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

Base Information

• Chemical Name: 2-Cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 126689-01-8
• Molecular Formula: C9H17BO2
• Molecular Weight: 168.044
• Hs Code.: 29319090
• DSSTox Substance ID: DTXSID50374127
• Nikkaji Number: J396.329B
• Wikidata: Q72460752
• Mol file: 126689-01-8.mol

Synonyms:126689-01-8;2-Cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;Cyclopropylboronic acid pinacol ester;cyclopropylboronic acid, pinacol ester;MFCD05663847;cyclopropyl boronic acid pinacol ester;1,3,2-DIOXABOROLANE, 2-CYCLOPROPYL-4,4,5,5-TETRAMETHYL-;(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropane;2-cyclopropyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;SCHEMBL584593;DTXSID50374127;XGBMQBPLWXTEPM-UHFFFAOYSA-N;2-CYCLOPROPYL-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROL;Cyclopropylboronic acid,pinacol ester;BBL103777;STL557587;AKOS004119276;2-Cyclopropylboronic acid pinacol ester;2-cyclopropylboronic acid,pinacol ester;AB21938;CS-W007591;Cyclopropane-1-boronic acid pinacol ester;DS-14940;SY016142;Cyclopropylboronic acid pinacol ester, 96%;AM20080203;C2276;FT-0649843;EN300-1706413;Q-102832

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

Chemical Property:

• Vapor Pressure: 0.000776mmHg at 25°C
• Refractive Index: n20/D 1.433
• Boiling Point: 177.158 °C at 760 mmHg
• Flash Point: 60.943 °C
• PSA: 18.46000
• Density: 0.954 g/cm³
• LogP: 2.24260
• Storage Temp.: Refrigerator
• Sensitive.: Moisture Sensitive
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 168.1321599
• Heavy Atom Count: 12
• Complexity: 181

Purity/Quality:

99% ^*data from raw suppliers

Cyclopropylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10
• Safety Statements: 16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2CC2
• Uses: suzuki reaction Cyclopropylboronic acid pinacol ester can be used:As a cyclopropylating reagent in the study of thiophenol S-cyclopropylation, catalyzed by copper(II) acetate.In one of the key synthetic steps for the preparation of 5-lipoxygenase activating protein (FLAP) inhibitor.

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

There total 10 articles about 2-Cyclopropyl-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: 91.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + C11H21BN2 → cyclopropylboronic acid pinacol ester (126689-01-8)

Guidance literature:

In tetrahydrofuran; for 1h; Inert atmosphere; Reflux;

Reference yield: 84.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + cyclopropylboronic acid (411235-57-9) → cyclopropylboronic acid pinacol ester (126689-01-8)

Guidance literature:

With magnesium sulfate; In dichloromethane; ethyl acetate; at 20 ℃;

DOI:10.1021/jacs.9b07960

Reference yield: 82.0%

cyclopropyl bromide (4333-56-6,130561-87-4) + bis(pinacol)diborane (73183-34-3) → cyclopropylboronic acid pinacol ester (126689-01-8)

Guidance literature:

With lithium tert-butoxide; In N,N-dimethyl-formamide; at 30 ℃; for 3h; under 760.051 Torr; Irradiation;

DOI:10.1016/j.jcat.2021.01.019

upstream raw materials:

cyclopropyl bromide

bis(pinacol)diborane

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

potassium cyclopropyltrifluoroborate

Downstream raw materials:

ethyl 2-chloro-5-cyclopropylbenzoate

2-cyclopropyl-5-nitro-3-phenylpyridine

4-cyclopropyl-3-(3-methoxy-propoxy)-benzoic acid methyl ester

N-[(5-chloro-2-isopropylphenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide

Refernces

• 1、 Zhao, Jia-Hui,Zhou, Zhao-Zhao,Zhang, Yue,Su, Xuan,Chen, Xi-Meng,Liang, Yong-Min. "Visible-light-mediated borylation of aryl and alkyl halides with a palladium complex". supporting information. p. 4390 - 4394. Retrieved 2020/10/20.
• 2、 -. "One-pot synthesis process for producing boron compounds". Paragraph 0036-0038. . Retrieved 2018/10/19.