2-Formyl-4-methoxyphenylboronic acid

Base Information

• Chemical Name: 2-Formyl-4-methoxyphenylboronic acid
• CAS No.: 139962-95-1
• Molecular Formula: C8H9BO4
• Molecular Weight: 179.968
• Hs Code.: 2931900090
• European Community (EC) Number: 672-300-5
• DSSTox Substance ID: DTXSID00370255
• Nikkaji Number: J1.445.659G
• Wikidata: Q72489924
• Mol file: 139962-95-1.mol

Synonyms:2-Formyl-4-methoxyphenylboronic acid;139962-95-1;4-Methoxy-2-formylphenylboronic acid;(2-formyl-4-methoxyphenyl)boronic acid;2-FORMYL-4-METHOXYBENZENEBORONIC ACID;MFCD01319043;2-formyl-4-methoxyphenylboronicacid;2-BORONO-5-METHOXYBENZALDEHYDE;SCHEMBL50949;DTXSID00370255;ZSSNGMFKYFBOAG-UHFFFAOYSA-N;AKOS004116320;AB08871;AM86585;PS-9480;SY033602;2-Formyl-4-methoxyphenylboronic acid, 97%;CS-0100651;F1108;FT-0612457;Boronic acid, B-(2-formyl-4-methoxyphenyl)-;I12185;EN300-7383696;A807604;J-509536

Chemical Property of 2-Formyl-4-methoxyphenylboronic acid

Chemical Property:

• Appearance/Colour: white to light yellow powder
• Vapor Pressure: 5.89E-07mmHg at 25°C
• Melting Point: 148 °C
• Refractive Index: 1.537
• Boiling Point: 395.238 °C at 760 mmHg
• PKA: 8.61±0.53(Predicted)
• Flash Point: 192.833 °C
• PSA: 66.76000
• Density: 1.26 g/cm³
• LogP: -0.81250
• Storage Temp.: 0-6°C
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 180.0593889
• Heavy Atom Count: 13
• Complexity: 174

Purity/Quality:

98% ^*data from raw suppliers

2-Formyl-4-methoxyphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(C=C(C=C1)OC)C=O)(O)O
• Uses: suzuki reaction

Technology Process of 2-Formyl-4-methoxyphenylboronic acid

There total 13 articles about 2-Formyl-4-methoxyphenylboronic 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: 92.7%

2-Bromo-5-methoxybenzaldehyde ethylene glycol acetal (98015-07-7) → 2-formyl-4-methoxyphenylboronic acid (139962-95-1)

Guidance literature:

2-Bromo-5-methoxybenzaldehyde ethylene glycol acetal; With n-butyllithium; In diethyl ether; hexane; at -75 ℃; for 1h;

With Triisopropyl borate; In diethyl ether; hexane; at 20 ℃; for 2.5h;

With hydrogenchloride; In diethyl ether; hexane; for 1.5h; Further stages.; Heating;

DOI:10.1039/b100345n

Reference yield: 92.7%

Triisopropyl borate (5419-55-6) + 2-Bromo-5-methoxybenzaldehyde ethylene glycol acetal (98015-07-7) → 2-formyl-4-methoxyphenylboronic acid (139962-95-1)

Guidance literature:

With hydrogenchloride; n-butyllithium; In diethyl ether; hexane; (N2); addn. of a soln. of BuLi in hexane to a soln. of acetal in ether at -75°C, stirring for 1 h, addn. of boron compd., stirring at room temp. for 2.5 h, addn. of aq. HCl, refluxing for 1.5 h with stirring; sepn. of ppt., extn. with aq. NaOH, acidification of the ext.;

DOI:10.1039/b100345n

Reference yield: 52.0%

2-(2-bromo-5-methoxyphenyl)-1,3-dioxane (1186304-21-1) → 2-formyl-4-methoxyphenylboronic acid (139962-95-1)

Guidance literature:

2-(2-bromo-5-methoxyphenyl)-1,3-dioxane; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

With Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃;

With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃;

DOI:10.1002/ejoc.201001023

upstream raw materials:

2-Bromo-5-methoxybenzaldehyde ethylene glycol acetal

2-bromo-5-methoxy-benzaldehyde

3-methoxy-benzaldehyde

Triisopropyl borate

Downstream raw materials:

3-(2-Formyl-4-methoxyphenyl)dibenzo[b,d]thiophene

5-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

1-(2-methoxyphenanthren-9-yl)ethanone

C₂₈H₃₃NO₆

Refernces

• 1、 Chen, Fener,Chen, Xiao-Pan,Deng, Ji,Li, Gen,Li, Guo-Bo,Schofield, Christopher J.,Xiao, You-Cai,Yan, Yu-Hang,Yu, Jun-Lin,Zhu, Kai-Rong,Brem, Jürgen. "Design and enantioselective synthesis of 3-(α-acrylic acid) benzoxaboroles to combat carbapenemase resistance". . p. 7709 - 7712. Retrieved 2021/08/09.
• 2、 Bien, Jeffrey,Davulcu, Akin,Delmonte, Albert J.,Fraunhoffer, Kenneth J.,Gao, Zhinong,Hang, Chao,Hsiao, Yi,Hu, Wenhao,Katipally, Kishta,Littke, Adam,Pedro, Aghogho,Qiu, Yuping,Sandoval, Maria,Schild, Richard,Soltani, Michelle,Tedesco, Anthony,Vanyo, Dale,Vemishetti, Purushotham,Waltermire, Robert E.. "The First Kilogram Synthesis of Beclabuvir, an HCV NS5B Polymerase Inhibitor". . p. 1393 - 1408. Retrieved 2018/09/06.