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

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborolane
• CAS No.: 190788-59-1
• Molecular Formula: C12H16BNO4
• Molecular Weight: 249.074
• Hs Code.: 2934999090
• European Community (EC) Number: 681-615-7
• DSSTox Substance ID: DTXSID70395213
• Nikkaji Number: J845.357H
• Wikidata: Q72494289
• Mol file: 190788-59-1.mol

Synonyms:190788-59-1;4,4,5,5-tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborolane;2-Nitrobenzeneboronic acid pinacol ester;2-Nitrophenylboronic acid pinacol ester;(2-Nitrophenyl)boronic acid pinacol ester;2-NITROPHENYLBORONIC ACID, PINACOL ESTER;1,3,2-DIOXABOROLANE, 4,4,5,5-TETRAMETHYL-2-(2-NITROPHENYL)-;MFCD02179447;SCHEMBL7690779;DTXSID70395213;VLJYUDGCEKORNG-UHFFFAOYSA-N;2-(2-NITROPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;AKOS015951144;AB11147;AS-2981;CS-W000891;SY108998;(2-Nitrophenyl)boronic acid, pinacol ester;A4207;FT-0643801;N1006;EN300-267736;2-nitrobenzeneboronic acid pinacol ester, AldrichCPR;J-513974;Z2044805156;1-Nitro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene;3-hydroxy-2,3-dimethylbutan-2-yl hydrogen 2-nitrophenylboronate

Chemical Property of 4,4,5,5-Tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 5.36E-05mmHg at 25°C
• Melting Point: 42-44°C
• Refractive Index: 1.515
• Boiling Point: 358.2 °C at 760 mmHg
• Flash Point: 170.4 °C
• PSA: 86.28000
• Density: 1.14 g/cm³
• LogP: -0.20220
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 249.1172382
• Heavy Atom Count: 18
• Complexity: 324

Purity/Quality:

98% ^*data from raw suppliers

4,4,5,5-Tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborolane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: R36/37/38:Irritating to eyes, respiratory system and skin.
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2[N+](=O)[O-]

Technology Process of 4,4,5,5-Tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborolane

There total 11 articles about 4,4,5,5-Tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborolane 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: 97.0%

2-nitrophenyl bromide (577-19-5) + bis(pinacol)diborane (73183-34-3) → 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene (190788-59-1)

Guidance literature:

With potassium acetate; In 1,4-dioxane; at 80 ℃; for 12h; Inert atmosphere;

Reference yield: 90.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 2-nitrophenyl bromide (577-19-5) → 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene (190788-59-1)

Guidance literature:

2-nitrophenyl bromide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 25h;

Reference yield: 80.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + o-nitroiodobenzene (609-73-4) → 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene (190788-59-1)

Guidance literature:

o-nitroiodobenzene; With phenyllithium; In tetrahydrofuran; diethyl ether; cyclohexane; at -28 ℃; for 1.52778E-05h;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; diethyl ether; cyclohexane; at -28 ℃; for 0.000611111h;

DOI:10.1039/c2cc36197c

upstream raw materials:

Phenyl triflate

2-nitrophenyl trifluoromethanesulfonate

2-nitrophenyl bromide

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

Downstream raw materials:

ethyl 2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1-(2-chlorobenzyl)-4-(2-nitrophenyl)-1H-imidazole-5-carboxylate

3-morpholinonitrobenzene

2-anilineboronic acid pinacol ester

Refernces

• 1、 -. "Carbazole derivatives and organoelectro luminescent device using the same". Paragraph 0366; 0403-0408. . Retrieved 2020/11/28.
• 2、 -. "NITRATION". Page/Page column 36; 41; 46; 64; 38; 52; 42; 65. . Retrieved 2020/05/28.