2-(Cyclopent-1-EN-1-YL)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(Cyclopent-1-EN-1-YL)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 287944-10-9
• Molecular Formula: C11H19BO2
• Molecular Weight: 194.082
• Hs Code.: 2934999090
• European Community (EC) Number: 801-068-1
• ChEMBL ID: CHEMBL4472623
• DSSTox Substance ID: DTXSID50573234
• Nikkaji Number: J1.414.670I
• Pharos Ligand ID: A4HP127JQCRV
• Wikidata: Q72460395
• Mol file: 287944-10-9.mol

Synonyms:287944-10-9;2-(CYCLOPENT-1-EN-1-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;1-Cyclopentenylboronic acid pinacol ester;1-Cyclopenteneboronic Acid Pinacol Ester;2-(1-Cyclopenten-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;1,3,2-DIOXABOROLANE, 2-(1-CYCLOPENTEN-1-YL)-4,4,5,5-TETRAMETHYL-;Cyclopenten-1-ylboronic acid pinacol ester;2-(cyclopenten-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;Cyclopentene-1-boronic acid, pinacol ester;CHEMBL4472623;MFCD08669391;Cyclopenten-1-ylboronic acid, pinacol ester;2-(1-Cyclopentenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;SCHEMBL169762;DTXSID50573234;JFTZVYKESKQING-UHFFFAOYSA-N;2-(cyclopent-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-cyclopent-1-enyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;BDBM50510522;AKOS006290766;AM85294;CS-W004785;GS-5804;MB06422;AC-33896;SY021619;Cyclopenten-1-ylboronic acid,pinacol ester;C3385;EN300-98773;A21672;H10638;J-506342;Z1198180596;2-cyclopent-1-en-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 2-(Cyclopent-1-EN-1-YL)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0.284mmHg at 25°C
• Refractive Index: 1.463
• Boiling Point: 210 °C at 760 mmHg
• Flash Point: 80.8 °C
• PSA: 18.46000
• Density: 0.96 g/cm³
• LogP: 2.72810
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 194.1478100
• Heavy Atom Count: 14
• Complexity: 253

Purity/Quality:

98% ^*data from raw suppliers

1-Cyclopentenylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CCCC2

Technology Process of 2-(Cyclopent-1-EN-1-YL)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 14 articles about 2-(Cyclopent-1-EN-1-YL)-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: 99.0%

1-chlorocyclopent-1-ene (930-29-0) + bis(pinacol)diborane (73183-34-3) → 2-cyclopent-1-enyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (287944-10-9)

Guidance literature:

With potassium acetate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos; In 1,4-dioxane; at 110 ℃; for 3h; Inert atmosphere;

Reference yield: 95.0%

cyclopentene (142-29-0) + bis(pinacol)diborane (73183-34-3) → 2-cyclopent-1-enyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (287944-10-9)

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; at 70 ℃; for 16h; regioselective reaction; Inert atmosphere;

DOI:10.1021/jo9014694

Reference yield: 86.0%

bis(pinacol)diborane (73183-34-3) + cyclopent-1-en-1-yl(phenyl)iodonium tetrafluoroborate → 2-cyclopent-1-enyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (287944-10-9)

Guidance literature:

With copper(l) iodide; triphenylphosphine; lithium tert-butoxide; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h; Schlenk technique; Inert atmosphere;

DOI:10.1039/d0ob01121e

upstream raw materials:

1-iodocyclopentene

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

1-cyclopentenyl triflate

bis(pinacol)diborane

Downstream raw materials:

(4R,5R)-4,5-bis(2-cyclopentenylphenyl)-2,2-dimethyl-1,3-dioxolane

2-cyclopentyl-aniline

1-cyclopentyl-2-isothiocyanatobenzene

N-(2-cyclopentylphenyl)hydrazinecarbothioamide

Refernces

• 1、 Bao, Robert Li-Yuan,Gan, Shaoyan,Shi, Lei,Zhu, Dan. "Copper-catalyzed cross-coupling of vinyliodonium salts and diboron reagents to generate alkenyl boronic esters". supporting information. p. 5567 - 5570. Retrieved 2020/08/21.
• 2、 Bhakta, Urmibhusan,Sullivan, Erin,Hall, Dennis G.. "Catalytic enantioselective allylboration of propargylic aldehydes". supporting information. p. 678 - 683. Retrieved 2014/02/14.