| Identification | More | [Name]
4'-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ACETANILIDE | [CAS]
214360-60-8 | [Synonyms]
2-(4-ACETAMIDOPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
4'-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ACETANILIDE
4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ACETANILIDE
4-ACETAMIDOPHENYLBORONIC ACID, PINACOL CYCLIC ESTER
4-ACETAMIDOPHENYLBORONIC ACID, PINACOL ESTER
4-ACETYLAMINOPHENYLBORONIC ACID PINACOL CYCLIC ESTER
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)acetanilide,min.97%
4-acetylaminophenylboronic acid pinacol ester
4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ACETANILIDE, MIN. 97%
4-Acetamidophenylboronic acid, pinacol cyclic ester, 4μ-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)acetanilide | [Molecular Formula]
C14H20BNO3 | [MDL Number]
MFCD02093722 | [Molecular Weight]
261.12 | [MOL File]
214360-60-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Light yellow to light beige powder | [Melting point ]
160-164 °C(lit.) | [Boiling point ]
423.2±28.0 °C(Predicted) | [density ]
1.07±0.1 g/cm3(Predicted) | [storage temp. ]
Refrigerator (+4°C) | [Water Solubility ]
Insoluble in water | [form ]
Powder | [pka]
15.26±0.70(Predicted) | [color ]
white | [InChI]
1S/C14H20BNO3/c1-10(17)16-12-8-6-11(7-9-12)15-18-13(2,3)14(4,5)19-15/h6-9H,1-5H3,(H,16,17) | [InChIKey]
ANGKVUVZQVUVJO-UHFFFAOYSA-N | [SMILES]
CC(=O)Nc1ccc(cc1)B2OC(C)(C)C(C)(C)O2 | [CAS DataBase Reference]
214360-60-8(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
| [TSCA ]
No | [HS Code ]
29349990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow to light beige powder | [Synthesis]
The general procedure for the synthesis of 4-acetylaminophenylboronic acid pinacol ester from 4-aminoacetanilide and bis(boronic acid) pinacol ester is as follows:
Example 6: Synthesis of N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide
In a 25 mL tubular reactor, N-(4-aminophenyl)acetamide (1 mmol, 150 mg), pinacol ester of bis(boronic acid) (B2pin2, 1.2 mmol, 305 mg), benzoyl peroxide (0.02 mmol, 5 mg), and acetonitrile (3 mL) were added sequentially. Subsequently, tert-butyl nitrite (1.5 mmol, 154 mg) was added. The reaction was carried out at room temperature with stirring for 1 hour. After completion of the reaction, the reaction solution was concentrated and purified by column chromatography (eluent: petroleum ether/ethyl acetate=20:1, V/V) to afford the target compound N-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide as a white solid in 93% yield.
The nuclear magnetic resonance (NMR) data of the compound are as follows:
1H NMR (400 MHz, CDCl3) δ 7.76 (d, 1H, J = 8.4 Hz), 7.53 (d, 1H, J = 8.3 Hz), 2.16 (s, 3H), 1.33-1.24 (m, 12H).
13C NMR (100 MHz, CDCl3) δ 168.5, 140.5, 135.6, 128.8, 119.9, 118.5, 83.6, 74.9, 24.9, 24.7, 24.5, 24.4. | [References]
[1] Angewandte Chemie - International Edition, 2010, vol. 49, # 10, p. 1846 - 1849
[2] Angewandte Chemie - International Edition, 2010, vol. 49, # 10, p. 1846 - 1849
[3] Patent: US2012/184768, 2012, A1. Location in patent: Page/Page column 3
[4] Patent: EP2481742, 2012, A1. Location in patent: Page/Page column 5 |
| Spectrum Detail | Back Directory | [Spectrum Detail]
4'-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ACETANILIDE(214360-60-8)1HNMR
4'-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ACETANILIDE(214360-60-8)IR
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