3-Borono-5-bromobenzoic acid

Base Information

• Chemical Name: 3-Borono-5-bromobenzoic acid
• CAS No.: 913835-73-1
• Molecular Formula: C7H6BBrO4
• Molecular Weight: 244.84
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID10466951
• Nikkaji Number: J2.607.550E
• Wikidata: Q82293633
• Mol file: 913835-73-1.mol

Synonyms:913835-73-1;3-Bromo-5-carboxyphenylboronic acid;3-Borono-5-bromobenzoic acid;3-Bromo-5-carboxybenzeneboronic acid;MFCD08689487;3-borono-5-bromo-benzoic Acid;3-Borono-5-bromobenzoicacid;3-BROMO-5-CARBOXYBENZENEBORONIC ACID 97;DTXSID10466951;AKOS015834289;AB48251;BP-10620;BS-29665;SY109977;5-BROMO-3-CARBOXYPHENYLBORONIC ACID;CS-0175141;FT-0687824;5-Bromo-3-carboxyphenylboronic acid, >=95%;D71454;A860498

Chemical Property of 3-Borono-5-bromobenzoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 290-292 °C
• Refractive Index: 1.641
• Boiling Point: 480.728 °C at 760 mmHg
• PKA: 3.82±0.10(Predicted)
• Flash Point: 244.536 °C
• PSA: 77.76000
• Density: 1.869 g/cm³
• LogP: -0.17290
• Storage Temp.: Keep Cold
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 243.95425
• Heavy Atom Count: 13
• Complexity: 199

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Bromo-5-carboxyphenylboronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CC(=C1)Br)C(=O)O)(O)O

Technology Process of 3-Borono-5-bromobenzoic acid

There total 1 articles about 3-Borono-5-bromobenzoic 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: 82.0%

1,3,5-trisbromobenzene (626-39-1) + carbon dioxide (124-38-9,18923-20-1) → 3-bromo-5-carboxyphenylboronic acid (913835-73-1)

Guidance literature:

1,3,5-trisbromobenzene; With n-butyllithium; In diethyl ether; hexane; at -80 ℃; for 0.5h; Inert atmosphere;

With Triisopropyl borate; In tetrahydrofuran; diethyl ether; hexane; at -70 ℃; for 0.5h; Inert atmosphere;

carbon dioxide; Further stages;

DOI:10.1002/ejoc.200800245

Reference yield:

3-bromo-5-carboxyphenylboronic acid (913835-73-1) → (2S,3R)-tert-butyl 3-(3-bromo-5-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidine-1-carboxylate

Guidance literature:

Multi-step reaction with 5 steps

1: sulfuric acid / 20 h / Reflux

2: diethyl ether / 1.5 h / 20 °C

3: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C

4: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C

5: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; lithium aluminium tetrahydride; chloro(1,5-cyclooctadiene)rhodium(I) dimer; sulfuric acid; water; caesium carbonate; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/acschemneuro.0c00003

Reference yield:

3-bromo-5-carboxyphenylboronic acid (913835-73-1) → (2S,3R)-tert-butyl 3-(3-bromo-5-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidine-1-carboxylate

Guidance literature:

Multi-step reaction with 6 steps

1: sulfuric acid / 20 h / Reflux

2: diethyl ether / 1.5 h / 20 °C

3: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C

4: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C

5: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

6: boron trichloride methyl sulfide complex / tetrahydrofuran / 2 h / Reflux

With 1H-imidazole; dmap; lithium aluminium tetrahydride; chloro(1,5-cyclooctadiene)rhodium(I) dimer; boron trichloride methyl sulfide complex; sulfuric acid; water; caesium carbonate; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/acschemneuro.0c00003

upstream raw materials:

1,3,5-trisbromobenzene

carbon dioxide

Downstream raw materials:

methyl 3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Refernces