Benzyl Dimethylphosphonoacetate

Base Information

• Chemical Name: Benzyl Dimethylphosphonoacetate
• CAS No.: 57443-18-2
• Molecular Formula: C11H15O5P
• Molecular Weight: 258.211
• Hs Code.: 29310099
• European Community (EC) Number: 678-185-8
• DSSTox Substance ID: DTXSID60378691
• Nikkaji Number: J2.283.357J
• Wikidata: Q72441108
• Mol file: 57443-18-2.mol

Synonyms:57443-18-2;Benzyl Dimethylphosphonoacetate;benzyl 2-dimethoxyphosphorylacetate;benzyl 2-(dimethoxyphosphoryl)acetate;BENZYL DIMETHYL PHOSPHONOACETATE;Dimethyl(benzyloxycarbonyl)methyl phosphonate;Acetic acid, (dimethoxyphosphinyl)-, phenylmethyl ester;Dimethyl (benzyloxycarbonyl)methylphosphonate;benzyl dimethylphosphonoethanoate;SCHEMBL4465319;Dimethyl (Cbz-methyl)phosphonate;benzyl(dimethoxyphosphoryl)acetate;DTXSID60378691;QYLGNJMIOVHLQQ-UHFFFAOYSA-N;benzyl (dimethoxyphosphoryl)acetate;BBL102424;benzyl 2-(dimethyl phosphono)acetate;benzyl-2-(dimethoxyphosphoryl)acetate;GEO-02882;MFCD01872507;STL556226;AKOS017343609;Dimethylphosphonoacetic Acid Benzyl Ester;PS-11110;dimethyl(benzyloxycarbonyl)methylphosphonate;(Dimethoxyphosphinyl)acetic acid benzyl ester;(dimethoxyphosphoryl)acetic acid benzyl ester;B2815;CS-0199168;Dimethyl (Benzyloxycarbonylmethyl)phosphonate;D88966;EN300-249604;A855317

Chemical Property of Benzyl Dimethylphosphonoacetate

Chemical Property:

• Appearance/Colour: clear colorless to light brown liquid
• Vapor Pressure: 2.38E-05mmHg at 25°C
• Refractive Index: 1.505-1.507
• Boiling Point: 359.4 °C at 760 mmHg
• Flash Point: 184.8 °C
• PSA: 71.64000
• Density: 1.217 g/cm³
• LogP: 2.21570
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 258.06571057
• Heavy Atom Count: 17
• Complexity: 278

Purity/Quality:

99% ^*data from raw suppliers

Benzyl2-(Dimethoxyphosphoryl)acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COP(=O)(CC(=O)OCC1=CC=CC=C1)OC

Technology Process of Benzyl Dimethylphosphonoacetate

There total 5 articles about Benzyl Dimethylphosphonoacetate 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: 87.0%

trimethyl phosphonoacetate (5927-18-4) + benzyl alcohol (100-51-6,185532-71-2) → benzyl 2-(dimethoxyphosphoryl)acetate (57443-18-2)

Guidance literature:

With oxo[hexa(trifluoroacetato)]tetrazinc; In toluene; for 48h; Reflux; Inert atmosphere; Schlenk technique;

DOI:10.1002/asia.201600062

Reference yield: 81.0%

phosphorous acid trimethyl ester (121-45-9) + Benzyl bromoacetate (5437-45-6) → benzyl 2-(dimethoxyphosphoryl)acetate (57443-18-2) + dimethyl methane phosphonate (756-79-6)

Guidance literature:

at 85 ℃; for 60h;

DOI:10.1039/b511053j

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → benzyl 2-(dimethoxyphosphoryl)acetate (57443-18-2)

Guidance literature:

Multi-step reaction with 2 steps

1: TsOH

With toluene-4-sulfonic acid;

DOI:10.1021/jo00866a024

upstream raw materials:

phosphorous acid trimethyl ester

Benzyl bromoacetate

trimethyl phosphonoacetate

benzyl alcohol

Downstream raw materials:

(E)-3-Methyl-4-phenylselanyl-but-2-enoic acid benzyl ester

(E)-cinnamic acid benzyl ester

Benzyl 3-phenylpropionate

benzaldehyde

Refernces

The structural requirements of histone deacetylase inhibitors: Suberoylanilide hydroxamic acid analogs modified at the C6 position

10.1016/j.bmcl.2012.09.093

The research discusses the structural requirements of histone deacetylase (HDAC) inhibitors, specifically focusing on the modification of Suberoylanilide hydroxamic acid (SAHA, Vorinostat) at the C6 position to study its impact on potency and selectivity. The purpose of this study was to understand how changes at the C6 position of SAHA affect its ability to inhibit HDAC proteins, which are over-expressed in many cancers and thus potential targets for anti-cancer drugs. The researchers synthesized and evaluated SAHA analogs with various hydrophobic substituents at the C6 position, including methyl, phenyl, t-butyl, and 2-ethylhexyl groups. Their conclusions were that most C6-SAHA analogs maintained nanomolar potency, and that substituents at the C6 position could modestly influence selectivity for individual HDAC isoforms, suggesting that the linker region near the capping group is a promising area for future drug design. The chemicals used in the synthesis process included e-caprolactone, benzyl dimethyl phosphonoacetate, copper (I) iodide, methyl lithium, aniline, and various other reagents for the Horner–Wadsworth–Emmons reaction, oxidation, and hydrogenolysis steps.