Boronic acid, B-[4-[[4-[(Z)-[3-[(4-fluorophenyl)Methyl]-2,4-dioxo-5-thiazolidinylidene]Methyl]phenoxy]Methyl]phenyl]-

Base Information

• Chemical Name: Boronic acid, B-[4-[[4-[(Z)-[3-[(4-fluorophenyl)Methyl]-2,4-dioxo-5-thiazolidinylidene]Methyl]phenoxy]Methyl]phenyl]-
• CAS No.: 1312201-00-5
• Molecular Formula: C₂₄H₁₉BFNO₅S
• Molecular Weight: 463.294
• Mol file: 1312201-00-5.mol

Synonyms:Boronic acid, B-[4-[[4-[(Z)-[3-[(4-fluorophenyl)Methyl]-2,4-dioxo-5-thiazolidinylidene]Methyl]phenoxy]Methyl]phenyl]-;(Z)-4-((4-((3-(4-Fluorobenzyl)-2,4-dioxo-1,3-thiazolan-5-yliden)-methyl)phenoxy)methyl)benzeneboronic acid;B-[4-[[4-[(Z)-[3-[(4-Fluorophenyl)methyl]-2,4-dioxo-5-thiazolidinylidene]methyl]phenoxy]methyl]phenyl]-boronic acid;HA 155;HA155;(Z)-4-((4-((3-(4-fluorobenzyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)methyl)phenylboronic acid

Chemical Property of Boronic acid, B-[4-[[4-[(Z)-[3-[(4-fluorophenyl)Methyl]-2,4-dioxo-5-thiazolidinylidene]Methyl]phenoxy]Methyl]phenyl]-

Chemical Property:

• PSA: 112.37000
• LogP: 3.25890
• Storage Temp.: ?20°C
• Solubility.: DMSO: soluble10mg/mL, clear

Purity/Quality:

99% ^*data from raw suppliers

HA155 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: HA155 is a boronic acid based inhibitor of Autotaxins, such as ATX, NPP2.

Technology Process of Boronic acid, B-[4-[[4-[(Z)-[3-[(4-fluorophenyl)Methyl]-2,4-dioxo-5-thiazolidinylidene]Methyl]phenoxy]Methyl]phenyl]-

There total 5 articles about Boronic acid, B-[4-[[4-[(Z)-[3-[(4-fluorophenyl)Methyl]-2,4-dioxo-5-thiazolidinylidene]Methyl]phenoxy]Methyl]phenyl]- 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: 81.0%

(4-((4-formylphenoxy)methyl)phenyl)boronic acid (1229652-28-1) + 3-(4-fluorobenzyl)-1,3-thiazolane-2,4-dione (137660-67-4) → [4-[[4-[(Z)-[3-[(4-fluorophenyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenoxy]methyl]phenyl]boronic acid (1312201-00-5)

Guidance literature:

With piperidine; In ethanol; for 22h; Reflux;

DOI:10.1021/jm200310q

Reference yield:

4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)benzaldehyde (1312201-10-7) → [4-[[4-[(Z)-[3-[(4-fluorophenyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenoxy]methyl]phenyl]boronic acid (1312201-00-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium periodate / tetrahydrofuran; water / 0.5 h

1.2: 4 h

2.1: piperidine / ethanol / 22 h / Reflux

With piperidine; sodium periodate; In tetrahydrofuran; ethanol; water;

DOI:10.1021/jm200310q

Reference yield:

4-((4-bromobenzyl)oxy)benzaldehyde (149833-95-4) → [4-[[4-[(Z)-[3-[(4-fluorophenyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenoxy]methyl]phenyl]boronic acid (1312201-00-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 18 h / 79.84 °C

2.1: sodium periodate / tetrahydrofuran; water / 0.5 h

2.2: 4 h

3.1: piperidine / ethanol / 22 h / Reflux

With piperidine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium periodate; potassium acetate; In tetrahydrofuran; ethanol; water; 1.1: Suzuki coupling;

DOI:10.1021/jm200310q

upstream raw materials:

(4-((4-formylphenoxy)methyl)phenyl)boronic acid

3-(4-fluorobenzyl)-1,3-thiazolane-2,4-dione

4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)benzaldehyde

4-((4-bromobenzyl)oxy)benzaldehyde

Downstream raw materials:

(4-((4-((3-(4-fluorobenzyl)-2,4-dioxothiazolidin-5-yl)methyl)phenoxy)methyl)phenyl)boronic acid

(4-((4-((3-(4-fluorobenzyl)-4-hydroxy-2-oxothiazolidin-5-yl)methyl)phenoxy)methyl)phenyl)boronic acid

(4-((4-((3-(4-Fluorobenzyl)-2-oxo-2,3-dihydrothiazol-5-yl)methyl)phenoxy)methyl)phenyl)boronic acid

Refernces