4,4,5,5-Tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolane
• CAS No.: 174090-36-9
• Molecular Formula: C14H21BO2
• Molecular Weight: 232.131
• Hs Code.: 2934999090
• European Community (EC) Number: 877-464-3
• DSSTox Substance ID: DTXSID80464767
• Nikkaji Number: J1.113.135B
• Mol file: 174090-36-9.mol

Synonyms:4,4,5,5-tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolane;174090-36-9;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(1-phenylethyl)-;SCHEMBL12137184;DTXSID80464767;AKOS016006623;AB62314;FT-0689742;EN300-299716;Z2049704755;257298-93-4

Chemical Property of 4,4,5,5-Tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolane

Chemical Property:

• PSA: 18.46000
• LogP: 3.51700
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 232.1634601
• Heavy Atom Count: 17
• Complexity: 253

Purity/Quality:

98%min ^*data from raw suppliers

4,4,5,5-Tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolane 95+% ^*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)C(C)C2=CC=CC=C2

Technology Process of 4,4,5,5-Tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolane

There total 57 articles about 4,4,5,5-Tetramethyl-2-(1-phenylethyl)-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%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4,4,5,5-tetramethyl-2-(1-phenyl-ethyl)-[1,3,2]dioxaborolane (174090-36-9) + 4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolane (165904-22-3)

Guidance literature:

With potassium tert-butylate; copper(l) chloride; In toluene; 60°C, 7 h;

DOI:10.1002/anie.200902015

Reference yield: 98.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4,4,5,5-tetramethyl-2-(1-phenyl-ethyl)-[1,3,2]dioxaborolane (174090-36-9)

Guidance literature:

With C₃₄H₃₀NiO₆; potassium; In tetrahydrofuran; at 25 ℃; for 1h; Reagent/catalyst; Solvent; regioselective reaction; Inert atmosphere;

DOI:10.1039/c9dt00468h

Reference yield: 94.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → ethylbenzene (100-41-4,27536-89-6) + 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane (83947-56-2) + 4,4,5,5-tetramethyl-2-(1-phenyl-ethyl)-[1,3,2]dioxaborolane (174090-36-9) + 4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolane (165904-22-3)

Guidance literature:

chloro(1,5-cyclooctadiene)rhodium(I) dimer; In toluene; pinacolborane and vinylarene were added to a mixt. of Rh-complex in toluene under Ar, the mixt. was stirred at room temp. for 4 h; diluted with toluene, washed with water, dried over MgSO4, evapd., distilled with Kugelrohr or chromy. on silica gel;

DOI:10.1246/bcsj.75.825

upstream raw materials:

styrene

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

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

bis(pinacol)diborane

Downstream raw materials:

(S)-2-Phenylpropionic acid

(R)-2-Phenylpropionic acid

(RS)-2-phenyl-1-propanol

3-phenyl-1-butanol

Refernces

• 1、 Won, Jiyeon,Noh, Dongwan,Yun, Jaesook,Lee, Jin Yong. "Catalytic activity of phosphine - Copper complexes for hydroboration of styrene with pinacolborane: Experiment and theory". . p. 12112 - 12115. Retrieved 2010.
• 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、 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.