(3-Formyloxyphenyl)boronic acid

Base Information

• Chemical Name: (3-Formyloxyphenyl)boronic acid
• CAS No.: 25487-66-5
• Molecular Formula: C7H7BO4
• Molecular Weight: 165.941
• Hs Code.: 29163990
• DSSTox Substance ID: DTXSID20948374
• Wikidata: Q72515667
• Mol file: 25487-66-5.mol

Synonyms:(3-formyloxyphenyl)boronic acid;1309981-04-1;[3-(formyloxy)phenyl]boronic acid;(3-(Formyloxy)phenyl)boronic acid;Benzeneboronic acid, m-carboxy-;m-Carboxybenzeneboronic acid;BRN 2967400;SCHEMBL479803;(3-(Formyloxy)phenyl)boronicacid;DTXSID20948374;AKOS015920429

Chemical Property of (3-Formyloxyphenyl)boronic acid

Chemical Property:

• Appearance/Colour: off-white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 243-247 °C(lit.)
• Refractive Index: 1.585
• Boiling Point: 434.512 °C at 760 mmHg
• PKA: 4.21±0.10(Predicted)
• Flash Point: 216.585 °C
• PSA: 77.76000
• Density: 1.406 g/cm³
• LogP: -0.93540
• Storage Temp.: 0-6°C
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Water Solubility.: 2.5 g/100 mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 166.0437389
• Heavy Atom Count: 12
• Complexity: 150

Purity/Quality:

99.0%min by HPLC ^*data from raw suppliers

3-Carboxyphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CC=C1)OC=O)(O)O
• Uses: 3-Carboxyphenylboronic acid is used in Suzuki coupling chemistry.1,2,3 suzuki reaction 3-Carboxyphenylboronic acid can be used as a substrate in the preparation of:Biaryl derivatives by reacting with bromoaniline through the Suzuki-Miyaura coupling reaction.Boronic acid-functionalized block copolymer.1H-Imidazo[1,2-a]quinoxaline derivatives.

Technology Process of (3-Formyloxyphenyl)boronic acid

There total 11 articles about (3-Formyloxyphenyl)boronic 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: 99.0%

3-carboxyphenylboronic acid pinacol ester (269409-73-6) + dihydroxy-methyl-borane (13061-96-6) → 3-Carboxyphenylboronic acid (25487-66-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃;

DOI:10.1021/acs.orglett.9b00584

Reference yield: 89.0%

(3‐cyanophenyl)boronic acid (150255-96-2) → 3-Carboxyphenylboronic acid (25487-66-5)

Guidance literature:

(3‐cyanophenyl)boronic acid; With potassium hydroxide; In ethylene glycol; at 175 ℃; for 3h;

With hydrogenchloride; In water; ethylene glycol; pH=2 - 3;

Reference yield: 61.2%

potassium permanganate (7722-64-7) + m-tolylboronic acid (17933-03-8) → 3-Carboxyphenylboronic acid (25487-66-5)

Guidance literature:

With sodium hydroxide; In water; at 30 - 40 ℃; Temperature;

upstream raw materials:

m-tolylboronic acid

carbon dioxide

1,3-Diiodobenzene

(3‐cyanophenyl)boronic acid

Downstream raw materials:

[3-(ethoxycarbonyl)phenyl]boronic acid

3-(di-n-butylamino)carbonylphenylboronic acid

3-phenylaminocarbonylphenylboronic acid

3-(8-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-benzoic acid

Refernces

• 1、 -. "A process for preparing carboxyl boric acid". Paragraph 0027; 0028. . Retrieved 2017/08/25.
• 2、 Erb, William,Hellal, Akila,Albini, Mathieu,Rouden, Jacques,Blanchet, Jerome. "An easy route to (hetero)arylboronic acids". supporting information. p. 6608 - 6612. Retrieved 2014/06/09.