2-Nitrophenylboronic acid

Base Information

• Chemical Name: 2-Nitrophenylboronic acid
• CAS No.: 5570-19-4
• Molecular Formula: C6H6BNO4
• Molecular Weight: 166.929
• Hs Code.: 29319090
• DSSTox Substance ID: DTXSID20901106
• Nikkaji Number: J1.113.654K
• Wikidata: Q72495297
• ChEMBL ID: CHEMBL313388
• Mol file: 5570-19-4.mol

Synonyms:2-Nitrophenylboronic acid;5570-19-4;(2-nitrophenyl)boronic Acid;2-Nitrobenzeneboronic Acid;Boronic acid, (nitrophenyl)-;MFCD00161358;2-nitrophenyl boronic acid;nitrophenylboronic acid;nitrobenzeneboronic acid;NoName_166;2-Nitrophenylboronicacid;2-nitrophenyl-boronic acid;(2-nitrophenyl)boronicAcid;2-Nitro-benzeneboronic acid;nitrooxy(phenyl)borinic acid;SCHEMBL28117;CHEMBL313388;SCHEMBL14727517;O-NITROBENZENEBORONIC ACID;DTXSID20901106;SFUIGUOONHIVLG-UHFFFAOYSA-N;Boronic acid, B-(2-nitrophenyl)-;Iodoanthranilicacidmethylester;98%;AKOS015833512;AB04234;AM62717;AS-2978;CS-W002465;OL10072;SY023827;FT-0613179;N0811;EN300-120491;A830763;J-510170;67132-35-8

Chemical Property of 2-Nitrophenylboronic acid

Chemical Property:

• Appearance/Colour: Off-white powder
• Melting Point: 155-160 °C
• Boiling Point: 374.78 °C at 760 mmHg
• PKA: 7.83±0.53(Predicted)
• Flash Point: 180.461 °C
• PSA: 86.28000
• Density: 1.4 g/cm³
• LogP: -0.20220
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol,Ether,Ethanol
• 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

2-Nitrophenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=CC=C1[N+](=O)[O-])(O)O
• Uses: Boronic acid catalyst used for: Mild and selective dipolar cycloadditions of unsaturated carboxylic acids with azidesTransposition of allylic alcohols and Meyer-Schuster rearrangementsReactant involved in: Suzuki-Miyaura cross-coupling reactions with aryl halides or nitroarenediazonium tetrafluoroboratesCopper-catalyzed halogenationOxidative arylation of aminopyrazolyl disulfides

Technology Process of 2-Nitrophenylboronic acid

There total 11 articles about 2-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: 99.0%

phenylboronic acid (98-80-6) → 2-nitrophenylboronic acid (5570-19-4)

Guidance literature:

With nitric acid; N,N-dimethyl-formamide; sodium nitrite; at 45 ℃; Reagent/catalyst; Solvent; Temperature;

Reference yield: 89.0%

Trimethyl borate (121-43-7,63156-11-6) + o-nitroiodobenzene (609-73-4) → 2-nitrophenylboronic acid (5570-19-4)

Guidance literature:

o-nitroiodobenzene; With phenylmagnesium chloride; In tetrahydrofuran; at -78 ℃;

Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃;

With hydrogenchloride; In tetrahydrofuran;

Reference yield: 85.0%

o-nitroiodobenzene (609-73-4) → 2-nitrophenylboronic acid (5570-19-4)

Guidance literature:

o-nitroiodobenzene; With phenylmagnesium chloride; In tetrahydrofuran; at -60 ℃; for 0.0833333h;

With Trimethyl borate; In tetrahydrofuran; at -60 ℃; for 0.5h;

With hydrogenchloride; In tetrahydrofuran; at -20 ℃;

DOI:10.1016/j.tetlet.2005.04.129

upstream raw materials:

acetic anhydride

phenylboronic acid

o-nitroiodobenzene

Trimethyl borate

Downstream raw materials:

1-nitro-2-(2-nitrophenyl)benzene

2-aminophenylboronic acid

tris(2-nitrophenyl)-1,3,5,2,4,6-trioxatriborinane

Methyl 5-(2-Nitrophenyl)nicotinate

Refernces

• 1、 -. "Metal complex and OLED (Organic Light Emitting Device) thereof". Paragraph 0086; 0087; 0088; 0089. . Retrieved 2018/10/19.
• 2、 -. "A compound with anti-tumor activity of the multitarget kinase inhibitor and its preparation method". Paragraph 0061-0062. . Retrieved 2017/04/14.