5-Chloro-2-formylphenylboronic acid

Base Information

• Chemical Name: 5-Chloro-2-formylphenylboronic acid
• CAS No.: 870238-36-1
• Molecular Formula: C₇H₆BClO₃
• Molecular Weight: 184.387
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID30396701
• Wikidata: Q72451617
• Mol file: 870238-36-1.mol

Synonyms:5-Chloro-2-formylphenylboronic acid;870238-36-1;(5-chloro-2-formylphenyl)boronic acid;MFCD03425955;5-Choloro-2-Formylphenyl Boronic Acid;5-Chloro-2-formylphenylboronicacid;Boronic acid, (5-chloro-2-formylphenyl)-;SCHEMBL380410;DTXSID30396701;LVNPJTSTUBPCMK-UHFFFAOYSA-N;BBL103945;STL557755;5-Choloro-2-Formylphenylboronic Acid;AKOS004114069;AB14723;AM90142;CS-W016992;DS-12720;SY026621;FT-0685296;Y10143;5-Chloro-2-formylphenylboronic acid, AldrichCPR;EN300-7370074;A841918;J-517306;(5-chloro-2-formyl-phenyl)boronic acid;5-Chloro-2-formylphenylboronic Acid

Chemical Property of 5-Chloro-2-formylphenylboronic acid

Chemical Property:

• Vapor Pressure: 6.58E-07mmHg at 25°C
• Boiling Point: 393.8 ºC at 760 mmHg
• PKA: 7.21±0.53(Predicted)
• Flash Point: 192ºC
• PSA: 57.53000
• Density: 1.4 g/cm³
• LogP: -0.16770
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 184.0098519
• Heavy Atom Count: 12
• Complexity: 165

Purity/Quality:

99% ^*data from raw suppliers

5-Chloro-2-formylphenylboronic acid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 5-Chloro-2-formylphenylboronic acid

There total 4 articles about 5-Chloro-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:

4-chloro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzaldehyde (1246633-36-2) → (2-formyl-5-chlorophenyl)boronic acid (870238-36-1)

Guidance literature:

4-chloro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzaldehyde; With sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 0.333333h;

With hydrogenchloride; In tetrahydrofuran; water; for 2h;

DOI:10.1016/j.bmcl.2021.127956

Reference yield:

2-bromo-4-chloro-1-(diethoxymethyl)benzene (198967-22-5) + Triisopropyl borate (5419-55-6) → (2-formyl-5-chlorophenyl)boronic acid (870238-36-1)

Guidance literature:

2-bromo-4-chloro-1-(diethoxymethyl)benzene; With n-butyllithium; In tetrahydrofuran; at -78 - -40 ℃; for 0.25h;

Triisopropyl borate; In tetrahydrofuran; at 0 ℃;

Reference yield:

2-bromo-4-chlorobenzaldehyde (84459-33-6) → (2-formyl-5-chlorophenyl)boronic acid (870238-36-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sulfuric acid / ethanol / 1 h / Reflux

2.1: n-butyllithium / tetrahydrofuran / 0.25 h / -78 - -40 °C

2.2: 0 °C

With n-butyllithium; sulfuric acid; In tetrahydrofuran; ethanol;

upstream raw materials:

2-bromo-4-chloro-1-(diethoxymethyl)benzene

Triisopropyl borate

2-bromo-4-chlorobenzaldehyde

4-chloro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzaldehyde

Downstream raw materials:

C₂₉H₂₀ClO₂P

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、 -. "BORON CONTAINING COMPOUNDS AND THEIR USES". Paragraph 0205; 0207. . Retrieved 2021/01/23.