3-Nitrophenylboronic acid

Base Information

• Chemical Name: 3-Nitrophenylboronic acid
• CAS No.: 13331-27-6
• Molecular Formula: C6H6BNO4
• Molecular Weight: 166.929
• Hs Code.: 29310095
• European Community (EC) Number: 603-734-5
• NSC Number: 401539,59739
• UNII: JLC765W4PN
• DSSTox Substance ID: DTXSID2065416
• Nikkaji Number: J54.865K
• Wikidata: Q27093741
• Metabolomics Workbench ID: 147352
• ChEMBL ID: CHEMBL20945
• Mol file: 13331-27-6.mol

Synonyms:3-nitrobenzeneboronic acid;3-nitrophenylboronic acid;m-nitrobenzeneboronic acid;meta-nitrobenzeneboronic acid

Chemical Property of 3-Nitrophenylboronic acid

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 6.5E-06mmHg at 25°C
• Melting Point: 289-291 °C
• Refractive Index: 1.573
• Boiling Point: 363.3 °C at 760 mmHg
• PKA: 6.93±0.10(Predicted)
• Flash Point: 173.5 °C
• PSA: 86.28000
• Density: 1.4 g/cm³
• LogP: -0.20220
• Storage Temp.: 0-6°C
• Sensitive.: Hygroscopic
• Solubility.: soluble in Ethanol,Methanol,Ether
• Water Solubility.: soluble in hot water
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 167.0389878
• Heavy Atom Count: 12
• Complexity: 169

Purity/Quality:

99% ^*data from raw suppliers

3-Nitrobenzeneboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B(C1=CC(=CC=C1)[N+](=O)[O-])(O)O
• Uses: Catalyzes ene carbocyclization of acetylenic dicarbonyl compounds8 suzuki reaction 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.

Technology Process of 3-Nitrophenylboronic acid

There total 15 articles about 3-Nitrophenylboronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

4,4,5,5-tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane (68716-48-3) → m-nitrobenzene boronic acid (13331-27-6)

Guidance literature:

With hydrogenchloride; polystyrene boronic acid; In acetonitrile; at 20 ℃; for 18h;

DOI:10.1016/j.tetlet.2004.07.014

Reference yield: 86.0%

potassium 3-nitrophenyltrifluoroborate → m-nitrobenzene boronic acid (13331-27-6)

Guidance literature:

With water; silica gel; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jo901441u

Reference yield: 65.0%

5-(4-methoxyphenyl)-4,4-dimethyl-2-(3-nitrophenyl)[1,3,2]dioxaborolane → m-nitrobenzene boronic acid (13331-27-6)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 50 ℃; for 24h;

DOI:10.1016/j.tetlet.2005.10.010

upstream raw materials:

phenylboronic acid

m-nitrobromobenzene

4,4,5,5-tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane

water

Downstream raw materials:

1-methyl-2-(3-nitro-phenyl)-2,3-dihydro-1H-benzo[1,3,2]diazaborole

methyl O⁴,O⁶-(3-nitro-phenylboranediyl)-α-D-glucopyranoside

3-(3-nitrophenyl)-5-pyridinecarboxylic acid methyl ester

2‐(3‐nitrophenyl)naphthalene

Refernces

• 1、 Yan, Jun,Jin, Shan,Wang, Binghe. "A novel redox-sensitive protecting group for boronic acids, MPMP-diol". . p. 8503 - 8505. Retrieved 2005.
• 2、 Erb, William,Hellal, Akila,Albini, Mathieu,Rouden, Jacques,Blanchet, Jerome. "An easy route to (hetero)arylboronic acids". supporting information. p. 6608 - 6612. Retrieved 2014/06/09.