| Identification | More | [Name]
2-Nitrophenylboronic acid | [CAS]
5570-19-4 | [Synonyms]
2-NITROBENZENEBORONIC ACID
2-NITROPHENYLBORONIC ACID
O-NITROPHENYLBORONIC ACID
RARECHEM AH PB 0142
2-Borononitrobenzene~2-Nitrophenylboronic acid
2-Borononitrobenzene
2-Nitrophenylboronic acid O2NC6H4B(OH)2
2-Nitrophenylboronic Acid (contains varying amounts of Anhydride) | [EINECS(EC#)]
611-304-3 | [Molecular Formula]
C6H6BNO4 | [MDL Number]
MFCD00161358 | [Molecular Weight]
166.93 | [MOL File]
5570-19-4.mol |
| Chemical Properties | Back Directory | [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 | [form ]
Crystalline Powder | [pka]
7.83±0.53(Predicted) | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
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 . | [WGK Germany ]
3 | [Hazard Note ]
Harmful | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [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 |
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