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

Base Information

• Chemical Name: 2-(4-Fluorobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 243145-83-7
• Molecular Formula: C13H18 B F O2
• Molecular Weight: 236.094
• Hs Code.: 2934999090
• European Community (EC) Number: 833-134-0
• DSSTox Substance ID: DTXSID80454345
• Nikkaji Number: J1.147.023H
• Wikidata: Q72479294
• Mol file: 243145-83-7.mol

Synonyms:243145-83-7;2-(4-Fluorobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-FLUOROBENZYLBORONIC ACID PINACOL ESTER;2-[(4-fluorophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;MFCD10698519;1,3,2-Dioxaborolane, 2-[(4-fluorophenyl)methyl]-4,4,5,5-tetramethyl-;(4-FLUOROBENZYL)BORONIC ACID PINACOL ESTER;SCHEMBL13255385;DTXSID80454345;RLTRQJNDILQGNA-UHFFFAOYSA-N;AKOS016007337;AB62284;CS-W019272;DS-17309;SY108397;FT-0746414;EN300-129603;Z1625061413

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

Chemical Property:

• Boiling Point: 275 ºC
• Flash Point: 120 ºC
• PSA: 18.46000
• Density: 1.04
• LogP: 3.26600
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 236.1383881
• Heavy Atom Count: 17
• Complexity: 257

Purity/Quality:

99% ^*data from raw suppliers

4-Fluorobenzylboronicacidpinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)CC2=CC=C(C=C2)F

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

There total 13 articles about 2-(4-Fluorobenzyl)-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: 97.0%

4-Fluorobenzyl bromide (459-46-1) + bis(pinacol)diborane (73183-34-3) → 2-[(4-fluorophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (243145-83-7)

Guidance literature:

With lithium tert-butoxide; In N,N-dimethyl-formamide; at 30 ℃; for 2h; under 760.051 Torr; Irradiation;

DOI:10.1016/j.jcat.2021.01.019

Reference yield: 93.0%

1-chloromethyl-4-fluorobenzene (352-11-4) + bis(pinacol)diborane (73183-34-3) → 2-[(4-fluorophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (243145-83-7)

Guidance literature:

With iron(III)-acetylacetonate; magnesium; In tetrahydrofuran; at 0 ℃; for 3h; Inert atmosphere;

Reference yield: 83.0%

1-Bromo-4-fluorobenzene (460-00-4) + 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane (78782-17-9) → 2-[(4-fluorophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (243145-83-7)

Guidance literature:

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium hydroxide; In 1,4-dioxane; water; at 25 ℃; for 2h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/ol201115k

upstream raw materials:

tributyl(4-fluorophenyl)stannane

pinacol (bromomethyl)boronate

4-Fluorobenzyl bromide

bis(pinacol)diborane

Downstream raw materials:

C₁₇H₁₂BrClFNO

C₁₈H₁₅BrFNO

C₂₇H₂₈FN₃O₃

1-ethyl-4-fluorobenzene

Refernces

• 1、 Giroux, André. "Synthesis of benzylic boronates via palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with benzylic halides". . p. 233 - 235. Retrieved 2003.
• 2、 Yang, Ling,Tan, Dong-Hang,Fan, Wen-Xin,Liu, Xu-Ge,Wu, Jia-Qiang,Huang, Zhi-Shu,Li, Qingjiang,Wang, Honggen. "Photochemical Radical C–H Halogenation of Benzyl N-Methyliminodiacetyl (MIDA) Boronates: Synthesis of α-Functionalized Alkyl Boronates". supporting information. p. 3454 - 3458. Retrieved 2020/12/17.
• 3、 Huang, Chia-Yu,Li, Chao-Jun,Li, Jianbin,Qiu, Zihang,Wang, Haining. "Metal-Free Direct Deoxygenative Borylation of Aldehydes and Ketones". . p. 13011 - 13020. Retrieved 2020/09/01.