Tert-butylboronic acid pinacol ester

Base Information

• Chemical Name: Tert-butylboronic acid pinacol ester
• CAS No.: 99810-76-1
• Molecular Formula: C10H21BO2
• Molecular Weight: 184.087
• Hs Code.: 2934999090
• European Community (EC) Number: 812-430-3
• DSSTox Substance ID: DTXSID70391230
• Nikkaji Number: J3.166.294J
• Wikidata: Q72502448
• Mol file: 99810-76-1.mol

Synonyms:99810-76-1;TERT-BUTYLBORONIC ACID PINACOL ESTER;2-(tert-Butyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-tert-butyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;MFCD06657801;1,3,2-Dioxaborolane, 2-(1,1-dimethylethyl)-4,4,5,5-tetramethyl-;SCHEMBL734240;DTXSID70391230;BCP12578;tert-butyl boronic acid pinacol ester;AKOS006344486;AB25678;CS-W018607;GS-6924;SY025584;FT-0703889;EN300-316304;A858419;Z1201623578

Chemical Property of Tert-butylboronic acid pinacol ester

Chemical Property:

• Vapor Pressure: 0.908mmHg at 25°C
• Refractive Index: 1.4105
• Boiling Point: 186.518 °C at 760 mmHg
• Flash Point: 66.604 °C
• PSA: 18.46000
• Density: 0.872 g/cm³
• LogP: 2.87870
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 184.1634601
• Heavy Atom Count: 13
• Complexity: 188

Purity/Quality:

98% ^*data from raw suppliers

tert-ButylboronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C(C)(C)C

Technology Process of Tert-butylboronic acid pinacol ester

There total 12 articles about Tert-butylboronic 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: 71.0%

t-butyl bromide (507-19-7) + 2-(4-iodobutoxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 2-(tert-butyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (99810-76-1)

Guidance literature:

With magnesium; In tetrahydrofuran; at 25 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tetlet.2014.12.033

Reference yield: 65.0%

→ 2-(tert-butyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (99810-76-1)

Guidance literature:

In tetrahydrofuran; at 25 ℃; for 1.08333h;

With hydrogenchloride; In tetrahydrofuran; water; at 0 - 25 ℃; for 0.666667h;

Reference yield: 63.0%

N-methyl-2-(1,1-dimethylethyl)indole (46275-90-5) + bis(pinacol)diborane (73183-34-3) → 1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (596819-10-2) + 2-(tert-butyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (99810-76-1)

Guidance literature:

N-methyl-2-(1,1-dimethylethyl)indole; bis(pinacol)diborane; With Trimethyl borate; triethylamine; In octane; at 160 ℃; for 48h;

With hydrogenchloride; In water; for 0.5h; regioselective reaction;

DOI:10.1039/d1sc04487g

upstream raw materials:

tert-butylmagnesium bromide

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

t-butyl bromide

1-bromomethyl-3-methoxybenzene

Downstream raw materials:

4-Phenylbut-1-ene

(E)-1-iodo-4-phenyl-1-butene

(Z)-(5,5-dimethylhex-3-en-1-yl)benzene

t-butylboronic acid

Refernces

• 1、 Procter, Richard J.,Dunsford, Jay J.,Rushworth, Philip J.,Hulcoop, David G.,Layfield, Richard A.,Ingleson, Michael J.. "A Zinc Catalyzed C(sp3)?C(sp2) Suzuki–Miyaura Cross-Coupling Reaction Mediated by Aryl-Zincates". supporting information. p. 15889 - 15893. Retrieved 2017/10/24.
• 2、 Dunsford, Jay J.,Clark, Ewan R.,Ingleson, Michael J.. "Highly nucleophilic dipropanolamine chelated boron reagents for aryl-transmetallation to iron complexes". supporting information. p. 20577 - 20583. Retrieved 2015/12/04.