2-Benzyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-Benzyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 87100-28-5
• Molecular Formula: C13H19BO2
• Molecular Weight: 218.104
• Hs Code.: 2934999090
• European Community (EC) Number: 679-569-8
• DSSTox Substance ID: DTXSID801007338
• Nikkaji Number: J1.147.021A
• Wikidata: Q72440840
• Mol file: 87100-28-5.mol

Synonyms:87100-28-5;Benzylboronic acid pinacol ester;2-benzyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;MFCD05663841;121074-61-1;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(phenylmethyl)-;benzylboronic pinacol ester;SCHEMBL142096;benzyl boronic acid pinacol ester;YCNQPAVKQPLZRS-UHFFFAOYSA-N;DTXSID801007338;benzylboronic acid pinacol ester 96%;AKOS005259533;AB21925;Benzylboronic acid pinacol ester, 96%;CS-W000993;DS-14900;SY013341;B3448;FT-0699342;EN300-222892;A935021;J-508110;Z1741972128;4,4,5,5-Tetramethyl-2-(phenylmethyl)-1,3,2-dioxaborolane

Chemical Property of 2-Benzyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0.0119mmHg at 25°C
• Refractive Index: n20/D 1.490
• Boiling Point: 269.6 °C at 760 mmHg
• Flash Point: 116.9 °C
• PSA: 49.69000
• Density: 0.98 g/cm³
• LogP: 2.08130
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Water Solubility.: Insoluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 218.1478100
• Heavy Atom Count: 16
• Complexity: 228

Purity/Quality:

98% ^*data from raw suppliers

Benzylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)CC2=CC=CC=C2
• Uses: Benzylboronic acid pinacol ester finds application in Pd (0)-mediated [11 C] carbonylation reaction.

Technology Process of 2-Benzyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 60 articles about 2-Benzyl-4,4,5,5-tetramethyl-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: 95.0%

benzyl bromide (100-39-0) + bis(pinacol)diborane (73183-34-3) → pinacol benzylboronate (87100-28-5)

Guidance literature:

With iron(III)-acetylacetonate; N,N,N,N,-tetramethylethylenediamine; ethylmagnesium bromide; In tetrahydrofuran; diethyl ether; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ja505199u

Reference yield: 93.0%

benzyl chloride (100-44-7) + bis(pinacol)diborane (73183-34-3) → pinacol benzylboronate (87100-28-5)

Guidance literature:

With iron(III)-acetylacetonate; magnesium; In tetrahydrofuran; at 0 ℃; for 3h; Inert atmosphere;

Reference yield: 92.0%

(phenylmethylene)bis(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolane) → pinacol benzylboronate (87100-28-5)

Guidance literature:

With silica gel; triethylamine; In ethyl acetate; pentane;

DOI:10.1002/anie.202110821

upstream raw materials:

tributylphenylstannane

pinacol (bromomethyl)boronate

toluene

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

Downstream raw materials:

2-[1-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-2-phenyl-ethyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

(S)-3-(4-benzyl-phenyl)-4-(3-trifluoromethyl-phenyl)-4-oxazolidin-2-one

(E)-1,4-diphenylbut-1-ene

N-tert-butoxycarbonylbenzylamine

Refernces

• 1、 Hu, Jiefeng,Huang, Mingming,Marder, Todd B.,Radius, Udo,Tang, Man,Westcott, Stephen A.. "Cu-mediated: vs. Cu-free selective borylation of aryl alkyl sulfones". supporting information. p. 395 - 398. Retrieved 2022/01/19.
• 2、 Cid, M. B.,Díaz, Cristina,Franco, Mario,Lamsabhi, Al Mokhtar,Sainz, Raquel,Tortosa, Mariola. "Evaluation of the role of graphene-based Cu(i) catalysts in borylation reactions". . p. 3501 - 3513. Retrieved 2021/06/06.