4-(Methoxymethyl)phenylboronic acid

Base Information

• Chemical Name: 4-(Methoxymethyl)phenylboronic acid
• CAS No.: 279262-11-2
• Molecular Formula: C₈H₁₁BO₃
• Molecular Weight: 165.985
• Hs Code.: 2931900090
• European Community (EC) Number: 631-073-2
• DSSTox Substance ID: DTXSID30395552
• Nikkaji Number: J2.328.513D
• Wikidata: Q82195695
• Mol file: 279262-11-2.mol

Synonyms:279262-11-2;4-(Methoxymethyl)phenylboronic acid;(4-(Methoxymethyl)phenyl)boronic acid;4-Methoxymethylphenylboronic acid;4-Methoxymethylbenzeneboronic acid;[4-(methoxymethyl)phenyl]boronic Acid;4-(Methoxymethyl)benzeneboronic Acid;(4-(Methoxymethoxy)phenyl)boronic acid;4-(Methoxymethoxy)phenylboronic acid;SCHEMBL104085;DTXSID30395552;4-methoxymethyl-phenylboronic acid;4-methoxymethylphenyl boronic acid;VTNVZXAYRMTKON-UHFFFAOYSA-N;4-methoxymethyl-benzene boronic acid;MFCD03788426;6-Chloro-indan-1-ylaminehydrochloride;AKOS004116558;AB16006;AM86823;PS-9462;CS-0150194;FT-0676998;M2677;4-methoxymethylphenylboronic acid, AldrichCPR;D71358;I12121;EN300-1259725;A810401;A854224;Z823983404

Chemical Property of 4-(Methoxymethyl)phenylboronic acid

Chemical Property:

• Boiling Point: 296.2 °C at 760 mmHg
• PKA: 8.59±0.17(Predicted)
• Flash Point: 132.9 °C
• PSA: 49.69000
• Density: 1.13 g/cm³
• LogP: -0.48720
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: soluble in Methanol
• Water Solubility.: Slightly soluble in water.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 166.0801244
• Heavy Atom Count: 12
• Complexity: 122

Purity/Quality:

97% ^*data from raw suppliers

(4-(Methoxymethyl)phenyl)boronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)COC)(O)O
• Uses: 4-(Methoxymethyl)benzeneboronic acid is used as an organic chemical synthesis intermediate.

Technology Process of 4-(Methoxymethyl)phenylboronic acid

There total 3 articles about 4-(Methoxymethyl)phenylboronic 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: 85.7%

Trimethyl borate (121-43-7,63156-11-6) + 1-bromo-4-methoxymethylbenzene (1515-88-4) → (4-(methoxymethyl)phenyl)boronic acid (279262-11-2)

Guidance literature:

1-bromo-4-methoxymethylbenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -80 - -70 ℃; for 1h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; hexane; at -70 - -30 ℃; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; hexane; water; Inert atmosphere;

Reference yield: 36.0%

Triisopropyl borate (5419-55-6) + 1-bromo-4-methoxymethylbenzene (1515-88-4) → (4-(methoxymethyl)phenyl)boronic acid (279262-11-2)

Guidance literature:

1-bromo-4-methoxymethylbenzene; With n-butyllithium; In tetrahydrofuran; hexane; toluene; at -78 ℃; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; hexane; toluene; at -78 - -20 ℃; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; hexane; water; toluene; at -20 - 20 ℃; Inert atmosphere;

DOI:10.1021/jacs.8b03257

Reference yield:

1-bromomethyl-4-bromobenzene (589-15-1) → (4-(methoxymethyl)phenyl)boronic acid (279262-11-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere

1.2: Reflux; Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; toluene; hexane / -78 °C / Inert atmosphere

2.2: -78 - -20 °C / Inert atmosphere

2.3: -20 - 20 °C / Inert atmosphere

With n-butyllithium; sodium hydride; In tetrahydrofuran; hexane; toluene;

DOI:10.1021/jacs.8b03257

upstream raw materials:

1-bromomethyl-4-bromobenzene

Triisopropyl borate

1-bromo-4-methoxymethylbenzene

Trimethyl borate

Refernces

• 1、 Ogden, William A.,Guan, Zhibin. "Recyclable, Strong, and Highly Malleable Thermosets Based on Boroxine Networks". . p. 6217 - 6220. Retrieved 2018/05/23.