2-Formylfuran-5-boronic acid

Base Information

• Chemical Name: 2-Formylfuran-5-boronic acid
• CAS No.: 27329-70-0
• Molecular Formula: C5H5BO4
• Molecular Weight: 139.903
• Hs Code.: 29321900
• European Community (EC) Number: 628-001-7
• DSSTox Substance ID: DTXSID50370245
• Nikkaji Number: J1.512.068A
• Wikidata: Q72479252
• Mol file: 27329-70-0.mol

Synonyms:27329-70-0;2-Formylfuran-5-boronic acid;(5-formylfuran-2-yl)boronic acid;5-Formyl-2-furanboronic acid;5-formylfuran-2-boronic acid;5-formyl-2-furylboronic acid;5-formyl-2-furanylboronic acid;MFCD01114696;5-formylfuran-2-ylboronic acid;(5-formyl-2-furyl)boronic acid;Boronic acid, (5-formyl-2-furanyl)-;(5-formyl-2-furanyl)boronic acid;5-Borono-2-furaldehyde;SCHEMBL9221;5-Formylfuran-2-boronicacid;5-formyl-2 furylboronic acid;AI-372/25005759;5-Formyl-2-furan boronic acid;5-formyl-2-furan-boronic acid;5-formyl-2-furyl boronic acid;5-formyl-furan-2-boronic acid;2-Formyl-5-furanylboronic acid;(5-formylfuran-2-yl)boronicacid;(5-formylfuran-2yl)boronic acid;DTXSID50370245;(5-formylfuran-2Y1)boronic acid;JUWYQISLQJRRNT-UHFFFAOYSA-N;BCP22987;STL305009;TD8089;AKOS000320207;AC-6210;CS-W009133;GS-6784;Boronic acid, B-(5-formyl-2-furanyl)-;SY007281;A5315;AM20090813;F0611;FT-0620438;EN300-49190;J-517570;Q-101359;F1371-0203

Chemical Property of 2-Formylfuran-5-boronic acid

Chemical Property:

• Appearance/Colour: beige to brown powder
• Vapor Pressure: 1.98E-06mmHg at 25°C
• Melting Point: 136 °C (dec.)(lit.)
• Refractive Index: 1.51
• Boiling Point: 379.3 °C at 760 mmHg
• PKA: 7.11±0.53(Predicted)
• Flash Point: 183.2 °C
• PSA: 70.67000
• Density: 1.36 g/cm³
• LogP: -1.22810
• Storage Temp.: 0-6°C
• Sensitive.: Air Sensitive
• Solubility.: 1.38g/l
• Water Solubility.: Insoluble in water.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 140.0280888
• Heavy Atom Count: 10
• Complexity: 127

Purity/Quality:

98% ^*data from raw suppliers

5-Formylfuran-2-boronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, Xi
• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 26-36/37/39-45-37/39-27

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(O1)C=O)(O)O
• Uses: suzuki reaction As a bifunctional reagent used in the synthesis of π -extended heteroarylfuran systems. Reactant involved in Suzuki coupling for synthesis of stable dye-sensitized solar cells. Reactant involved in synthesis of biologically active molecules including, heteroarylation for the synthesis of HIF-1 inhibitors, disalicylic acid-furanyl derivatives to inhibit ephrin binding, HIV-1 integrase inhibitors, epidermal growth factor receptor inhibitors.

Technology Process of 2-Formylfuran-5-boronic acid

There total 6 articles about 2-Formylfuran-5-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: 81.5%

2-(diethoxymethyl)furan (13529-27-6) + Trimethyl borate (121-43-7,63156-11-6) → 5-formylfurane-2-boronic acid (27329-70-0)

Guidance literature:

2-(diethoxymethyl)furan; With biphenyl; para-chlorotoluene; lithium; In tetrahydrofuran; at -65 ℃; for 9h;

Trimethyl borate; In tetrahydrofuran; at -65 ℃; for 1h;

With hydrogenchloride; In tetrahydrofuran; water; pH=6.3;

Reference yield: 78.0%

5-bromo-2-furancarboxaldehyde (1899-24-7) + Triisopropyl borate (5419-55-6) → 5-formylfurane-2-boronic acid (27329-70-0)

Guidance literature:

5-bromo-2-furancarboxaldehyde; With n-butyllithium; In tetrahydrofuran; hexane; toluene; at -60 - -50 ℃; for 1.16667h;

Triisopropyl borate; In tetrahydrofuran; hexane; toluene;

DOI:10.1111/cbdd.12881

Reference yield: 75.0%

2-(diethoxymethyl)furan (13529-27-6) → 5-formylfurane-2-boronic acid (27329-70-0)

Guidance literature:

2-(diethoxymethyl)furan; With Triisopropyl borate; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; at -10 - 0 ℃; for 1h;

With hydrogenchloride; In tetrahydrofuran; n-heptane; ethylbenzene; water; at 30 ℃;

upstream raw materials:

2-(diethoxymethyl)furan

Trimethyl borate

2-(furan-2-yl)-1,3-dioxolane

5-bromo-2-furancarboxaldehyde

Downstream raw materials:

5-phenylfuran-2-carbaldehyde

5-[3-(trifluoromethyl)phenyl]furan-2-carbaldehyde

5-(4-hydroxyphenyl)-2-furancarboxaldehyde

5-(4-methoxyphenyl)furan-2-carbaldehyde

Refernces

• 1、 Ji, Sen,Ma, Shuang,Wang, Wen-Jing,Huang, Shen-Zhen,Wang, Tian-Qi,Xiang, Rong,Hu, Yi-Guo,Chen, Qiang,Li, Lin-Li,Yang, Sheng-Yong. "Discovery of selective protein arginine methyltransferase 5 inhibitors and biological evaluations". . p. 585 - 598. Retrieved 2017/04/06.
• 2、 -. "Method for the Production of Functionalized Five-Ring Heterocycles, and use thereof". Page/Page column 9. . Retrieved 2009/05/28.