3-Nitrophenylboronic acid pinacol ester

Base Information

• Chemical Name: 3-Nitrophenylboronic acid pinacol ester
• CAS No.: 68716-48-3
• Molecular Formula: C12H16BNO4
• Molecular Weight: 249.074
• Hs Code.: 2934999090
• European Community (EC) Number: 624-690-3
• DSSTox Substance ID: DTXSID00460569
• Wikidata: Q72495301
• Mol file: 68716-48-3.mol

Synonyms:68716-48-3;3-Nitrophenylboronic acid pinacol ester;4,4,5,5-tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane;3-nitrophenylboronic acid, pinacol ester;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene;MFCD05663879;3-NITROBENZENEBORONIC ACID PINACOL ESTER;3 - Nitrobenzene boric acid pinacol ester;(3-NITROPHENYL)BORONIC ACID PINACOL ESTER;SCHEMBL103381;DTXSID00460569;JWEAFTZTLIGAQU-UHFFFAOYSA-N;1,3,2-DIOXABOROLANE, 4,4,5,5-TETRAMETHYL-2-(3-NITROPHENYL)-;AKOS015951145;AB22006;AM87141;AS-2751;CS-W010221;3-nitrophenyl boronic acid pinacol ester;SY059195;tetra-methylethylene 3-nitrobenzeneboronate;FT-0641203;3-Nitrophenylboronic acid pinacol ester, 97%;EN300-1706258;A836224;3-Nitrophenylboronic Acid Pinacol Ester

Chemical Property of 3-Nitrophenylboronic acid pinacol ester

Chemical Property:

• Vapor Pressure: 8.17E-05mmHg at 25°C
• Melting Point: 76-80 °C(lit.)
• Refractive Index: 1.515
• Boiling Point: 351.7 °C at 760 mmHg
• Flash Point: 166.5 °C
• PSA: 64.28000
• Density: 1.14 g/cm³
• LogP: 2.41720
• Storage Temp.: 2-8°C
• 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

3-Nitrophenylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC=C2)[N+](=O)[O-]
• Uses: 3-Nitrophenylboronic Acid Pinacol Ester is used in the preparation of [(pyrimidoindolyl)phenyl]benzamide derivatives and analogs as Janus kinase inhibitors.

Technology Process of 3-Nitrophenylboronic acid pinacol ester

There total 17 articles about 3-Nitrophenylboronic acid pinacol ester 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%

2,3-dimethyl-2,3-butane diol (76-09-5) + m-nitrobenzene boronic acid (13331-27-6) → 4,4,5,5-tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane (68716-48-3)

Guidance literature:

With sodium sulfate; In tetrahydrofuran; at 20 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1002/adsc.201300741

Reference yield: 97.0%

m-nitrobromobenzene (585-79-5) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane (68716-48-3)

Guidance literature:

With DPEPhos; sodium acetate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; for 12h; Heating;

DOI:10.1002/adsc.201500844

Reference yield: 96.0%

3-nitro-aniline (99-09-2) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane (68716-48-3)

Guidance literature:

3-nitro-aniline; With hydrogenchloride; methanol; sodium nitrite; In water; at 0 - 5 ℃; for 0.5h; Green chemistry;

bis(pinacol)diborane; In water; at 20 ℃; for 1h; Green chemistry;

DOI:10.1055/s-0033-1339118

upstream raw materials:

pinacolboronic acid

trifluoromethanesulfonic acid 3-nitrophenyl ester

m-nitrobromobenzene

bis(pinacol)diborane

Downstream raw materials:

m-nitrobromobenzene

meta-nitrophenol

6-methyl-3'-nitro-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide

6-chloro-3'-nitro-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide

Refernces

• 1、 -. "TYK2 INHIBITORS AND USES THEREOF". Paragraph 00339. . Retrieved 2020/06/19.
• 2、 -. "NITRATION". Page/Page column 36; 41; 46; 64; 38; 52; 42; 65. . Retrieved 2020/05/28.