4-(Hydroxymethyl)phenylboronic acid

Base Information

• Chemical Name: 4-(Hydroxymethyl)phenylboronic acid
• CAS No.: 59016-93-2
• Molecular Formula: C7H9BO3
• Molecular Weight: 151.958
• Hs Code.: 29319090
• European Community (EC) Number: 672-927-4
• DSSTox Substance ID: DTXSID20370454
• Nikkaji Number: J1.526.601E
• Wikidata: Q72485464
• Mol file: 59016-93-2.mol

Synonyms:59016-93-2;4-(Hydroxymethyl)phenylboronic acid;4-(Hydroxymethyl)benzeneboronic Acid;[4-(hydroxymethyl)phenyl]boronic Acid;4-hydroxymethylphenylboronic acid;(4-(hydroxymethyl)phenyl)boronic acid;(4-hydroxymethylphenyl)boronic acid;MFCD00792672;BORONIC ACID, [4-(HYDROXYMETHYL)PHENYL]-;4-hydroxymethyl phenylboronic acid;4-Hydroxymethyl phenyl boronic acid;SCHEMBL112402;4-hydroxymethylbenzeneboronic acid;DTXSID20370454;4(hydroxymethyl)phenylboronic acid;4-hydroxymethyl-phenylboronic acid;4-hydroxymethylphenyl boronic acid;PZRPBPMLSSNFOM-UHFFFAOYSA-N;4-(Hydroxymethyl)benzeneboronicAcid;4-hydroxymethylbenzene boronic acid;4-hydroxymethyl-phenyl-boronic acid;4-hydroxymethyl benzene boronic acid;4-(hydroxy methyl)phenylboronic acid;4-(hydroxymethyl) phenylboronic acid;4-(hydroxymethyl)-phenylboronic acid;4-(hydroxymethyl)phenyl boronic acid;4-(hydroxymethyl)phenyl-boronic acid;BBL102140;STL555939;4-(hydroxymethyl)benzene boronic acid;AKOS004116393;AB07121;AC-2440;AS-2467;CS-W000949;[4-(hydroxymethyl)phenyl] boronic acid;[4-(hydroxymethyl)-phenyl]-boronic acid;4-(hydroxy-methyl)-benzene boronic acid;SY001158;A8316;AM20060341;FT-0616785;H1204;EN300-175993;J-513749;Z1203162320;1-PYRROLIDIN-3-(2-CHLOROPHENYL)-3-(N-CBZ-N-METHYL)AMINO-PROPANE

Chemical Property of 4-(Hydroxymethyl)phenylboronic acid

Chemical Property:

• Appearance/Colour: Off-white Crystal
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 251-256 °C(lit.)
• Refractive Index: 1.567
• Boiling Point: 362.021 °C at 760 mmHg
• PKA: 8.53±0.10(Predicted)
• Flash Point: 172.744 °C
• PSA: 60.69000
• Density: 1.258 g/cm³
• LogP: -1.14130
• Storage Temp.: Refrigerator (+4°C)
• Water Solubility.: 25 g/L
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 152.0644743
• Heavy Atom Count: 11
• Complexity: 110

Purity/Quality:

99% ^*data from raw suppliers

4-(Hydroxymethyl)phenylboronic Acid (contains varying amounts of Anhydride) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)CO)(O)O
• Uses: suzuki reaction Reactant involved in the synthesis of biologically active compounds including:Imidazo[4,5-b]pyrazin-2-ones for use as mTOR kinase inhibitorsHuman immunodificiency virus protease inhibitors with activity against resistant virusesReactant involved in:Suzuki coupling reactionsCopper-catalyzed transformation from arylboronic acids in waterInvolved in the synthesis of polyurethane containing spindle-type chromophores

Technology Process of 4-(Hydroxymethyl)phenylboronic acid

There total 15 articles about 4-(Hydroxymethyl)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: 85.0%

4-(hydroxymethyl)phenylboronic acid MIDA ester (1072960-82-7) → p-hydroxymethylphenylboronic acid (59016-93-2)

Guidance literature:

With sodium hydroxide; water; In tetrahydrofuran; at 23 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1021/ja8063759

Reference yield: 85.0%

triethyl borate (150-46-9) + water (7732-18-5) + (4-bromo-benzyloxy)-dimethyl-phenyl-silane → p-hydroxymethylphenylboronic acid (59016-93-2)

Guidance literature:

(4-bromo-benzyloxy)-dimethyl-phenyl-silane; With magnesium; at 50 ℃; for 0.5h; Inert atmosphere;

triethyl borate; at -70 - -10 ℃; for 2.5h;

water; With 1-n-butyl-3-methylimidazolim bromide; at 20 - 30 ℃; for 0.5h;

Reference yield: 83.7%

Triisopropyl borate (5419-55-6) + water (7732-18-5) + 4-bromo((triethylsilyloxy)methyl)benzene → p-hydroxymethylphenylboronic acid (59016-93-2)

Guidance literature:

4-bromo((triethylsilyloxy)methyl)benzene; With magnesium; at 80 ℃; for 0.5h; Inert atmosphere;

Triisopropyl borate; at -30 - -10 ℃; for 2.66667h;

water; With 1-butyl-3-methylimidazolium hydrogen sulfate; at 0 - 30 ℃;

upstream raw materials:

<4-<<(tetrahydro-2H-pyran-2-yl)oxy>methyl>phenyl>boronic acid

4-bromobenzenemethanol

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

4-formylphenylboronic acid,

Downstream raw materials:

(4-(acetoxymethyl)phenyl)boronic acid

4-[[(4,4'-dimethoxytrityl)oxy]methyl]phenylboronic acid

6-[4-(hydroxymethyl)phenyl]-2-naphthol

4-(hydroxymethyl)phenylboronic acid MIDA ester

Refernces

• 1、 Zhang, Xiaoting,Wang, Shujuan,Jiang, Zikang,Li, Yu,Jing, Xinli. "Boronic Ester Based Vitrimers with Enhanced Stability via Internal Boron-Nitrogen Coordination". supporting information. p. 21852 - 21860. Retrieved 2021/01/11.
• 2、 Pratihar, Sanjay. "Electrophilicity and nucleophilicity of commonly used aldehydes". . p. 5781 - 5788. Retrieved 2014/07/22.