4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde

Base Information

• Chemical Name: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde
• CAS No.: 846023-58-3
• Molecular Formula: C₁₁H₁₅BO₄
• Molecular Weight: 222.049
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID50393530
• Wikidata: Q82192328
• Mol file: 846023-58-3.mol

Synonyms:846023-58-3;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde;5-FORMYLFURAN-3-BORONIC ACID PINACOL ESTER;2-Formylfuran-4-boronic acid pinacol ester;MFCD06657890;SCHEMBL4131687;DTXSID50393530;YHEMDDZDHYKQGZ-UHFFFAOYSA-N;4-(tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde;WIB02358;AKOS015968925;AB25737;AS-55768;SY064812;CS-0046253;FT-0726277;D72732;A864055

Chemical Property of 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde

Chemical Property:

• Boiling Point: 338.1 °C at 760 mmHg
• Flash Point: 158.3 °C
• PSA: 48.67000
• Density: 1.1 g/cm³
• LogP: 1.39130
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 222.1063391
• Heavy Atom Count: 16
• Complexity: 274

Purity/Quality:

99%, ^*data from raw suppliers

2-Formylfuran-4-boronicacidpinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde

There total 3 articles about 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde 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: 79.5%

→ 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-furancarboxaldehyde (846023-58-3)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; Inert atmosphere;

Reference yield: 66.0%

C9H11BrNO(1+)*ClO4(1-) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-furancarboxaldehyde (846023-58-3)

Guidance literature:

C₉H₁₁BrNO⁽¹⁺⁾*ClO₄^(1-); With chloro-bis(dimethylamino)borane; lithium; In tetrahydrofuran; at -10 - 0 ℃;

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; Solvent; Heating;

Reference yield:

furfural (98-01-1) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-furancarboxaldehyde (846023-58-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: perchloric acid / toluene; 1,4-dioxane / Reflux

2.1: N-Bromosuccinimide; acetonitrile boron trifluoride complex / acetonitrile / Reflux

3.1: chloro-bis(dimethylamino)borane; lithium / tetrahydrofuran / -10 - 0 °C

3.2: Heating

With N-Bromosuccinimide; perchloric acid; chloro-bis(dimethylamino)borane; acetonitrile boron trifluoride complex; lithium; In tetrahydrofuran; 1,4-dioxane; toluene; acetonitrile;

upstream raw materials:

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

furfural

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