2-(4-Fluorophenethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(4-Fluorophenethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 1065498-70-5
• Molecular Formula: C₁₄H₂₀BFO₂
• Molecular Weight: 250.121
• European Community (EC) Number: 875-475-8
• DSSTox Substance ID: DTXSID60469452
• Nikkaji Number: J3.073.423H
• Wikidata: Q82297183
• Mol file: 1065498-70-5.mol

Synonyms:2-(4-Fluorophenethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;1065498-70-5;2-[2-(4-fluorophenyl)ethyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;AGN-PC-00CP71;SCHEMBL2123915;DTXSID60469452;EN300-12596889;Z2049747163

Chemical Property of 2-(4-Fluorophenethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 250.1540382
• Heavy Atom Count: 18
• Complexity: 270

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)CCC2=CC=C(C=C2)F

Technology Process of 2-(4-Fluorophenethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 28 articles about 2-(4-Fluorophenethyl)-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%

para-fluorostyrene (405-99-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(2-(4-fluorophenyl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1065498-70-5)

Guidance literature:

With calcium chloride; In chloroform-d1; at 110 ℃; for 12h; Glovebox;

Reference yield: 99.0%

para-fluorostyrene (405-99-2) + bis(pinacol)diborane (73183-34-3) → 2-(2-(4-fluorophenyl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1065498-70-5)

Guidance literature:

With potassium tert-butylate; iron(II) chloride; tert-butyl alcohol; In tetrahydrofuran; at 65 ℃; for 12h; Inert atmosphere; Schlenk technique; Green chemistry;

DOI:10.1039/c5ra14869c

Reference yield: 89.0%

(2-bromoethyl)-4-fluorobenzene (332-42-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(2-(4-fluorophenyl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1065498-70-5)

Guidance literature:

With chromium chloride; aluminium; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; at 80 ℃; for 15h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.organomet.1c00171

upstream raw materials:

para-fluorostyrene

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

1-ethynyl-4-fluorobenzene

2-(1-chloro-2-(4-fluorophenyl)vinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Downstream raw materials:

trifluoro(4-fluorophenethyl)-λ⁴-borane potassium salt

1-(4-fluorophenyl)-2-phenylethane

Refernces

• 1、 Poitras, Andrew M.,Oliemuller, Leah K.,Hatzis, Gregory P.,Thomas, Christine M.. "Highly Selective Hydroboration of Terminal Alkenes Catalyzed by a Cobalt Pincer Complex Featuring a Central Reactive N-Heterocyclic Phosphido Fragment". . p. 1025 - 1031. Retrieved 2021.
• 2、 Li, Jiang-Fei,Wei, Zhen-Zhong,Wang, Yong-Qiu,Ye, Mengchun. "Base-free nickel-catalyzed hydroboration of simple alkenes with bis(pinacolato)diboron in an alcoholic solvent". . p. 4498 - 4502. Retrieved 2017.
• 3、 Kamei, Toshiyuki,Nishino, Sohshi,Shimada, Toyoshi. "Ni-catalyzed hydroboration and hydrosilylation of olefins with diboron and silylborane". . p. 2896 - 2899. Retrieved 2018.
• 4、 Fu, Aiping,Li, Chao,Luo, Meiming,Zeng, Xiaoming,Zhao, Lixing. "Chromium-Catalyzed Borylative Coupling of Aliphatic Bromides with Pinacolborane by Hydrogen Evolution". . p. 2204 - 2208. Retrieved 2021.
• 5、 Ang, Nate W. J.,Buettner, Cornelia S.,Docherty, Scott,Bismuto, Alessandro,Carney, Jonathan R.,Docherty, Jamie H.,Cowley, Michael J.,Thomas, Stephen P.. "Borane-Catalysed Hydroboration of Alkynes and Alkenes". . p. 803 - 808. Retrieved 2018.
• 6、 Wen, Yanmei,Xie, Jianying,Deng, Chunmei,Li, Chaode. "Selective synthesis of alkylboronates by copper(I)-catalyzed borylation of allyl or vinyl arenes". . p. 4142 - 4147. Retrieved 2015.
• 7、 Bismuto, Alessandro,Cowley, Michael J.,Thomas, Stephen P.. "Aluminum-Catalyzed Hydroboration of Alkenes". . p. 2001 - 2005. Retrieved 2018.
• 8、 Pecak, Jan,Fleissner, Sarah,Veiros, Luis F.,Pittenauer, Ernst,St?ger, Berthold,Kirchner, Karl. "Synthesis and Catalytic Reactivity of Cobalt Pincer Nitrosyl Hydride Complexes". . p. 278 - 285. Retrieved 2021.
• 9、 Kumar, Gobbilla Sai,Moorthy, Shruti,Karmakar, Himadri,Singh, Saurabh Kumar,Panda, Tarun K.. "Neosilyllithium-Catalyzed Hydroboration of Alkynes and Alkenes in the Presence of Pinacolborane (HBpin)". supporting information. . Retrieved 2021/11/13.
• 10、 Zhang, Yahui,Zhao, Xiangyu,Bi, Ce,Lu, Wenqi,Song, Mengyuan,Wang, Dongdong,Qing, Guangyan. "Selective electrocatalytic hydroboration of aryl alkenes". supporting information. p. 1691 - 1699. Retrieved 2021/03/09.