3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

Base Information

• Chemical Name: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid
• CAS No.: 269409-73-6
• Molecular Formula: C13H17BO4
• Molecular Weight: 248.087
• Hs Code.: 29310099
• European Community (EC) Number: 671-852-4
• DSSTox Substance ID: DTXSID10370423
• Nikkaji Number: J2.677.400D
• Wikidata: Q72515676
• ChEMBL ID: CHEMBL573441
• Mol file: 269409-73-6.mol

Synonyms:269409-73-6;3-Carboxyphenylboronic acid pinacol ester;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid;3-carboxyphenylboronic acid, pinacol ester;MFCD03411930;BENZOIC ACID, 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-;(3-Carboxyphenyl)boronic acid, pinacol ester;SCHEMBL488896;3-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid;CHEMBL573441;DTXSID10370423;OPWAPCOSDAFWFB-UHFFFAOYSA-N;BCP27288;AKOS015915430;AB14278;AC-2891;AS-2286;CS-W003049;3-BORONOBENZOIC ACID PINACOL ESTER;SY003278;(3-Carboxyphenyl)boronic acid pinacol ester;AM20050468;FT-0644218;T3162;3-Carboxyphenylboronic acid pinacol ester, 97%;EN300-1706364;J-512162;Z1741960619;2-(3-Carboxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoicacid;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-benzoic acid;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)benzoic acid

Chemical Property of 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

Chemical Property:

• Appearance/Colour: almost white to light beige crystalline powder
• Vapor Pressure: 5.95E-07mmHg at 25°C
• Melting Point: 206-211 °C
• Refractive Index: 1.521
• Boiling Point: 395.121 °C at 760 mmHg
• PKA: 4.20±0.10(Predicted)
• Flash Point: 192.763 °C
• PSA: 55.76000
• Density: 1.15 g/cm³
• LogP: 1.68400
• Storage Temp.: Refrigerator (+4°C)
• Water Solubility.: Insoluble
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 248.1219892
• Heavy Atom Count: 18
• Complexity: 324

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

There total 13 articles about 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid 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: 92.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 3-Carboxyphenylboronic acid (25487-66-5) → 3-carboxyphenylboronic acid pinacol ester (269409-73-6)

Guidance literature:

In toluene; for 12h; Reflux; Inert atmosphere;

DOI:10.1039/d0ob02587a

Reference yield: 89.0%

m-bromobenzoic acid (585-76-2) + bis(pinacol)diborane (73183-34-3) → 3-carboxyphenylboronic acid pinacol ester (269409-73-6)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 110 ℃; Inert atmosphere;

Reference yield: 85.0%

bis(pinacol)diborane (73183-34-3) + 3-Iodobenzoic acid (618-51-9) → 3-carboxyphenylboronic acid pinacol ester (269409-73-6)

Guidance literature:

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

DOI:10.1039/c5sc04521e

upstream raw materials:

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

3-Iodobenzoic acid

meta-aminobenzoic acid

bis(pinacol)diborane

Downstream raw materials:

morpholin-4-yl-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxa-borolan-2-yl)-phenyl]-methanone

tert-butyl 4-(-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl)-1,4-diazepane-1-carboxylate

tert-butyl 4-(3-(8-bromo-[1,2,4]-triazolo[1,5-a]pyridin-6-yl)benzoyl)-1,4-diazepane-1-carboxylate

tert-butyl 4-(3-(8-(5,6-dimethoxypyridin-2-ylamino)-[1,2,4]-triazolo[1,5-a]pyridin-6-yl)benzoyl)-1,4-diazepane-1-carboxylate