Tavaborole

Base Information

• Chemical Name: Tavaborole
• CAS No.: 174671-46-6
• Molecular Formula: C7H6BFO2
• Molecular Weight: 151.933
• Hs Code.: 2934999090
• European Community (EC) Number: 690-763-1
• UNII: K124A4EUQ3
• ChEMBL ID: CHEMBL443052
• DSSTox Substance ID: DTXSID00169888
• Metabolomics Workbench ID: 152105
• NCI Thesaurus Code: C81725
• Nikkaji Number: J2.495.581H
• Pharos Ligand ID: P2PR7P4UT6XC
• RXCUI: 1543173
• Wikidata: Q21011226
• Wikipedia: Tavaborole
• Mol file: 174671-46-6.mol

Synonyms:5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole;AN 2690;AN-2690;AN2690;Kerydin;tavaborole

Chemical Property of Tavaborole

Chemical Property:

• Melting Point: 120-122℃
• Boiling Point: 230.831 °C at 760 mmHg
• PKA: 6.81±0.20(Predicted)
• Flash Point: 93.404 °C
• PSA: 29.46000
• Density: 1.288 g/cm³
• LogP: 0.04340
• Storage Temp.: -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 152.0444878
• Heavy Atom Count: 11
• Complexity: 155

Purity/Quality:

97% ^*data from raw suppliers

Tavaborole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(C2=C(CO1)C=C(C=C2)F)O
• Recent ClinicalTrials: Cumulative Irritation Test
• Description: Tavaborole (Kerydin?), discovered and developed by Anacor, was approved by the US FDA in July 2014. Tavaborole, topical solution, 5% is an oxaborole antifungal indicated for the treatment of onychomycosis of the toenails due to Trichophyton rubrum or Trichophyton mentagrophytes. The mechanism of action of tavaborole is inhibition of fungal protein synthesis, which inhibits an aminoacyl-transfer ribonucleic acid synthetase.
• Uses: Tavaborole is a topical treatment of toenail onychomycosis.

Technology Process of Tavaborole

There total 27 articles about Tavaborole 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: 91.0%

5-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (943310-52-9) + water (7732-18-5) → tavaborole (174671-46-6)

Guidance literature:

5-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde; With methanol; sodium tetrahydroborate; at 20 ℃; for 1h; Industrial scale;

water; With hydrogenchloride; at 20 ℃; for 1h; pH=2; Reagent/catalyst; Industrial scale;

Reference yield: 81.0%

(4-fluoro-2-(hydroxymethyl)phenyl)boronic acid (1061223-45-7) → tavaborole (174671-46-6)

Guidance literature:

With sulfuric acid; at 20 ℃; for 4h;

Reference yield: 80.0%

5-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate → tavaborole (174671-46-6)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 4h; Reagent/catalyst; Temperature; Time;

upstream raw materials:

2-((methoxymethoxy)methyl)-4-fluorophenylboronic acid

3-fluoro-benzenemethanol

Triisopropyl borate

2-bromo-5-fluorobenzyl alcohol

Downstream raw materials:

1,1′-(propane-1,2-diylbis(oxy))bis(5-fluoro-1,3-dihydrobenzo[c][1,2]oxaborole)

1,1′-((2,3-dimethylbutane-2,3-diyl)bis(oxy))bis(5-fluoro-1,3-dihydrobenzo[c][1,2]oxaborole)