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| | 2-Nitrophenylboronic acid Basic information |
| | 2-Nitrophenylboronic acid Chemical Properties |
| Melting point | 155-160°C | | Boiling point | 374.8±44.0 °C(Predicted) | | density | 1.40±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | soluble in Methanol,Ether,Ethanol | | pka | 7.83±0.53(Predicted) | | form | Crystalline Powder | | color | White to off-white | | BRN | 3032097 | | InChI | InChI=1S/C6H6BNO4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4,9-10H | | InChIKey | SFUIGUOONHIVLG-UHFFFAOYSA-N | | SMILES | B(C1=CC=CC=C1[N+]([O-])=O)(O)O | | CAS DataBase Reference | 5570-19-4(CAS DataBase Reference) |
| Hazard Codes | Xn | | Risk Statements | 22-36/37/38 | | Safety Statements | 26 | | WGK Germany | 3 | | Hazard Note | Harmful | | HS Code | 29319090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Provider | Language |
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ALFA
| English |
| | 2-Nitrophenylboronic acid Usage And Synthesis |
| Chemical Properties | White to orange to brown solid | | Uses | Boronic acid catalyst used for:
- Mild and selective dipolar cycloadditions of unsaturated carboxylic acids with azides
- Transposition of allylic alcohols and Meyer-Schuster rearrangements
Reactant involved in:
- Suzuki-Miyaura cross-coupling reactions with aryl halides or nitroarenediazonium tetrafluoroborates
- Copper-catalyzed halogenation
- Oxidative arylation of aminopyrazolyl disulfides
| | Synthesis | Using phenylboronic acid as starting material, nitric acid (126 g, 2 mol) and sodium nitrite (0.04 mol) were added dropwise to the reaction system and the reaction temperature was controlled at 45 °C. The reaction mixture was reacted with dimethylformamide (15 mol) under stirring conditions. Upon completion of the reaction, the mixture was poured completely into ice water, concentrated to a small volume, cooled and allowed to stand until a solid precipitate precipitated. The solid was separated by filtration and washed with ice water, and the final product 2-nitrophenylboronic acid 165.3 g was collected in 99.0% molar yield and >99.5% HPLC purity. | | References | [1] Patent: CN104788484, 2017, B. Location in patent: Paragraph 0026-0039
[2] Patent: CN103214489, 2016, B. Location in patent: Paragraph 0061-0062
[3] Patent: US2005/192310, 2005, A1. Location in patent: Page/Page column 46
[4] Synlett, 2002, # 3, p. 477 - 479
[5] Journal of Organometallic Chemistry, 2003, vol. 680, # 1-2, p. 263 - 270 |
| | 2-Nitrophenylboronic acid Preparation Products And Raw materials |
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