Diphenyl methylphosphonate

Base Information

• Chemical Name: Diphenyl methylphosphonate
• CAS No.: 7526-26-3
• Molecular Formula: C13H13 O3 P
• Molecular Weight: 248.218
• European Community (EC) Number: 231-388-1
• DSSTox Substance ID: DTXSID2064731
• Nikkaji Number: J307.861B
• Wikidata: Q81991780
• Mol file: 7526-26-3.mol

Synonyms:Diphenyl methylphosphonate;7526-26-3;Methylphosphonic Acid Diphenyl Ester;Phosphonic acid, methyl-, diphenyl ester;[methyl(phenoxy)phosphoryl]oxybenzene;EINECS 231-388-1;Phosphonic acid, P-methyl-, diphenyl ester;EC 231-388-1;diphenylmethylphosphonate;CBMicro_008796;SCHEMBL310184;DTXSID2064731;C13H13O3P;SMSF0003627;C13-H13-O3-P;MFCD00137951;AKOS003660303;CB11813;Phosphonic acid,p-methyl-,diphenyl ester;BP-12946;BIM-0008880.P001;LS-106677;M1428

Chemical Property of Diphenyl methylphosphonate

Chemical Property:

• Vapor Pressure: 0.000132mmHg at 25°C
• Melting Point: 32.5-37.5 °C(lit.)
• Boiling Point: 344.3 °C at 760 mmHg
• Flash Point: 230 °F
• PSA: 45.34000
• Density: 1.21 g/mL at 25 °C(lit.)
• LogP: 3.96730
• Water Solubility.: 1.56g/L at 20℃
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 248.06023127
• Heavy Atom Count: 17
• Complexity: 244

Purity/Quality:

99.9% ^*data from raw suppliers

DiphenylMethylphosphonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison by ingestion.
• Hazard Codes: A poison by ingestion.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CP(=O)(OC1=CC=CC=C1)OC2=CC=CC=C2

Technology Process of Diphenyl methylphosphonate

There total 36 articles about Diphenyl methylphosphonate 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: 95.6%

methanol (67-56-1) + phosphorus trichloride (7719-12-2,52843-90-0) → dimethyl phenylphosphonite (18351-42-3) + diphenyl methylphosphonate (7526-26-3) + methoxybenzene (100-66-3)

Guidance literature:

phosphorus trichloride; phenol; at 65 - 250 ℃; for 4h;

methanol; at 204 - 260 ℃; for 2h; Product distribution / selectivity;

Reference yield: 94.0%

methylphosphonic acid dichloroanhydride (676-97-1) + phenol (108-95-2,27073-41-2) → diphenyl methylphosphonate (7526-26-3)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; Cooling with ice;

DOI:10.1021/ja803612z

Reference yield: 92.0%

triphenyl phosphite (101-02-0) + methyl iodide (74-88-4) + phenol (108-95-2,27073-41-2) → diphenyl methylphosphonate (7526-26-3)

Guidance literature:

In methanol;

upstream raw materials:

ethanol

methyltriphenoxyphosphonium iodide

diphenyl methyl phosphite

methyl iodide

Downstream raw materials:

2-(diphenoxyphosphoryl)acetic acid

diphenyl methylphosphonothioate

2,4,6-tris(4-methoxyphenyl)-2,4,6-trisulfanylene-1,3,5,2,4,6-trioxatriphosphinane

ethanethiol

Refernces

• 1、 Wang, Chao,Zhang, Lei,Mou, Zhaobiao,Feng, Wanru,Li, Zhongjing,Yang, Hongzhang,Chen, Xueyuan,Lv, Shengji,Li, Zijing. "Direct18F-Labeling of Biomolecules via Spontaneous Site-Specific Nucleophilic Substitution by F-on Phosphonate Prostheses". supporting information. p. 4261 - 4266. Retrieved 2021/05/26.
• 2、 Li, Chunya,Wang, Qi,Zhang, Jian-Qiu,Ye, Jingjing,Xie, Ju,Xu, Qing,Han, Li-Biao. "Water determines the products: An unexpected Br?nsted acid-catalyzed PO-R cleavage of P(iii) esters selectively producing P(O)-H and P(O)-R compounds". supporting information. p. 2916 - 2922. Retrieved 2019/06/18.