2-Formylphenylboronic acid

Base Information

• Chemical Name: 2-Formylphenylboronic acid
• CAS No.: 40138-16-7
• Molecular Formula: C7H7BO3
• Molecular Weight: 149.942
• Hs Code.: 2931900090
• European Community (EC) Number: 628-526-1
• NSC Number: 157839
• UNII: MT69HY4FNF
• DSSTox Substance ID: DTXSID30901733
• Nikkaji Number: J1.082.419B
• Wikidata: Q106902657
• ChEMBL ID: CHEMBL139725
• Mol file: 40138-16-7.mol

Synonyms:2-formylphenylboronic acid;o-formylphenylboronic acid

Chemical Property of 2-Formylphenylboronic acid

Chemical Property:

• Appearance/Colour: light yellow to tan powder
• Vapor Pressure: 1.12E-05mmHg at 25°C
• Melting Point: 115-120 °C(lit.)
• Refractive Index: 1.547
• Boiling Point: 355.7 °C at 760 mmHg
• PKA: 8.18±0.53(Predicted)
• Flash Point: 169 °C
• PSA: 57.53000
• Density: 1.24 g/cm³
• LogP: -0.82110
• Storage Temp.: 0-6°C
• Sensitive.: Air Sensitive
• Solubility.: Soluble in methanol.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 150.0488242
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

2-Formylphenylboronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=CC=C1C=O)(O)O
• Uses: suzuki reaction 2-Formylbenzeneboronic acid is used as an organic chemical synthesis intermediate.

Technology Process of 2-Formylphenylboronic acid

There total 27 articles about 2-Formylphenylboronic 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: 100.0%

2-(2'-formylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (380151-85-9) → 2-formylbenzene boronic acid (40138-16-7)

Guidance literature:

2-(2'-formylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; With potassium hydrogen difluoride; In methanol; at 20 ℃; for 0.25h;

With lithium hydroxide; In acetonitrile; at 20 ℃; for 20h;

DOI:10.1016/j.tetlet.2005.09.101

Reference yield: 83.0%

2-chlorobenzaldehyde diethyl acetal (35364-86-4) → 2-formylbenzene boronic acid (40138-16-7)

Guidance literature:

Reference yield: 68.0%

2-(2-bromophenyl)-1,3-dioxolan (34824-58-3) + Trimethyl borate (121-43-7,63156-11-6) → 2-formylbenzene boronic acid (40138-16-7)

Guidance literature:

With Mg and MeMgBr; aq. HCl; aq. NaOH; In tetrahydrofuran; (Ar); stirring dioxolane with Mg and MeMgBr (room temp., 30 min), heating at reflux (4 h), cooling (0°C), adding precooled (-78°C)B(OMe)3, stirring (4 h), warming (room temp., overnight), treating with aq. HCl; layers sepn., extn. of aq. layer (ether), extn. of ether ext. (aq. NaOH), acidification (aq. HCl, pH=3), extn. (ether), drying (MgSO4), evapn.;

DOI:10.1021/ja963784i

upstream raw materials:

(2-Br₂CHC₆H₄)B(OH)2

2-(2'-formylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-Methylphenylboronic acid

2-chlorobenzaldehyde diethyl acetal

Downstream raw materials:

2,9-bis-1,10-phenanthroline

2-(2-thienyl)benzaldehyde

2-(thien-3-yl)benzaldehyde

2-(pyridin-3-yl)benzaldehyde

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". supporting information. p. 7709 - 7712. Retrieved 2021/08/09.
• 2、 Singh, Akansha,Kumar, Ravindra. "Sustainable Passerini-tetrazole three component reaction (PT-3CR): selective synthesis of oxaborol-tetrazoles". . p. 9708 - 9711. Retrieved 2021/09/30.