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

Base Information

• Chemical Name: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid
• CAS No.: 180516-87-4
• Molecular Formula: C13H17BO4
• Molecular Weight: 248.087
• Hs Code.: 29163990
• European Community (EC) Number: 671-851-9
• DSSTox Substance ID: DTXSID90370401
• Nikkaji Number: J1.794.764H
• Wikidata: Q72515573
• Mol file: 180516-87-4.mol

Synonyms:180516-87-4;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid;4-Carboxyphenylboronic acid pinacol ester;4-Carboxylphenylboronic acid pinacol ester;4-carboxyphenylboronic acid, pinacol ester;MFCD01863710;4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid;BENZOIC ACID, 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-;4-carboxyphenylboronic acid,pinacol ester;4-carboxybenzeneboronic acid pinacol ester;2-(4-Carboxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-Carboxyphenylboronicacidpinacolester;SCHEMBL105188;DTXSID90370401;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid;4-carboxyphenylboronic acid pinacolate;AKOS015915428;AC-6993;AS-2258;CS-W000887;4-BORONOBENZOIC ACID PINACOL ESTER;SY002371;(4-carboxyphenyl)boronic acid pinacol ester;4-carboxybenzeneboronic acid, pinacol ester;(4-carboxyphenyl)boronic acid, pinacol ester;A4001;AM20050295;FT-0643741;T2841;4-carboxybenzeneboronic acid pinacolcyclicester;EN300-99184;4-Carboxylphenylboronic acid pinacol ester, 97%;4-carboxyphenylboronic acid, pinacol cyclic ester;J-011531;J-513429;Z1324655439;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoicacid;4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoic acid;4-(4,4,5,5-tetrameyl-1,3,2-dioxaborolan-2-yl)benzoic acid;4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-benzoic acid;4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)benzoic acid;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-benzoic acid;4-(hydroxy(3-hydroxy-2,3-dimethylbutan-2-yloxy)boryl)benzoic acid

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

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 1.92E-06mmHg at 25°C
• Melting Point: 228-231 °C(lit.)
• Refractive Index: 1.521
• Boiling Point: 379.7 °C at 760 mmHg
• PKA: 4.09±0.10(Predicted)
• Flash Point: 183.4 °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: 316

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)C(=O)O
• Uses: 4-Carboxybenzeneboronic acid pinacol ester is used to improvement of transition metal-mediated carbon-carbon as well as carbon-heteroatom cross-coupling reactions as a labeling feature with the focus on the preparation of radio labeled compounds for molecular imaging.

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

There total 21 articles about 4-(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: 100.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 4-carboxyphenylboronic acid (14047-29-1) → 4-carboxyphenylboronic acid pinacol ester (180516-87-4)

Guidance literature:

In tetrahydrofuran; toluene;

DOI:10.1081/SCC-120006031

Reference yield: 87.0%

H2O*CHLiO2 + 2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (73852-88-7) → 4-carboxyphenylboronic acid pinacol ester (180516-87-4)

Guidance literature:

With formic acid; 1,3-bis-(diphenylphosphino)propane; nickel(II) acetate tetrahydrate; acetic anhydride; In tetrahydrofuran; at 100 ℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1039/d0cc01363c

Reference yield: 80.0%

4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) + bis(pinacol)diborane (73183-34-3) → 4-carboxyphenylboronic acid pinacol ester (180516-87-4)

Guidance literature:

4-amino-benzoic acid; With hydrogenchloride; sodium nitrite; In water; at 0 - 5 ℃;

With sodium tetrafluoroborate; In water; at 5 ℃;

bis(pinacol)diborane; With copper(I) bromide; In water; acetonitrile; at 20 ℃; for 3h;

DOI:10.1055/s-0031-1290960

upstream raw materials:

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

4-carboxyphenylboronic acid

4-formylphenylboronic acid,

4-iodobenzoic acid

Downstream raw materials:

3'‐methyl‐(1,1'‐biphenyl)‐4‐carboxylic acid

4-(8-(2,6-difluorophenyl)-2-{[2-(dimethylamino)ethyl]amino}-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl)benzoic acid

N-(2-pyrrolidin-1-yl-ethyl)-4-(4,4,5,5-tetramethyl-[1,2,3]dioxaborolan-2-yl)-benzamide

1-cyclobutyl-4-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbonyl}hexahydro-1H-1,4-diazepine