| Company Name: |
Energy Chemical |
| Tel: |
400-0056266 |
| Email: |
sales8178@energy-chemical.com |
|
| | 4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)acetanilide Basic information |
| Product Name: | 4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)acetanilide | | Synonyms: | 2-(4-ACETAMIDOPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;4-ACETYLAMINOPHENYLBORONIC ACID PINACOL CYCLIC ESTER;4-ACETAMIDOPHENYLBORONIC ACID, PINACOL CYCLIC ESTER;4-ACETAMIDOPHENYLBORONIC ACID, PINACOL ESTER;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,min.97%;4-acetylaminophenylboronic acid pinacol ester;4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ACETANILIDE, MIN. 97% | | CAS: | 214360-60-8 | | MF: | C14H20BNO3 | | MW: | 261.12 | | EINECS: | | | Product Categories: | organic or inorganic borate;Boronic acids;B (Classes of Boron Compounds);Boronic Acids Esters | | Mol File: | 214360-60-8.mol |  |
| | 4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)acetanilide Chemical Properties |
| Melting point | 160-164 °C(lit.) | | Boiling point | 423.2±28.0 °C(Predicted) | | density | 1.07±0.1 g/cm3(Predicted) | | storage temp. | Sealed in dry,2-8°C | | Water Solubility | Insoluble in water | | pka | 15.26±0.70(Predicted) | | form | Powder | | 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) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | TSCA | No | | HS Code | 29349990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)acetanilide Usage And Synthesis |
| 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] Patent: US2012/184768, 2012, A1. Location in patent: Page/Page column 3
[3] Patent: EP2481742, 2012, A1. Location in patent: Page/Page column 5 |
| | 4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)acetanilide Preparation Products And Raw materials |
|