2-Isopropoxyphenylboronic acid

Base Information

• Chemical Name: 2-Isopropoxyphenylboronic acid
• CAS No.: 138008-97-6
• Molecular Formula: C9H13BO3
• Molecular Weight: 180.011
• Hs Code.: 2931900090
• European Community (EC) Number: 696-268-7
• DSSTox Substance ID: DTXSID80408161
• Nikkaji Number: J2.508.428D
• Wikidata: Q72485622
• Mol file: 138008-97-6.mol

Synonyms:2-Isopropoxyphenylboronic acid;138008-97-6;(2-Isopropoxyphenyl)boronic acid;(2-propan-2-yloxyphenyl)boronic Acid;C9H13BO3;MFCD03427050;2-Isopoxybenzeneboronic acid;Boronic acid, B-[2-(1-methylethoxy)phenyl]-;2-ISOPROPOXYBENZENEBORONIC ACID;Boronic acid, [2-(1-methylethoxy)phenyl]-;SCHEMBL522469;2-isopropoxylphenylboronic acid;(2-Isopropoxyphenyl)boronicacid;2-isopropoxyphenyl boronic acid;2-isopropyloxyphenylboronic acid;DTXSID80408161;XDMKBIIRBDPSOE-UHFFFAOYSA-N;AMY39588;BCP08469;AKOS004116516;AB15037;AC-6361;CS-W003075;FS-4314;SY023531;FT-0655931;A26766;J-509748

Chemical Property of 2-Isopropoxyphenylboronic acid

Chemical Property:

• Vapor Pressure: 5.98E-05mmHg at 25°C
• Melting Point: 30-35 °C(lit.)
• Refractive Index: n20/D >1.5090(lit.)
• Boiling Point: 199 °C
• PKA: 8.67±0.58(Predicted)
• Flash Point: 110 ºC
• PSA: 49.69000
• Density: 1.075 g/cm³
• LogP: 0.15360
• Storage Temp.: Keep Cold
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 180.0957744
• Heavy Atom Count: 13
• Complexity: 150

Purity/Quality:

99% ^*data from raw suppliers

2-Isopropoxyphenylboronic acid ^*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=C1OC(C)C)(O)O
• Uses: Reactant for:Suzuki arylationPalladium-catalyzed Suzuki-Miyaura reaction

Technology Process of 2-Isopropoxyphenylboronic acid

There total 4 articles about 2-Isopropoxyphenylboronic 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: 70.0%

1-bromo-2-isopropoxybenzene (701-07-5) → 2-isopropoxyphenylboronic acid (138008-97-6)

Guidance literature:

1-bromo-2-isopropoxybenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -90 ℃; for 0.25h;

With Trimethyl borate; In tetrahydrofuran; hexane; at -90 - 20 ℃; for 2h;

With hydrogenchloride; pH=5 - 6; cooling;

DOI:10.1016/S0040-4020(00)00928-5

Reference yield:

Trimethyl borate (121-43-7,63156-11-6) + 1-bromo-2-isopropoxybenzene (701-07-5) + water (7732-18-5) → 2-isopropoxyphenylboronic acid (138008-97-6)

Guidance literature:

1-bromo-2-isopropoxybenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 12h; Inert atmosphere;

water; With hydrogenchloride; In tetrahydrofuran; hexane; for 5h; Inert atmosphere;

DOI:10.1021/acs.orglett.1c01671

Reference yield:

phenol (108-95-2,27073-41-2) → 2-isopropoxyphenylboronic acid (138008-97-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-Bromosuccinimide / acetonitrile / 0.5 h / 0 - 20 °C

2.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

3.2: 12 h / -78 - 20 °C / Inert atmosphere

3.3: 5 h / Inert atmosphere

With N-Bromosuccinimide; n-butyllithium; potassium carbonate; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.orglett.1c01671

upstream raw materials:

1-bromo-2-isopropoxybenzene

Trimethyl borate

water

phenol

Downstream raw materials:

ethyl 4-iso-butyl-6-(2-isopropoxyphenyl)pyridazine-3-carboxylate

1-(2-isopropoxyphenyl)-6-methoxy-2-naphthaldehyde

6,7-dimethoxy-1-(2-isopropoxyphenyl)-2-naphthaldehyde

1-(2-isopropoxyphenyl)-2-naphthaldehyde

Refernces

• 1、 Chaumeil,Signorella,Le Drian. "Suzuki cross-coupling reaction of sterically hindered aryl boronates with 3-iodo-4-methoxybenzoic acid methylester". . p. 9655 - 9662. Retrieved 2007/10/03.