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

Base Information

• Chemical Name: Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
• CAS No.: 269410-00-6
• Molecular Formula: C15H21BO4
• Molecular Weight: 276.14
• Hs Code.: 2934999090
• European Community (EC) Number: 623-082-5
• DSSTox Substance ID: DTXSID70378804
• Nikkaji Number: J1.898.073H
• Wikidata: Q82168377
• Mol file: 269410-00-6.mol

Synonyms:269410-00-6;Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;3-Ethoxycarbonylphenylboronic acid, pinacol ester;3-Ethoxycarbonylphenylboronic acid pinacol ester;3-Carboethoxyphenylboronic acid pinacol ester;ethyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;(3-(ETHOXYCARBONYL)PHENYL)BORONIC ACID PINACOL ESTER;SCHEMBL1598557;3-CARBOETHOXYPHENYLBORONIC;DTXSID70378804;RQKGHIGGSFNVGW-UHFFFAOYSA-N;AMY13283;MFCD03093896;AKOS015894443;AB13283;CS-W000905;AS-32767;FT-0648011;EN300-1706326;A877086;J-016618;3-Ethoxycarbonylphenylboronic acid pinacol ester, 97%;3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE;3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ETHYL BENZOATE;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)benzoic acid ethyl ester;3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid ethyl ester;ETHYL-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE,MIN.97%

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

Chemical Property:

• Vapor Pressure: 6.21E-06mmHg at 25°C
• Melting Point: 40-44 °C(lit.)
• Refractive Index: 1.497
• Boiling Point: 378.6 °C at 760 mmHg
• Flash Point: 182.8 °C
• PSA: 44.76000
• Density: 1.07 g/cm³
• LogP: 2.16250
• Storage Temp.: Inert atmosphere,Room Temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 276.1532893
• Heavy Atom Count: 20
• Complexity: 351

Purity/Quality:

97% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

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

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

There total 14 articles about Ethyl 3-(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: 95.0%

ethyl 3-bromobenzoate (24398-88-7) + bis(pinacol)diborane (73183-34-3) → 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzoic acid ethyl ester (269410-00-6)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,2-dimethoxyethane; at 90 ℃; Inert atmosphere;

Reference yield: 95.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + ethyl 3-bromobenzoate (24398-88-7) + bromocatecholborane (51901-85-0) + zinc (7440-66-6) → 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzoic acid ethyl ester (269410-00-6)

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

Reference yield: 85.0%

3-iodobenzoic acid methyl ester (58313-23-8) + bis(pinacol)diborane (73183-34-3) → 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzoic acid ethyl ester (269410-00-6)

Guidance literature:

With potassium acetate; [Pd(dppf)Cl₂]*CH₂l2; In dimethyl sulfoxide; at 80 - 90 ℃; for 4.5h;

DOI:10.1002/hlca.200390055

upstream raw materials:

benzoic acid ethyl ester

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

3-iodobenzoic acid methyl ester

bis(pinacol)diborane

Downstream raw materials:

tetraethyl 3,3',3'',3'''-(1,1'-biphenyl-3,3',5,5'-tetrayl)tetrakis(benzenecarboxylate)

2-(3,4,5-trimethoxyphenylamino)-6-(ethyl-3-benzoate)pyrazine

(Z)-ethyl 3-(3-methoxy-3-oxo-1-(2-oxopyrrolidin-1-yl)prop-1-en-1-yl)benzoate

C₂₅H₂₀F₃NO₄