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

Base Information

• Chemical Name: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde
• CAS No.: 273731-82-1
• Molecular Formula: C11H15BO4
• Molecular Weight: 222.049
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60682200
• Nikkaji Number: J3.558.078F
• Wikidata: Q82606504
• Mol file: 273731-82-1.mol

Synonyms:273731-82-1;5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde;5-formylfuran-2-boronic acid, pinacol ester;5-Formylfuran-2-boronic acid pinacol ester;SCHEMBL15649689;DTXSID60682200;VSQZZPPWTRWPTM-UHFFFAOYSA-N;MFCD16295105;AKOS016000333;AT16190;SB60876;PS-13128;2-Formylfuran-5-boronic acid pinacol ester;CS-0174951;J3.558.078F;EN300-314471;A876955;5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)furan-2-carbaldehyde;5-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)FURAN-2-CARBALDEHYDE

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

Chemical Property:

• Boiling Point: 338.1±27.0 °C(Predicted)
• PSA: 48.67000
• Density: 1.10±0.1 g/cm3(Predicted)
• LogP: 1.39130
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• 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:

98.5% ^*data from raw suppliers

5-Formylfuran-2-boronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(O2)C=O
• Uses: 5-Formylfuran-2-boronic Acid Pinacol Ester could be useful for the diastereoselective synthesis of cyclic peptide macrocycles via Petasis borono-Mannich reaction

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

There total 3 articles about 5-(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: 88.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 5-formylfurane-2-boronic acid (27329-70-0) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde (273731-82-1)

Guidance literature:

In toluene; at 100 ℃;

DOI:10.1002/chem.201500835

Reference yield: 23.0%

5-bromo-2-furancarboxaldehyde (1899-24-7) + bis(pinacol)diborane (73183-34-3) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde (273731-82-1)

Guidance literature:

With N',N''-bisoctadecyl-N-boc-L-glutamic acid diamide; N-ethyl-N,N-diisopropylamine; In water; acetonitrile; at 23 ℃; for 5h; Irradiation;

DOI:10.1021/acs.orglett.1c00451

Reference yield:

2-(diethoxymethyl)furan (13529-27-6) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde (273731-82-1)

Guidance literature:

2-(diethoxymethyl)furan; With n-butyllithium; In 1,2-dimethoxyethane; hexane; at -50 ℃; for 5h; Inert atmosphere;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In 1,2-dimethoxyethane; hexane; at -40 - 20 ℃; for 6.5h; Inert atmosphere;

upstream raw materials:

2-(diethoxymethyl)furan

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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

5-formylfurane-2-boronic acid

Downstream raw materials:

5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

lapatanib

Refernces

• 1、 Yamaguchi, Akitake,Kaldas, Sherif J.,Appavoo, Solomon D.,Diaz, Diego B.,Yudin, Andrei K.. "Conformationally stable peptide macrocycles assembled using the Petasis borono-Mannich reaction". supporting information. p. 10567 - 10570. Retrieved 2019/09/06.
• 2、 -. "A METHOD OF PRODUCING THE KEY INTERMEDIATE OF LAPATINIB SYNTHESIS". Page/Page column 7. . Retrieved 2014/05/07.