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| | 3-Nitrophenylboronic acid Basic information | | Synthesis |
| | 3-Nitrophenylboronic acid Chemical Properties |
| Melting point | 284-285 °C (dec.) (lit.) | | Boiling point | 363.3±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 Ethanol,Methanol,Ether | | form | Powder | | pka | 6.93±0.10(Predicted) | | color | Light yellow to pale brown | | Water Solubility | soluble in hot water | | Sensitive | Hygroscopic | | BRN | 2938638 | | InChI | InChI=1S/C6H6BNO4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4,9-10H | | InChIKey | ZNRGSYUVFVNSAW-UHFFFAOYSA-N | | SMILES | B(C1=CC=CC([N+]([O-])=O)=C1)(O)O | | CAS DataBase Reference | 13331-27-6(CAS DataBase Reference) | | EPA Substance Registry System | Boronic acid, (3-nitrophenyl)- (13331-27-6) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-37/39-36 | | WGK Germany | 3 | | RTECS | CY8980000 | | Hazard Note | Harmful | | TSCA | TSCA listed | | HazardClass | IRRITANT | | HS Code | 29310095 | | Storage Class | 11 - Combustible Solids |
| | 3-Nitrophenylboronic acid Usage And Synthesis |
| Synthesis | 
Under ice-salt freezing conditions, a small amount of urea was added to colorless fuming nitric acid (50 mL, 1.20 M), and the mixture was cooled to -15 °C. Phenylated boric acid (9.02 g, 74 mmol) was slowly added over 1–2 hours to prevent the temperature from rising above -9 °C. The mixture was then stirred for another 15–30 minutes and poured onto ice, whereupon the product precipitated. The precipitated nitrophenylboronic acid was filtered under vacuum, recrystallized in a small amount of water, and decolorized charcoal was added. Hot vacuum filtration was then performed to remove the charcoal, followed by washing with water and then methanol. The original filtrate was cooled in an ice bath, neutralized with 12N NaOH to an orange/red solution, and then acidified with nitric acid. This solution was extracted with diethyl ether, washed with water, and concentrated at room temperature. The two fractions from the post-processing were combined and separated by column chromatography (eluent C6H12:CH2Cl2; 80:20) to remove all trace impurities, yielding prismatic lemon crystals in 28% yield. 3-Nitrophenylboronic acid, 28% yield. | | Chemical Properties | White to light yellow crystal powde | | Uses | Catalyzes ene carbocyclization of acetylenic dicarbonyl compounds8 | | Uses | suzuki reaction | | Uses | 3-Nitrophenylboronic Acid is a general reagent the preparation of carbon coated copper nanoparticles and nanowires for usage in Suzuki cross coupling reactions. Also it has been used in the synthesis of oxygenated cabazoles. | | Synthesis Reference(s) | The Journal of Organic Chemistry, 49, p. 5237, 1984 DOI: 10.1021/jo00200a045 |
| | 3-Nitrophenylboronic acid Preparation Products And Raw materials |
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