Cyclopropylboronic acid

Base Information

• Chemical Name: Cyclopropylboronic acid
• CAS No.: 411235-57-9
• Molecular Formula: C3H7BO2
• Molecular Weight: 85.8984
• Hs Code.: 29319090
• DSSTox Substance ID: DTXSID00375402
• Nikkaji Number: J1.792.918F
• Wikidata: Q72460747
• Mol file: 411235-57-9.mol

Synonyms:Cyclopropylboronic acid;411235-57-9;Cyclopropyl Boronic Acid;CYCLOPROPANEBORONIC ACID;Cyclopropylboronicacid;MFCD04038750;BORONIC ACID, CYCLOPROPYL-;Boronic Acid, Cyclopropyl- (9Ci);cyclopropyl-boronic acid;cyclopropylboranediol;cyclopropyboronic acid;cyclopropylboromc acid;cycloproylboronic acid;cyclopropanboronic acid;cylcopropylboronic acid;cyclopropyl boronic cid;cycloproyl boronic acid;cyclo-propylboronic acid;cyclopropanylboronic acid;cyclopropane boronic acid;cyclo-propyl boronic acid;DTXSID00375402;WLVKDFJTYKELLQ-UHFFFAOYSA-N;BCP27024;CS-D1018;BBL104367;STL558619;ZB0043;AKOS004119250;AB17174;AC-6414;GS-6568;NCGC00249445-01;BP-10013;SY004028;A6833;AM20100093;FT-0630055;FT-0652978;EN300-30595;Q-200912

Chemical Property of Cyclopropylboronic acid

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0.0606mmHg at 25°C
• Melting Point: 90-95 °C(lit.)
• Refractive Index: 1.442
• Boiling Point: 205.1 °C at 760 mmHg
• PKA: 10.49±0.20(Predicted)
• Flash Point: 77.9 °C
• PSA: 40.46000
• Density: 1.11 g/cm³
• LogP: -0.37680
• Storage Temp.: Store below -20
• Sensitive.: moisture sensitive
• Solubility.: DMSO
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 86.0539096
• Heavy Atom Count: 6
• Complexity: 50.8

Purity/Quality:

99% ^*data from raw suppliers

Cyclopropylboronic acid 97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T
• Statements: 22-36-61-60-36/37/38
• Safety Statements: 26-36-45-53-37/39

MSDS Files:

Useful:

• Canonical SMILES: B(C1CC1)(O)O
• Uses: Cyclopropylboronic Acid is an organoboronic acid commonly used in highly efficient Suzuki coupling reactions. Reagent used for? ;Microwave-assisted copper(II)-catalyzed N-cyclopropylation1? ;Nickel- and copper-catalyzed Suzuki-Miyaura coupling reaction of arenes2? ;Palladacycle-catalyzed Suzuki-cross coupling of aryl halides with cyclopropylboronic acid3? ;Palladium(0)-catalyzed cyclopropane C-H bond functionalization4? ;Palladium-catalyzed decarboxylative coupling5? ;Palladium-catalyzed ligand-directed oxidative functionalization of cyclopropanes6? ;Palladium-catalyzed Suzuki coupling reaction7Reagent used in Preparation of? ;Diaryl ketones by arylation suzuki reaction

Technology Process of Cyclopropylboronic acid

There total 15 articles about Cyclopropylboronic acid 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: 92.0%

ethene (74-85-1) + formyl boronic acid + 3,5-dinitro-p-toluenesulfonylhydrazide → cyclopropylboronic acid (411235-57-9)

Guidance literature:

formyl boronic acid; 3,5-dinitro-p-toluenesulfonylhydrazide; In methanol; Reflux;

With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 0.5h;

ethene; Reagent/catalyst; Solvent; Further stages;

Reference yield: 86.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + pinacol vinylboronate (75927-49-0) → cyclopropylboronic acid (411235-57-9)

Guidance literature:

diazomethane; pinacol vinylboronate; With palladium diacetate; In tert-butyl methyl ether; Inert atmosphere;

With sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 0.05h; Reagent/catalyst; Temperature;

Reference yield: 82.0%

diiodomethane (75-11-6) + pinacol vinylboronate (75927-49-0) → cyclopropylboronic acid (411235-57-9)

Guidance literature:

diiodomethane; pinacol vinylboronate; With diethylzinc; at 60 ℃; for 12h; Inert atmosphere;

With 2,2'-iminobis[ethanol]; at 55 ℃; for 4h; Solvent; Temperature; Reagent/catalyst;

upstream raw materials:

cyclopropylmagnesium bromide

Trimethyl borate

C₅H₁₁BO₂

cyclopropylboronic acid methyliminodiacetic acid ester

Downstream raw materials:

1-cyclopropyl-3-methoxybenzene

2-nitro-1,4-dicyclopropylbenzene

1-cyclopropyl-4-benzonitrile

5-cyclopropyl-furan-2-carbaldehyde

Refernces

• 1、 Merchant, Rohan R.,Lopez, Jovan A.. "A General C(sp3)-C(sp3) Cross-Coupling of Benzyl Sulfonylhydrazones with Alkyl Boronic Acids". supporting information. p. 2271 - 2275. Retrieved 2020/03/13.
• 2、 -. "Method for preparing cyclopropylboronic acid on basis of carbene insertion process". Paragraph 0031; 0032; 0033; 0040-0047. . Retrieved 2019/01/08.