| Identification | More | [Name]
5-Indoleboronic acid pinacol ester | [CAS]
269410-24-4 | [Synonyms]
1H-INDOLE-5-BORONIC ACID, PINACOL ESTER
5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDOLE
5-INDOLEBORONIC ACID, PINACOL ESTER
INDOLE-5-BORONIC ACID PINACOL ESTER
5-Indolylboronic acid, pinacol ester
5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1H-INDOLE 97+%
5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL) INDOLE
5-Indolylboronic acid, pinacol cyclic ester
1H-Indole-5-boronic acid pinacol ester ,97% | [Molecular Formula]
C14H20BNO3 | [MDL Number]
MFCD03789263 | [Molecular Weight]
261.12 | [MOL File]
269410-24-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Pale yellow to brownish crystalline powder | [Melting point ]
120-125 °C (lit.) | [Boiling point ]
396.0±15.0 °C(Predicted) | [density ]
1.11±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Crystalline Powder | [pka]
17.01±0.30(Predicted) | [color ]
Pale yellow to brown | [Water Solubility ]
Insoluble | [Detection Methods]
HPLC,NMR | [CAS DataBase Reference]
269410-24-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [Chemical Properties]
Pale yellow to brownish crystalline powder | [Uses]
Indole-5-boronic acid, pinacol ester | [Synthesis]
In a 500-mL single-necked flask, 5-bromoindole (20.00 g, 0.1 mol), bis(pinacolato)diboron (51.80 g, 0.2 mol), potassium acetate (22.80 g, 0.2 mol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (1.50 g), and 350 mL of dioxane were added in sequence. The reaction mixture was refluxed for 8 hours under nitrogen protection. After completion of the reaction, it was cooled to room temperature and the dioxane solvent was removed by rotary evaporator. Subsequently, the reaction mixture was washed with 200 ml of distilled water and extracted (3 times) with dichloromethane. The organic phases were combined and recrystallized by methanol-dichloromethane mixed solvent to give 21.8 g of 5-indoleboronic acid pinacol ester in 90% yield. | [References]
[1] Patent: CN105601612, 2016, A. Location in patent: Paragraph 0051; 0052; 0053
[2] Journal of Organic Chemistry, 2004, vol. 69, # 20, p. 6812 - 6820
[3] Organic Letters, 2012, vol. 14, # 2, p. 600 - 603
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 17, p. 4150 - 4155
[5] Patent: KR101603387, 2016, B1. Location in patent: Paragraph 0084-0088; 0143-0146 |
| Well-known Reagent Company Product Information | Back Directory | [Acros Organics]
5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole(269410-24-4) | [Sigma Aldrich]
269410-24-4(sigmaaldrich) | [TCI AMERICA]
5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole,>98.0%(GC)(269410-24-4) |
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