Bis(hydroxyphenylmethyl)phosphinic acid

Base Information

• Chemical Name: Bis(hydroxyphenylmethyl)phosphinic acid
• CAS No.: 90-09-5
• Molecular Formula: C₁₄H₁₅O₄P
• Molecular Weight: 278.244
• DSSTox Substance ID: DTXSID101009088
• Nikkaji Number: J1.077.660K
• ChEMBL ID: CHEMBL1891887
• Mol file: 90-09-5.mol

Synonyms:bis[hydroxy(phenyl)methyl]phosphinic acid;90-09-5;Bis(hydroxyphenylmethyl)phosphinic acid;BRN 1993614;Phosphinic acid, bis(hydroxyphenylmethyl)-;Oprea1_656358;2-07-00-00176 (Beilstein Handbook Reference);MLS001243489;CHEMBL1891887;SCHEMBL11413322;DTXSID101009088;HMS2208C14;HMS3352O01;NCGC00247396-01;SMR000841541

Chemical Property of Bis(hydroxyphenylmethyl)phosphinic acid

Chemical Property:

• Vapor Pressure: 6.64E-15mmHg at 25°C
• Boiling Point: 592.9°C at 760 mmHg
• Flash Point: 312.4°C
• Density: 1.383g/cm³
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 278.07079595
• Heavy Atom Count: 19
• Complexity: 293

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(O)P(=O)(C(C2=CC=CC=C2)O)O

Technology Process of Bis(hydroxyphenylmethyl)phosphinic acid

There total 9 articles about Bis(hydroxyphenylmethyl)phosphinic 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: 95.0%

C23H39O4PSi3 (112318-35-1,112372-79-9) → bis-(α-hydroxyphenylmethyl)phosphinic acid (90-09-5,112162-61-5,112162-62-6)

Guidance literature:

With ethanol; for 0.166667h; Heating;

DOI:10.1055/s-1987-28001

Reference yield: 82.0%

benzaldehyde (100-52-7) → bis-(α-hydroxyphenylmethyl)phosphinic acid (90-09-5,112162-61-5,112162-62-6)

Guidance literature:

With hypophosphorous acid; for 0.00833333h; microwave irradiation;

DOI:10.1016/j.tetlet.2004.10.025

Reference yield: 41.0%

benzaldehyde (100-52-7) → bis-(α-hydroxyphenylmethyl)phosphinic acid (90-09-5,112162-61-5,112162-62-6) + 5-hydroxy-5-oxo-2,4,6-triphenyl-1,3,5-dioxaphosphorinane (13474-66-3)

Guidance literature:

With hypophosphorous acid; In benzene; for 3h; Heating;

DOI:10.1007/BF00963705

upstream raw materials:

benzaldehyde

C₂₃H₃₉O₄PSi₃

Downstream raw materials:

5-hydroxy-5-oxo-2,4,6-triphenyl-1,3,5-dioxaphosphorinane

dibenzylphosphinic acid

Refernces

Design and synthesis of phosphotyrosine mimetics

10.1016/S0960-894X(03)00253-1

The research focuses on the design and synthesis of phosphotyrosine mimetics, which are of significant interest as potential therapeutic agents and research tools for selectively inhibiting protein tyrosine phosphatases (PTPases). These enzymes play a crucial role in regulating tyrosine phosphorylation and cellular function, and their inhibition could have therapeutic potential for diseases such as diabetes, cancer, and osteoporosis. The study involved the synthesis of phenylalanine derivatives, designed to mimic phosphorylated tyrosine or to act as irreversible active site inhibitors of PTPases. Key chemicals used in the synthesis process included Fmoc-l-Tyr-(3-NO2)-OH, CDI, MeOH, SnCl2, phosgene, TsCl, pyridine, SO2Cl2, and various other reagents and solvents. The synthesized compounds were then incorporated into a combinatorial library and screened for their ability to inhibit four phosphatases, showing moderate potency and selectivity, with the type 2d phosphotyrosine mimetic exhibiting the best activity. However, further analysis of enzymatic inhibition was not possible due to the termination of operations at Molecumetics.