Ethyl 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Base Information

• Chemical Name: Ethyl 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
• CAS No.: 195062-62-5
• Molecular Formula: C15H21BO4
• Molecular Weight: 276.14
• Hs Code.: 29319090
• European Community (EC) Number: 671-672-6
• DSSTox Substance ID: DTXSID20370398
• Nikkaji Number: J902.925G
• Wikidata: Q72471421
• Mol file: 195062-62-5.mol

Synonyms:195062-62-5;Ethyl 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;4-Ethoxycarbonylphenylboronic acid pinacol ester;4-ETHOXYCARBONYLPHENYLBORONIC ACID, PINACOL ESTER;4-Carboethoxyphenylboronic acid pinacol ester;SCHEMBL3686298;ethyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;4-CARBOETHOXYPHENYLBORONIC;DTXSID20370398;AMY32787;VHA06262;MFCD03453659;AKOS015910396;ETHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2- DIOXABOROLAN-2-YL)BENZOATE;ETHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE;AB15515;DS-16238;CS-0028748;E1346;(4-ethoxycarbonylphenyl)boronic acid pinacol ester;A813782;J-012636;ethyl 4-(4,4,5,5 -tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;2-[4-(Ethoxycarbonyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid ethyl ester;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)benzoic acid ethyl ester;4-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-benzoic acid ethyl ester;ETHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE,MIN.97%

Chemical Property of Ethyl 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Chemical Property:

• Appearance/Colour: clear light yellow viscous liquid
• Vapor Pressure: 1.12E-05mmHg at 25°C
• Refractive Index: n20/D 1.5(lit.)
• Boiling Point: 370.2 °C at 760 mmHg
• Flash Point: 177.7 °C
• PSA: 44.76000
• Density: 1.075 g/cm³
• LogP: 2.16250
• Storage Temp.: Refrigerator (+4°C)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 276.1532893
• Heavy Atom Count: 20
• Complexity: 343

Purity/Quality:

99% ^*data from raw suppliers

4-Ethoxycarbonylphenylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)C(=O)OCC

Technology Process of Ethyl 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

There total 48 articles about Ethyl 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 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: 90.0%

Ethyl 4-bromobenzoate (5798-75-4) + bis(pinacol)diborane (73183-34-3) → ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (195062-62-5)

Guidance literature:

With pyridine; 9,10-Dicyanoanthracene; tert-butylammonium hexafluorophosphate(V); In acetonitrile; at 22 ℃; for 12h; Inert atmosphere; Electrolysis; Irradiation;

DOI:10.1021/jacs.9b10678

Reference yield: 90.0%

4-iodobenzoic acid ethyl ester (51934-41-9) + bis(pinacol)diborane (73183-34-3) → ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (195062-62-5)

Guidance literature:

With bis-(dimethylamino)methane; In water; acetone; acetonitrile; at -5 ℃; for 0.25h; Temperature; chemoselective reaction; UV-irradiation; Flow reactor;

DOI:10.1039/c5sc04521e

Reference yield: 90.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + Ethyl 4-bromobenzoate (5798-75-4) + bromocatecholborane (51901-85-0) + zinc (7440-66-6) → ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (195062-62-5)

Guidance literature:

With 3-chloroprop-1-ene; trifluoroacetic acid; cobalt(II) bromide; In acetonitrile; Zn dust (1.5 equiv., acid-activated) , CoBr2 (0.1 equiv.), stirred for 5min with allyl chloride (0.3 equiv.), a soln. of aryl halide (1 equiv.) and a soln. 1 equiv. of B compd. added at room temp., stirred for 30 mi n, tranesterificated with pinacol; hydrolized (NH4Cl), extd. (diethyl ether);

DOI:10.1039/b707056j

upstream raw materials:

4-iodobenzoic acid ethyl ester

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

Ethyl 4-bromobenzoate

p-(ethoxycarbonyl)phenyl triflate

Downstream raw materials:

ethyl 4-phenylbenzoate

(HOOCC₆H₄)2C₁₃H₆O

C₃₁H₂₄O₅

diethyl biphenyl-4,4'-dicarboxylate

Refernces

• 1、 Firth, James D.,Hammarback, L. Anders,Burden, Thomas J.,Eastwood, Jonathan B.,Donald, James R.,Horbaczewskyj, Chris S.,McRobie, Matthew T.,Tramaseur, Adam,Clark, Ian P.,Towrie, Michael,Robinson, Alan,Krieger, Jean-Philippe,Lynam, Jason M.,Fairlamb, Ian J. S.. "Light- and Manganese-Initiated Borylation of Aryl Diazonium Salts: Mechanistic Insight on the Ultrafast Time-Scale Revealed by Time-Resolved Spectroscopic Analysis". supporting information. p. 3979 - 3985. Retrieved 2021/02/03.
• 2、 Arman, Hadi D.,Dang, Hang. T.,Haug, Graham C.,He, Ru,Jin, Shengfei,Larionov, Oleg V.,Nguyen, Viet D.,Nguyen, Vu T.,Schanze, Kirk S.. "Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds". supporting information. . Retrieved 2020/02/04.