4-Nitrophenylboronic acid

Base Information

• Chemical Name: 4-Nitrophenylboronic acid
• CAS No.: 24067-17-2
• Molecular Formula: C6H6BNO4
• Molecular Weight: 166.929
• Hs Code.: 29319090
• European Community (EC) Number: 627-647-7
• DSSTox Substance ID: DTXSID50378549
• Nikkaji Number: J639.570H
• Wikidata: Q72495293
• ChEMBL ID: CHEMBL91108
• Mol file: 24067-17-2.mol

Synonyms:4-Nitrophenylboronic acid;24067-17-2;(4-nitrophenyl)boronic Acid;4-Nitrobenzeneboronic acid;p-nitrophenylboronic acid;4-Nitrophenyl boronic acid;Boronic acid, (4-nitrophenyl)-;MFCD00161360;p-nitrophenyl boronic acid;4-Nitro phenyl boronic acid;4-nitrobenzenboronic acid;(4-nitrophenyl)boranediol;4-nitro-phenylboronic acid;(4-nitrophenyl)boronicAcid;D0I3XN;para-nitrophenylboronic acid;SCHEMBL5993;4-nitro-phenyl boronic acid;CHEMBL91108;SCHEMBL14727519;BDBM26130;DTXSID50378549;NSFJAFZHYOAMHL-UHFFFAOYSA-N;CS-D0729;BBL103704;RB3032;STL557514;AKOS009157614;4-Nitrophenylboronic acid, >=95.0%;AB04238;GS-6522;NCGC00249507-01;AC-25841;PD131129;SY009037;AM20030424;FT-0638383;N0812;EN300-55471;A22280;J-015338;J-515884;Z838078136;UKH

Chemical Property of 4-Nitrophenylboronic acid

Chemical Property:

• Appearance/Colour: pale white powder
• Vapor Pressure: 3.02E-06mmHg at 25°C
• Melting Point: 285-290 °C (dec.)
• Refractive Index: 1.573
• Boiling Point: 373.7 °C at 760 mmHg
• PKA: 7.04±0.10(Predicted)
• Flash Point: 179.8 °C
• PSA: 86.28000
• Density: 1.4 g/cm³
• LogP: -0.20220
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility.: Slightly soluble in water.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 167.0389878
• Heavy Atom Count: 12
• Complexity: 161

Purity/Quality:

98% ^*data from raw suppliers

4-Nitrophenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 26-36/37/39-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)[N+](=O)[O-])(O)O
• Description: 4-Nitrobenzeneboronic acid is an arylboronic acid building block that has been used in the synthesis of phenols.
• Uses: 4-Nitrophenylboronic Acid is a useful synthetic intermediate. It is a reagent used for ligand-free palladium-catalyzed Suzuki-Miyaura cross-couplings, Ruthenium catalyzed direct arylation of benzylic sp3 carbons of acyclic amines and Diels-Alder or C-H activation reactions. Reagent used forLigand-free palladium-catalyzed Suzuki-Miyaura cross-couplings Ruthenium catalyzed direct arylation of benzylic sp3 carbons of acyclic amines Diels-Alder or C-H activation reactions Regioselective Suzuki-Miyaura coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulationsN-arylation of phenylurea using copper acetylacetonate catalyst Environmentally benign one-pot synthesis through a double arylation process Copper-mediated cyanations copper-catalyzed arylations Regioselective glycosylations Suzuki couplings followed by arylations X-ray absorption on rhodium-grafted hydrotalcite catalyst for heterogeneous 1,4-addition reaction of organoboron reagents to electron deficient olefins Reagent used in Preparation ofCombretastatin analogs as potential antitumor agents Human immunodeficiency virus (HIV) protease inhibitors with antiviral activities against drug-resistant viruses suzuki reaction

Technology Process of 4-Nitrophenylboronic acid

There total 16 articles about 4-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: 98.0%

tetrahydroxydiboron (13675-18-8) + 4-nitrobenzenediazonium trifluoromethanesulfonate → 4-nitrophenylboronic acid (24067-17-2)

Guidance literature:

In water; at 20 ℃; for 3.5h;

DOI:10.1002/ejoc.201800887

Reference yield: 78.0%

methanol (67-56-1) + diisopropylamine borane (55124-35-1) + para-nitrophenyl bromide (586-78-7) → 4-nitrophenylboronic acid (24067-17-2)

Guidance literature:

diisopropylamine borane; With magnesium; phenylmagnesium bromide; In tetrahydrofuran; at 20 ℃; for 0.166667h;

para-nitrophenyl bromide; In tetrahydrofuran; at 70 ℃;

methanol; Further stages;

DOI:10.1016/j.tet.2018.11.036

Reference yield: 76.0%

tetrahydroxydiboron (13675-18-8) + 4-nitro-aniline (100-01-6,104810-17-5) → 4-nitrophenylboronic acid (24067-17-2)

Guidance literature:

4-nitro-aniline; With hydrogenchloride; sodium nitrite; In water; at 0 ℃; for 0.25h;

tetrahydroxydiboron; With sodium acetate; In water; at 20 ℃; for 0.333333h;

DOI:10.1002/chem.201402487

upstream raw materials:

acetic anhydride

phenylboronic acid

p-nitrobenzene iodide

C₆H₄BF₃NO₂^(1-)

Downstream raw materials:

(4-aminophenyl)boronic acid

5-(4-nitrophenyl)-2-furaldehyde

Refernces

• 1、 Xia, Dong,Duan, Xin-Fang. "Alkylative Dearomatization by Using an Unactivated Aryl Nitro Group as a Leaving Group: Access to Diversified Alkylated Spiro[5.5]trienones". supporting information. p. 2548 - 2552. Retrieved 2021/05/05.
• 2、 Marciasini, Ludovic D.,Richard, Jimmy,Cacciuttolo, Bastien,Sartori, Guillaume,Birepinte, Melodie,Chabaud, Laurent,Pinet, Sandra,Pucheault, Mathieu. "Magnesium promoted autocatalytic dehydrogenation of amine borane complexes: A reliable, non-cryogenic, scalable access to boronic acids". . p. 164 - 171. Retrieved 2018/12/05.