(4-(Acetoxymethyl)phenyl)boronic acid

Base Information

• Chemical Name: (4-(Acetoxymethyl)phenyl)boronic acid
• CAS No.: 326496-51-9
• Molecular Formula: C9H11 B O4
• Molecular Weight: 193.995
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID30442055
• Wikidata: Q82259120
• Mol file: 326496-51-9.mol

Synonyms:326496-51-9;(4-(Acetoxymethyl)phenyl)boronic acid;(4-Acetoxymethyl)phenylboronic acid;[4-(acetyloxymethyl)phenyl]boronic Acid;4-(Acetoxymethyl)benzeneboronic acid;{4-[(Acetyloxy)methyl]phenyl}boronic acid;MFCD08235082;[4-(Acetoxymethyl)phenyl]boronic acid;4-Acetoxymethylbenzeneboronic acid;(4-(Acetoxymethyl)phenyl)boronicacid;4-(ACETOXYMETHYL)BENZENEBORONIC ACID 97;SCHEMBL2494202;DTXSID30442055;AKOS006346242;BS-28031;CS-0173783;F74125;J-018818;(2-OXO-PYRROLIDIN-3-YL)-CARBAMICACIDBENZYLESTER

Chemical Property of (4-(Acetoxymethyl)phenyl)boronic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 81-83
• Boiling Point: 341°Cat760mmHg
• Flash Point: 160°C
• PSA: 66.76000
• Density: 1.21g/cm³
• LogP: -0.57050
• Storage Temp.: Keep Cold
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 194.0750390
• Heavy Atom Count: 14
• Complexity: 187

Purity/Quality:

97% ^*data from raw suppliers

(4-Acetoxymethyl)phenylboronicacid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (4-(Acetoxymethyl)phenyl)boronic acid

There total 4 articles about (4-(Acetoxymethyl)phenyl)boronic 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:

p-hydroxymethylphenylboronic acid (59016-93-2) + acetic anhydride (108-24-7) → (4-(acetoxymethyl)phenyl)boronic acid (326496-51-9)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1002/1099-0690(200012)2000:23<3825::aid-ejoc3825>3.3.co;2-7

Reference yield:

2-((4-bromobenzyl)oxy)tetrahydro-2H-pyran (17100-68-4) → (4-(acetoxymethyl)phenyl)boronic acid (326496-51-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 8.68 g / nBuLi; B(O-iPr)3 / tetrahydrofuran; hexane

2: p-TsOH*H₂O / ethanol / 4 h / 20 °C

3: 6.09 g / pyridine / 20 °C

With pyridine; n-butyllithium; Triisopropyl borate; toluene-4-sulfonic acid; In tetrahydrofuran; ethanol; hexane;

DOI:10.1002/1099-0690(200012)2000:23<3825::aid-ejoc3825>3.3.co;2-7

Reference yield:

4-bromobenzenemethanol (873-75-6) → (4-(acetoxymethyl)phenyl)boronic acid (326496-51-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / p-TsOH*H₂O / CH₂Cl₂ / 2 h / 20 °C

2: 8.68 g / nBuLi; B(O-iPr)3 / tetrahydrofuran; hexane

3: p-TsOH*H₂O / ethanol / 4 h / 20 °C

4: 6.09 g / pyridine / 20 °C

With pyridine; n-butyllithium; Triisopropyl borate; toluene-4-sulfonic acid; In tetrahydrofuran; ethanol; hexane; dichloromethane;

DOI:10.1002/1099-0690(200012)2000:23<3825::aid-ejoc3825>3.3.co;2-7

upstream raw materials:

p-hydroxymethylphenylboronic acid

acetic anhydride

2-((4-bromobenzyl)oxy)tetrahydro-2H-pyran

4-bromobenzenemethanol

Downstream raw materials:

4-(pyridin-2-yl)benzyl acetate

3-[(tert-butoxycarbonyl)amino]-4-(pyridin-2-yl)benzyl acetate

2-[(4-acetoxymethyl)phenyl]-4,5-dimethyl-1,3,2-dioxaborolane