4-Formyl-2-methylphenylboronic acid

Base Information

• Chemical Name: 4-Formyl-2-methylphenylboronic acid
• CAS No.: 156428-81-8
• Molecular Formula: C8H9BO3
• Molecular Weight: 163.96600
• Hs Code.: 2931900090
• European Community (EC) Number: 871-113-8
• DSSTox Substance ID: DTXSID30438832
• Wikidata: Q82254666
• Mol file: 156428-81-8.mol

Synonyms:156428-81-8;4-FORMYL-2-METHYLPHENYLBORONIC ACID;(4-Formyl-2-methylphenyl)boronic acid;(4-Formyl-2-methylphenyl)boronicacid;Boronic acid, (4-formyl-2-methylphenyl)-;SCHEMBL789495;DTXSID30438832;ORHODDYPZMCLBU-UHFFFAOYSA-N;MFCD09839115;2-methyl-4-formylbenzene boronic acid;AKOS006328764;AB53513;AM90060;BS-27406;CS-0061263;EN300-316483;W16721;A849007

Chemical Property of 4-Formyl-2-methylphenylboronic acid

Chemical Property:

• Melting Point: 140 - 143°C
• Boiling Point: 357.7±52.0 °C(Predicted)
• PKA: 7.42±0.58(Predicted)
• PSA: 57.53000
• Density: 1.20±0.1 g/cm3(Predicted)
• LogP: -0.51270
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 164.0644743
• Heavy Atom Count: 12
• Complexity: 160

Purity/Quality:

98%min ^*data from raw suppliers

4-Formyl-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=C(C=C1)C=O)C)(O)O
• Uses: 4-Formyl-2-methylphenylboronic acid

Technology Process of 4-Formyl-2-methylphenylboronic acid

There total 2 articles about 4-Formyl-2-methylphenylboronic 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:

Triisopropyl borate (5419-55-6) + 2-(4-bromo-3-methylphenyl)-1,3-dioxolane + water (7732-18-5) → (4-formyl-2-methylphenyl)boronic acid (156428-81-8)

Guidance literature:

2-(4-bromo-3-methylphenyl)-1,3-dioxolane; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

water; With hydrogenchloride; for 3h;

Reference yield:

3-methyl-4-bromobenzaldehyde (78775-11-8) → (4-formyl-2-methylphenyl)boronic acid (156428-81-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: toluene-4-sulfonic acid / toluene / 20 h / Dean-Stark; Reflux

2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

2.3: 3 h

With n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; toluene;

Reference yield: 83.0%

3-(5-bromothiophen-2-yl)-2,5-bis(2-ethylhexyl)-6-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)dione (1308671-90-0) + (4-formyl-2-methylphenyl)boronic acid (156428-81-8) → 4-(5-(2,5-bis(2-ethylhexyl)-3,6-dioxo-4-(thiophen-2-yl)-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrol-1-yl)thiophen-2-yl)-3-methylbenzaldehyde

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In tetrahydrofuran; at 65 ℃; Inert atmosphere;

upstream raw materials:

Triisopropyl borate

water

3-methyl-4-bromobenzaldehyde

Refernces