4,4,5,5-Tetramethyl-2-(naphthalen-1-ylmethyl)-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(naphthalen-1-ylmethyl)-1,3,2-dioxaborolane
• CAS No.: 475250-57-8
• Molecular Formula: C₁₇H₂₁BO₂
• Molecular Weight: 268.164
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID20460268
• Nikkaji Number: J1.857.028I
• Wikidata: Q82284265
• Mol file: 475250-57-8.mol

Synonyms:4,4,5,5-tetramethyl-2-(naphthalen-1-ylmethyl)-1,3,2-dioxaborolane;475250-57-8;MFCD22419278;SCHEMBL15547751;DTXSID20460268;VYMBZQMGIGIALJ-UHFFFAOYSA-N;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(1-naphthalenylmethyl)-;AKOS016007326;SY235332;1-Naphthylmethylboronic Acid Pinacol Ester;CS-0098270;T3626;T72507;(Naphthalen-1-ylmethyl)boronic Acid Pinacol Ester;(1-Naphthylmethyl)boronic acid pinacol ester, 95%;1-[(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]naphthalene

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

Chemical Property:

• PSA: 18.46000
• LogP: 4.28010
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 268.1634601
• Heavy Atom Count: 20
• Complexity: 337

Purity/Quality:

98%Min ^*data from raw suppliers

4,4,5,5-Tetramethyl-2-(naphthalen-1-ylmethyl)-1,3,2-dioxaborolane ^*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=CC3=CC=CC=C32
• Uses: (1-Naphthylmethyl)boronic acid pinacol ester is employed as a intermediate for chemical research.

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

There total 13 articles about 4,4,5,5-Tetramethyl-2-(naphthalen-1-ylmethyl)-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: 93.0%

1-Chloromethylnaphthalene (86-52-2) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(naphthalen-1-ylmethyl)-1,3,2-dioxaborolane (475250-57-8)

Guidance literature:

With potassium acetate; In toluene; toluene, 50°C, 24 h;

DOI:10.1016/S0022-328X(00)00470-8

Reference yield: 89.0%

1-naphthalene methanol (4780-79-4) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(naphthalen-1-ylmethyl)-1,3,2-dioxaborolane (475250-57-8)

Guidance literature:

With titanium(IV) isopropylate; tetrakis(acetonitrile)copper(II) tetrafluoroborate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tert-butyl methyl ether; at 100 ℃; for 12h; Reagent/catalyst; Temperature; Solvent; Catalytic behavior; Glovebox; Inert atmosphere;

DOI:10.1021/acs.orglett.7b00256

Reference yield: 62.0%

1-naphthyl triflate (99747-74-7) + 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) → 4,4,5,5-tetramethyl-2-(naphthalen-1-ylmethyl)-1,3,2-dioxaborolane (475250-57-8)

Guidance literature:

With tetra(n-butyl)ammonium hydroxide; palladium diacetate; triphenylphosphine; In 1,4-dioxane; water; at 20 ℃; Inert atmosphere;

DOI:10.1039/c6ra09959a

upstream raw materials:

1-Chloromethylnaphthalene

bis(pinacol)diborane

triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane

1-Methylnaphthalene

Refernces

• 1、 Wang, Chenglan,Zhou, Lu,Yang, Kai,Zhang, Feng,Song, Qiuling. "Photoinduced NaI-Promoted Radical Borylation of Alkyl Halides and Pseudohalides". . p. 1825 - 1830. Retrieved 2021/05/28.
• 2、 Mao, Lujia,Szabó, Kálmán J.,Marder, Todd B.. "Synthesis of Benzyl-, Allyl-, and Allenyl-boronates via Copper-Catalyzed Borylation of Alcohols". supporting information. p. 1204 - 1207. Retrieved 2017/03/14.