2-HYDROXYPHENYLBORONIC ACID, PINACOL CYCLIC ESTER
2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENOL
Phenol, 2-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-
2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol,97%
2-(2-HYDROXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol,min.97%
2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENOL, MIN. 97%
(3-hydroxy-2,3-dimethylbutan-2-yl)oxy-(2-hydroxyphenyl)borinic acid
2-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Phenol
2-Hydroxyphenylboronic Acid Pinacol Ester
2-(2-Hydroxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
2-Hydroxyphenylboronic Acid Pinacol Ester
2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 2-(2-Hydroxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | [Molecular Formula]
C12H17BO3 | [MDL Number]
MFCD02093754 | [Molecular Weight]
220.07 | [MOL File]
269409-97-4.mol |
| Chemical Properties | Back Directory | [Appearance]
pale yellow to brown liquid | [Boiling point ]
282 °C(lit.) | [density ]
1.05 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.506(lit.)
| [Fp ]
230 °F
| [storage temp. ]
Refrigerator | [Water Solubility ]
Insoluble in water | [form ]
liquid | [pka]
10.17±0.35(Predicted) | [color ]
pale yellow | [CAS DataBase Reference]
269409-97-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
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 | [TSCA ]
No | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [Chemical Properties]
pale yellow to brown liquid | [Uses]
Reactant involved in:
- Synthesis of indolo-fused heterocyclic inhibitors of polymerase enzyme of hepatitis C
- Studies of pi-interactions, electronic structure and transient UV absorption of subphthalocyanine-borate-bridged ferrocene-fullerene conjugates
- Synthesis of subphthalocyanine and fused-ring nicotine derivatives
- Suzuki-Miyaura coupling-triflation sequence, reduction and salt formation for synthesis of hydroxylated oligoarene phosphines
| [Uses]
2-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)phenol can be widely used in Suzuki coupling chemistry.
| [Synthesis]
GENERAL PROCEDURE: To a solution of o-aminophenol (0.5 mmol, 1.0 eq.) in methanol (1.0 mL) was added hydrochloric acid (0.5 mL, 1.5 mmol, 3.0 eq.) followed by water (0.5 mL). The mixture was stirred for 2 minutes and then sodium nitrite solution (0.25 mL) was added. Sodium nitrite solution was prepared by dissolving 35 mg of sodium nitrite in water (0.25 mL). The mixture was stirred at 0-5°C for 30 minutes, followed by the addition of a methanol (1.0 mL) solution of pinacol ester of bisboronic acid (2,381 mg, 1.5 mmol, 3.0 equiv). The reaction mixture was stirred for 60 minutes. Upon completion of the reaction, it was diluted with water (10 mL) and then extracted with dichloromethane (50 mL, 3 times). The organic layers were combined, washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, concentrated and the crude product was purified by fast chromatography to give 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol. | [References]
[1] Synlett, 2014, vol. 25, # 11, p. 1577 - 1584
[2] Journal of Organic Chemistry, 2013, vol. 78, # 5, p. 1923 - 1933 |
| Spectrum Detail | Back Directory | [Spectrum Detail]
2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENOL(269409-97-4)1HNMR
2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENOL(269409-97-4)1HNMR
2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENOL(269409-97-4)IR
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| Well-known Reagent Company Product Information | Back Directory | [Acros Organics]
2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 97%(269409-97-4) | [Sigma Aldrich]
269409-97-4(sigmaaldrich) | [TCI AMERICA]
2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol,>97.0%(GC)(269409-97-4) |
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