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

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane
• CAS No.: 171364-83-3
• Molecular Formula: C12H16BNO4
• Molecular Weight: 249.074
• Hs Code.: 29333990
• European Community (EC) Number: 664-253-4
• DSSTox Substance ID: DTXSID60378550
• Nikkaji Number: J845.350K
• Wikidata: Q72495303
• ChEMBL ID: CHEMBL2024454
• Mol file: 171364-83-3.mol

Synonyms:171364-83-3;4,4,5,5-tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane;4-Nitrophenylboronic acid pinacol ester;4-Nitrophenylboronic acid, pinacol ester;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(4-nitrophenyl)-;MFCD02179437;(4-NITROPHENYL)BORONIC ACID, PINACOL ESTER;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene;SCHEMBL56104;CHEMBL2024454;DTXSID60378550;BCP15090;CS-M0976;RB3074;AKOS015920324;GS-6751;PB41224;4-Nitrobenzeneboronic acid pinacol ester;AC-22594;SY033603;AM20030145;FT-0643643;T3710;EN300-211493;A811325;J-010717;J-513978;J-515885;Z2037318348;2-(4-Nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborole;4,4,5,5-tetramethyl-2-(4-nitrophenyl)-[1,3,2]dioxaborolane;4,4,5,5-tetramethyl-2-(4-nitro-phenyl)-[1,3,2]dioxaborolane

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

Chemical Property:

• Vapor Pressure: 5.58E-05mmHg at 25°C
• Melting Point: 112-116 °C(lit.)
• Refractive Index: 1.515
• Boiling Point: 357.544 °C at 760 mmHg
• Flash Point: 170.037 °C
• PSA: 64.28000
• Density: 1.148 g/cm³
• LogP: 2.41720
• Storage Temp.: Store Cold
• Water Solubility.: Slightly soluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 249.1172382
• Heavy Atom Count: 18
• Complexity: 316

Purity/Quality:

98% ^*data from raw suppliers

4,4,5,5-Tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• 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=C(C=C2)[N+](=O)[O-]
• Uses: Reactant involved in: ? ;Synthesis of aryl azides 1? ;Arylation of allylic chlorides2? ;Syntehsis of RNA conjugates3? ;Alkoxycarbonylation4? ;Synthesis of mTOR and PI3K inhibitors as antitumor agents5? ;Electrooxidative synthesis of biaryls6 suzuki reaction 4-Nitrobenzeneboronic acid pinacol ester is a reactant involved in synthesis of aryl azides, arylation of allylic chlorides, synthesis of RNA conjugates, alkoxycarbonylation, synthesis of mTOR and PI3K inhibitors as antitumor agents, electro oxidative synthesis of biaryls.

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

There total 30 articles about 4,4,5,5-Tetramethyl-2-(4-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: 99.0%

4-chlorobenzonitrile (100-00-5) + bis(pinacol)diborane (73183-34-3) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene (171364-83-3)

Guidance literature:

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

DOI:10.1002/adsc.201500844

Reference yield: 99.0%

para-nitrophenyl bromide (586-78-7) + bis(pinacol)diborane (73183-34-3) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene (171364-83-3)

Guidance literature:

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

DOI:10.1002/adsc.201500844

Reference yield: 97.0%

4-nitro-aniline (100-01-6,104810-17-5) + bis(pinacol)diborane (73183-34-3) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene (171364-83-3)

Guidance literature:

4-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:

para-nitrophenyl triflate

Phenyl triflate

p-nitrobenzene iodide

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

Downstream raw materials:

N-(4-nitrophenyl)naphthalimide

4'-(2''-deoxy-β-D-ribofuranosyl)-4-nitrobiphenyl

2,2-dimethyl-7-(4-nitro-benzyl)-benzo[1,3]dioxin-4-one

C₁₇H₂₃NO₄Si

Refernces

• 1、 Hernández, José G.. "Mechanochemical borylation of aryldiazonium salts; merging light and ball milling". . p. 1463 - 1469. Retrieved 2017.
• 2、 Abe, Manabu,Chitose, Youhei,Lin, Tzu-Chau,Pham, Thuy Thi Thu,Tam, Tran Thi Thanh,Tseng, Wei-Lun. "Impact of Five-membered Heterocyclic Rings on Photophysical Properties including Two-photon Absorption Character". supporting information. p. 1810 - 1813. Retrieved 2021/10/27.
• 3、 Demonti, Luca,Mézailles, Nicolas,Nebra, Noel,Saffon-Merceron, Nathalie. "Cross-Coupling through Ag(I)/Ag(III) Redox Manifold". supporting information. p. 15396 - 15405. Retrieved 2021/10/12.