5-Formylfuran-3-boronic acid

Base Information

• Chemical Name: 5-Formylfuran-3-boronic acid
• CAS No.: 62306-80-3
• Molecular Formula: C5H5BO4
• Molecular Weight: 139.90
• Hs Code.: 29349990
• European Community (EC) Number: 695-546-5
• DSSTox Substance ID: DTXSID80411039
• Wikidata: Q72479246
• Mol file: 62306-80-3.mol

Synonyms:5-Formylfuran-3-boronic acid;62306-80-3;(5-formylfuran-3-yl)boronic acid;2-Formylfuran-4-boronic acid;5-formylfuran-3-ylboronic acid;2-Formyl-4-furanboronic acid;2-Formyl-furan-4-boronic acid;MAY-GRUNWALDSEOSINMETHYLENEBLUE;2-formyl-4-furan boronic acid;5-Formyl furan-3-boronic acid;SCHEMBL1108282;(5-formylfuran-3-yl)boronicacid;DTXSID80411039;RIBSTTPRQPAXRS-UHFFFAOYSA-N;AMY19543;BCP12595;AKOS004116561;AB08818;Boronic acid, (5-formyl-3-furanyl)-;DS-12531;CS-0036469;FT-0647961;F20605;A833707;(5-formyl-3-furyl)boronic acid;(5-Formylfuran-3-yl)boronic acid

Chemical Property of 5-Formylfuran-3-boronic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.98E-06mmHg at 25°C
• Refractive Index: 1.51
• Boiling Point: 379.3 °C at 760 mmHg
• PKA: 7.25±0.10(Predicted)
• Flash Point: 183.2 °C
• PSA: 70.67000
• Density: 1.36 g/cm³
• LogP: -1.22810
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• 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%,99%, ^*data from raw suppliers

5-formylfuran-3-ylboronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=COC(=C1)C=O)(O)O

Technology Process of 5-Formylfuran-3-boronic acid

There total 7 articles about 5-Formylfuran-3-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: 91.0%

2-(diethoxymethyl)-4-bromofuran (27065-51-6) + Triisopropyl borate (5419-55-6) + water (7732-18-5) → (5-formylfuran-3-yl)boronic acid (62306-80-3)

Guidance literature:

2-(diethoxymethyl)-4-bromofuran; With n-butyllithium; In tetrahydrofuran; hexane; toluene; at -70 - -65 ℃; for 1.5h;

Triisopropyl borate; With 4-methyl-2-pentanone; at -40 ℃;

water; With perchloric acid; at 0 - 5 ℃; for 1.5h; pH=1 - 1.5;

Reference yield: 80.0%

4-iodofurfural diethyl acetal (915040-89-0) + Triisopropyl borate (5419-55-6) → (5-formylfuran-3-yl)boronic acid (62306-80-3)

Guidance literature:

4-iodofurfural diethyl acetal; Triisopropyl borate; With n-butyllithium; In tetrahydrofuran; hexane; toluene; at -70 - 20 ℃; for 1.5h;

With hydrogenchloride; water; at 0 - 20 ℃; for 1.5h; pH=0.8 - 1.5; Product distribution / selectivity;

Reference yield: 76.0%

2-(diethoxymethyl)-4-bromofuran (27065-51-6) + Triisopropyl borate (5419-55-6) → (5-formylfuran-3-yl)boronic acid (62306-80-3)

Guidance literature:

2-(diethoxymethyl)-4-bromofuran; Triisopropyl borate; With tri-n-butyllithium magnesate complex; In tetrahydrofuran; hexane; at -70 - 20 ℃;

With hydrogenchloride; water; at 0 - 20 ℃; for 1.5h; pH=0.8 - 1.5; Product distribution / selectivity;

upstream raw materials:

4-bromofurfural dimethyl acetal

Triisopropyl borate

4-bromo-2-furancarboxyaldehyde ethylene acetal

2-(diethoxymethyl)-4-bromofuran

Downstream raw materials:

(5-formylfuran-3-yl)(triphenyl-λ5-phosphanyl)gold

4-(5-formylfuran-2-yl)-2-(trifluoromethyl)benzonitrile

4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-(5-formylfuran-3-yl)-6-methoxyquinoline-3-carbonitrile

7-[(2, 4-dichloro-5-methoxyphenyl) amino]-2-(5-formyl-3-furyl) thieno [3,2-b] pyridine-6-carbonitrile

Refernces

• 1、 -. "METHOD FOR PRODUCING 2-FORMYLFURAN-4-BORONIC ACID BY THE METALATION OF 4-HALOFURFURAL ACETALS IN THE PRESENCE OF SUITABLE BORONIC ACID ESTERS OR ANHYDRIDES". Page/Page column 8. . Retrieved 2008/06/13.