Allylboronic acid pinacol ester

Base Information

• Chemical Name: Allylboronic acid pinacol ester
• CAS No.: 72824-04-5
• Molecular Formula: C9H17BO2
• Molecular Weight: 168.044
• Hs Code.: 29310095
• European Community (EC) Number: 672-877-3
• DSSTox Substance ID: DTXSID70376784
• Nikkaji Number: J306.393C
• Wikidata: Q72437188
• Mol file: 72824-04-5.mol

Synonyms:Allylboronic acid pinacol ester;72824-04-5;2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;Allylboronic acid, pinacol cyclic ester;4,4,5,5-tetramethyl-2-prop-2-enyl-1,3,2-dioxaborolane;allyl boronic acid pinacol ester;ALLYLBORONIC ACID PIRACOL ESTER;4,4,5,5-tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolane;PINACOLYL 2-PROPENYLBORONATE;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(2-propenyl)-;MFCD00013347;Allylboronic acid pinacolate;SCHEMBL838241;allyl-boronic acid pinacol ester;DTXSID70376784;YMHIEPNFCBNQQU-UHFFFAOYSA-N;AKOS000265360;Allylboronic acid pinacol ester, 97%;AB01126;AM90123;CS-W000963;AS-11409;AS-81501;FT-0622041;EN300-105979;A837633;A936741;J-519557;2-allyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;2-allyl-4,4,5,5-tetramethyl-1,3,2-dioxa-borolane;Z1203162558;4,4,5,5-tetramethyl-2-prop-2-en-1-yl-1,3,2-dioxaborolane

Chemical Property of Allylboronic acid pinacol ester

Chemical Property:

• Appearance/Colour: Clear corless liquid
• Vapor Pressure: 11.294mmHg at 25°C
• Refractive Index: n20/D 1.4268(lit.)
• Boiling Point: 171 °C at 760 mmHg
• Flash Point: 57.2 °C
• PSA: 18.46000
• Density: 0.88 g/cm³
• LogP: 2.26460
• Storage Temp.: Refrigerator
• Water Solubility.: Not miscible or difficult to mix in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 168.1321599
• Heavy Atom Count: 12
• Complexity: 171

Purity/Quality:

99% ^*data from raw suppliers

Allylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)CC=C
• Uses: Allylboronic acid pinacol ester can act as reagent used for Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions and olefin metathesis; Intermolecular radical additions; Allylboration of aldehydes catalyzed by chiral spirobiindane diol (SPINOL) based phosphoric acids and Cobalt-catalyzed regioselective hydrovinylation of dienes with alkenes ; Nucleic acid-templated energy transfer leading to a photorelease reaction . Allylboronic acid pinacol ester reacts with carboxylic acids, in the presence of tri-n-butyltin hydride, to give homoallylic alcohols in good yield. Homoallylic alcohols can also be formed by allylboration of aldehydes. It is a reagent used for palladium-catalyzed Suzuki-Miyaura cross-coupling reactions and olefin metathesis, intermolecular radical additions, allylboration of aldehydes catalyzed by chiral spirobiindane diol (SPINOL) based phosphoric acids, cobalt-catalyzed regioselective hydrovinylation of dienes with alkenes, nucleic acid-templated energy transfer leading to a photorelease reaction and stereoselective indium-catalyzed Hosomi-Sakurai reactions.

Technology Process of Allylboronic acid pinacol ester

There total 19 articles about Allylboronic 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: 84.0%

(E)-propenyl lithium (6386-72-7,6524-17-0,29283-76-9) + 2-(1-bromo-1-methylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → pinacol 1-<1,1-dimethyl-2(E)-butenyl>boronate (96041-10-0) + 4,4,5,5-tetramethyl-2-(1-propenyl)-1,3,2-dioxaborolane (72824-04-5,83947-58-4,83947-59-5,72824-05-6)

Guidance literature:

In diethyl ether; (E)-propenyllithium (6.87 mmol) in Et2O soln. was added dropwise during45 min under Ar to a soln. of 2-bromo-2-propylboronate (6.21 mmol) in Et2O at -78°C;; distn. at 68-70°C (5 mm Hg)gve the product (98% isomerically pure);

DOI:10.1021/ja00272a043

Reference yield: 70.0%

C14H16O3 (339552-93-1) + bis(pinacol)diborane (73183-34-3) → ethyl 3-(4-hydroxyphenyl)prop-2-enoate (7361-92-4,7362-39-2,2979-06-8) + 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72824-04-5)

Guidance literature:

With sodium t-butanolate; ((2S,3S)-6-mesityl-2,3-diphenyl-2,3,5,6-tetrahydroimidazo[1,2-c]quinazolin-5-yl)copper(I)chloride; In methanol; diethyl ether; at -20 ℃; for 0.166667h; Product distribution / selectivity;

Reference yield: 67.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + allyl diethyl phosphate (3066-75-9) + bis(pinacol)diborane (73183-34-3) → C17H25BO2 + 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72824-04-5)

Guidance literature:

With [(1S,4R)-3-[4-(diphenylphosphino)-2,5-dimethyl-3-thienyl]-4,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl]diphenylphosphine; copper(l) chloride; sodium t-butanolate; In tetrahydrofuran; at 22 ℃; for 14h; enantioselective reaction; Inert atmosphere;

DOI:10.1038/NCHEM.2861

upstream raw materials:

C₁₄H₁₆O₃

bis(pinacol)diborane

Allyl acetate

1-tert-butyl-4-iodobenzene

Downstream raw materials:

allylbenzene

1-propenylbenzene

biphenyl

(1E)-1,3-diphenylpropene

Refernces

• 1、 Ivon, Yevhen M.,Kuchkovska, Yuliya O.,Voitenko, Zoya V.,Grygorenko, Oleksandr O.. "Aliphatic α-Boryl-α-bromoketones: Synthesis and Reactivity". . p. 3367 - 3377. Retrieved 2020/03/13.
• 2、 García-Domínguez, Andrés,Li, Zhaodong,Nevado, Cristina. "Nickel-Catalyzed Reductive Dicarbofunctionalization of Alkenes". supporting information. p. 6835 - 6838. Retrieved 2017/06/01.