3-Borono-4-methylbenzoic acid

Base Information

• Chemical Name: 3-Borono-4-methylbenzoic acid
• CAS No.: 170230-88-3
• Molecular Formula: C8H9 B O4
• Molecular Weight: 179.968
• Hs Code.: 2931900090
• European Community (EC) Number: 803-125-6
• DSSTox Substance ID: DTXSID80597069
• Nikkaji Number: J2.686.137C
• Wikidata: Q82492540
• Mol file: 170230-88-3.mol

Synonyms:3-Borono-4-methylbenzoic acid;170230-88-3;5-CARBOXY-2-METHYLPHENYLBORONIC ACID;5-Carboxy-2-methylphenylboronicacid;(2-Methyl-5-Carboxyphenyl)boronic acid;3-(DIHYDROXYBORANYL)-4-METHYLBENZOIC ACID;Benzoic acid,3-borono-4-methyl-;3-Borono-4-methylbenzoicacid;SCHEMBL379961;AMY3489;DTXSID80597069;OEGYTHZGLBLPCE-UHFFFAOYSA-N;BCP13675;VGA23088;MFCD08061639;AKOS006287158;SB34200;DS-15229;DB-000884;CS-0043000;EN300-303789;A852975

Chemical Property of 3-Borono-4-methylbenzoic acid

Chemical Property:

• Melting Point: 157-167 °C
• Boiling Point: 446.8±55.0 °C(Predicted)
• PKA: 4.38±0.10(Predicted)
• PSA: 77.76000
• Density: 1.34±0.1 g/cm3(Predicted)
• LogP: -0.62700
• Storage Temp.: Room temperature.
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 180.0593889
• Heavy Atom Count: 13
• Complexity: 195

Purity/Quality:

99% ^*data from raw suppliers

5-Carboxy-2-methylphenylboronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(C=CC(=C1)C(=O)O)C)(O)O
• Uses: 5-Carboxy-2-methylphenylboronic Acid acts as a reagent in the synthesis of pyrazolopyridinone-based p38 MAP kinase inhibitor

Technology Process of 3-Borono-4-methylbenzoic acid

There total 3 articles about 3-Borono-4-methylbenzoic 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: 54.0%

3-iodo-4-toluic acid (82998-57-0) → 3-carboxy-6-methylphenylboronic acid (170230-88-3) + C16H15BO5 + p-Toluic acid (99-94-5)

Guidance literature:

3-iodo-4-toluic acid; With isopropylmagnesium chloride; In tetrahydrofuran; at -50 ℃; for 1h; Inert atmosphere;

With Triisopropyl borate; In tetrahydrofuran; at -40 - -10 ℃; Inert atmosphere;

With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃; pH=1 - 2; Inert atmosphere;

DOI:10.1021/jo802186m

Reference yield: 54.0%

Trimethyl borate (121-43-7,63156-11-6) + 3-bromo-4-methylbenzoic acid (7697-26-9) → 3-carboxy-6-methylphenylboronic acid (170230-88-3)

Guidance literature:

3-bromo-4-methylbenzoic acid; With n-butyllithium; In tetrahydrofuran; hexane; at -100 ℃; for 2h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; hexane; at -100 - 20 ℃; Inert atmosphere;

With hydrogenchloride; water; In diethyl ether; Inert atmosphere;

DOI:10.1002/anie.200906620

Reference yield:

4-methyl-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoic acid (515131-35-8) → 3-carboxy-6-methylphenylboronic acid (170230-88-3)

Guidance literature:

With hydrogenchloride; sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 8h;

upstream raw materials:

3-iodo-4-toluic acid

Trimethyl borate

3-bromo-4-methylbenzoic acid

4-methyl-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoic acid

Downstream raw materials:

3-(1-hydroxyphthalazin-6-yl)-4-methylbenzoic acid

p-Toluic acid

4-methyl-3-(1-morpholinophthalazin-6-yl)benzoic acid

4-(phthalazin-1-yl)morpholine

Refernces

• 1、 -. "BCR-ABL TYROSINE-KINASE LIGANDS CAPABLE OF DIMERIZING IN AN AQUEOUS SOLUTION, AND METHODS OF USING SAME". Paragraph 00311; 00312. . Retrieved 2015/07/23.
• 2、 Pal, Arnab,Berube, Marie,Hall, Dennis G.. "Design, synthesis, and screening of a library of peptidyl bis(boroxoles) as oligosaccharide receptors in water: Identification of a receptor for the tumor marker TF-antigen disaccharide". supporting information; experimental part. p. 1492 - 1495. Retrieved 2010/06/16.