2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Base Information

• Chemical Name: 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde
• CAS No.: 380151-85-9
• Molecular Formula: C13H17BO3
• Molecular Weight: 232.087
• Hs Code.: 29310099
• European Community (EC) Number: 625-516-9
• DSSTox Substance ID: DTXSID50450516
• Nikkaji Number: J1.686.432C
• Wikidata: Q72479385
• Mol file: 380151-85-9.mol

Synonyms:380151-85-9;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde;2-Formylphenylboronic acid pinacol ester;(2-FORMYLPHENYL)BORONIC ACID PINACOL ESTER;2-Formylphenylboronic acid, pinacol ester;2-Boronobenzaldehyde, pinacol ester;MFCD07363841;2-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-BENZALDEHYDE;2-(2-Formylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;SCHEMBL861866;2-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde;DTXSID50450516;SLJMPQLPRHIAOM-UHFFFAOYSA-N;BBL102134;STL555933;AKOS015960083;AS-2305;CS-W000921;SY050697;FT-0644536;T3161;2-Formylphenylboronic acid pinacol ester, 97%;EN300-184407;A823961;Z1880970987

Chemical Property of 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.514
• Boiling Point: 345.894 °C at 760 mmHg
• Flash Point: 162.991 °C
• PSA: 35.53000
• Density: 1.06g/cm³
• LogP: 1.79830
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 232.1270746
• Heavy Atom Count: 17
• Complexity: 285

Purity/Quality:

99% ^*data from raw suppliers

2-Formylphenylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2C=O
• Uses: 2-Formylphenylboronic acid pinacol ester can be used as a starting material to prepare:Profluorescent?probe applicable for the detection of H2O2?and Fe or Cu ions in living cells.Boronic acid pinacol ester derived nickel porphyrin, which is used to synthesize molecular spin switches and electron transfer dyads.Fluorescein hydrizido 2-imidophenylboronic ester, a fluorescent sensor prochelator applicable in the detection of copper ions.

Technology Process of 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

There total 30 articles about 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 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%

2,3-dimethyl-2,3-butane diol (76-09-5) + 2-formylbenzene boronic acid (40138-16-7) → 2-(2'-formylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (380151-85-9)

Guidance literature:

In benzene; for 5h; Heating;

DOI:10.1021/jo049874k

Reference yield: 98.0%

ortho-bromobenzaldehyde (6630-33-7) + bis(pinacol)diborane (73183-34-3) → 2-(2'-formylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (380151-85-9)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; for 36h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.6b00269

Reference yield: 92.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + potassium (2-formylphenyl)trifluoroborate → 2-(2'-formylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (380151-85-9)

Guidance literature:

With montmorillonite K₁₀; In tetrahydrofuran; at 25 ℃; Molecular sieve;

DOI:10.21577/0103-5053.20180126

upstream raw materials:

2,3-dimethyl-2,3-butane diol

2-formylbenzene boronic acid

E-Ethyl ester of 4-methyl-4,5-epoxy-2-pentenoic acid

ortho-bromobenzaldehyde

Downstream raw materials:

2-Phenylbenzaldehyde

4,4,5,5-tetramethyl-2-(2-vinylphenyl)-1,3,2-dioxaborolane

3H-benzo[c][1,2]oxaborol-1-ol

[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanol

Refernces

• 1、 Chen, Fener,Chen, Xiao-Pan,Deng, Ji,Li, Gen,Li, Guo-Bo,Schofield, Christopher J.,Xiao, You-Cai,Yan, Yu-Hang,Yu, Jun-Lin,Zhu, Kai-Rong,Brem, Jürgen. "Design and enantioselective synthesis of 3-(α-acrylic acid) benzoxaboroles to combat carbapenemase resistance". supporting information. p. 7709 - 7712. Retrieved 2021/08/09.
• 2、 Cai, Mingzhong,Huang, Bin,Luo, Chengkai,Xu, Caifeng. "Recyclable Pd2dba3/XPhos/PEG-2000 System for Efficient Borylation of Aryl Chlorides: Practical Access to Aryl Boronates". . . Retrieved 2021/12/02.