3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID

Base Information

• Chemical Name: 3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID
• CAS No.: 459423-32-6
• Molecular Formula: C17H23BO3
• Molecular Weight: 286.179
• Hs Code.: 2931900090
• Mol file: 459423-32-6.mol

Synonyms:Boronicacid, (4-methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)- (9CI);[3-(1-Adamantyl)-4-methoxyphenyl]boronic acid;{3-[(3s,5s,7s)-Adamantan-1-yl]-4-methoxyphenyl}boronic acid;Boronic acid, B-(4-methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-;

Chemical Property of 3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID

Chemical Property:

• Vapor Pressure: 7.89E-10mmHg at 25°C
• Melting Point: 239-242
• Refractive Index: 1.583
• Boiling Point: 475.008 °C at 760 mmHg
• PKA: 8.94±0.10(Predicted)
• Flash Point: 241.076 °C
• PSA: 49.69000
• Density: 1.2 g/cm³
• LogP: 1.84280
• Storage Temp.: Keep Cold

Purity/Quality:

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

3-(1-Adamantyl)-4-methoxyphenylboronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Promotes the ortho hydroxalkylation of phenols by aldehyde. Used as reagent in the proection of thiols as cyclic boronates. This has been utilized to trap cis thiols in oder to prevent over oxidation during dihydroxylation reaction by osmium (4)oxide.

Technology Process of 3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID

There total 5 articles about 3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC 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: 94.8%

Triisopropyl borate (5419-55-6) → 3-(1-adamantyl)-4-methoxyphenylboronic acid (459423-32-6)

Guidance literature:

2-(1-adamantyl)-4-bromoanisole; With n-butyllithium; In tetrahydrofuran; at -75 - -70 ℃; for 1h;

Triisopropyl borate; In tetrahydrofuran; at -70 - 20 ℃;

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

Reference yield: 72.0%

Trimethyl borate (121-43-7,63156-11-6) + 2-(1-adamantyl)-4-bromoanisole (104224-63-7) → 3-(1-adamantyl)-4-methoxyphenylboronic acid (459423-32-6)

Guidance literature:

With magnesium; 1,2-dibromoethane; lithium chloride; In tetrahydrofuran; under Ar; Mg and LiCl in THF heated at 40°C, 1,2-Br2C2H4 added, 2-(1-adamantyl)-4-Br-anisole in THF added at slight boiling temp., boiling for 0.5 h, decantation, soln. added to soln. of B(OMe)3 in THF at 0-5°C, stored at 0°C (16 h); HCl and water added, mixt. extd. with Et2O, org. phase dried over Na2SO4, evapn. under vac., residue treated with EtOAc, soln. stored at 0°C overnight, ppt. filtered off, washed with cold EtOAc, dried at 100°C;

DOI:10.1134/S1070363210040316

Reference yield: 12.0%

2-(1-adamantyl)-4-bromoanisole (104224-63-7) → 3-(1-adamantyl)-4-methoxyphenylboronic acid (459423-32-6)

Guidance literature:

2-(1-adamantyl)-4-bromoanisole; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.0833333h;

With triethyl borate; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

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

upstream raw materials:

2-(1-adamantyl)-4-bromoanisole

Triisopropyl borate

Trimethyl borate

Downstream raw materials:

6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

2-(3-adamantan-1-yl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

adapalene

Refernces

• 1、 Tribulovich,Garabadzhiu,Kalvins. "Synthesis of 3-(1-adamantyl)-4-methoxyphenylboric acid". . p. 868 - 869. Retrieved 2011/01/10.
• 2、 -. "NOVEL THERAPEUTIC AGENTS FOR THE TREATMENT OF CANCER, METABOLIC DISEASES AND SKIN DISORDERS". Page/Page column 51. . Retrieved 2008/06/13.