Dimethyl trimethylsilyl phosphite

Base Information

• Chemical Name: Dimethyl trimethylsilyl phosphite
• CAS No.: 36198-87-5
• Molecular Formula: C5H15O3PSi
• Molecular Weight: 182.232
• Hs Code.: 2931900090
• European Community (EC) Number: 252-908-3
• DSSTox Substance ID: DTXSID00189763
• Nikkaji Number: J319.581C
• Wikidata: Q83061973
• Mol file: 36198-87-5.mol

Synonyms:Dimethyl trimethylsilyl phosphite;36198-87-5;Phosphorous acid, dimethyl trimethylsilyl ester;dimethyl(trimethylsilyl)phosphite;dimethyl (trimethylsilyl) phosphite;EINECS 252-908-3;DIMETHYLTRIMETHYLSILYLPHOSPHITE;SCHEMBL2380027;DTXSID00189763;MFCD00075439;AKOS015913152;Dimethyl trimethylsilyl phosphite, 95%;O,O'-Dimethyl(Trimethylsilyl)Phosphite;FT-0694964

Chemical Property of Dimethyl trimethylsilyl phosphite

Chemical Property:

• Vapor Pressure: 5.82mmHg at 25°C
• Refractive Index: n20/D 1.410(lit.)
• Boiling Point: 146.6 °C at 760 mmHg
• Flash Point: 38.9 °C
• PSA: 41.28000
• Density: 0.954 g/mL at 25 °C(lit.)
• LogP: 2.35760
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 182.05280787
• Heavy Atom Count: 10
• Complexity: 89.4

Purity/Quality:

99% ^*data from raw suppliers

Dimethyl trimethylsilyl phosphite ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 10-34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COP(OC)O[Si](C)(C)C
• Uses: Dimethyl trimethylsilyl phosphite may be used in the preparation of:protected phosphoamino acid, Fmoc-Abu(PO3Me2)-OH, used in Fmoc/solid-phase peptide synthesis phosphoenolpyruvate (PEP) via trimethylsilylation, bromination and Perkow reaction sialyl phosphonate sulfonamide phosphonates

Technology Process of Dimethyl trimethylsilyl phosphite

There total 7 articles about Dimethyl trimethylsilyl phosphite 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: 89.0%

Dimethyl phosphite (868-85-9) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → dimethyl trimethylsilyl phosphite (36198-87-5)

Guidance literature:

at 90 ℃; for 2h;

Reference yield: 75.0%

chloro-trimethyl-silane (75-77-4) + Dimethyl phosphite (868-85-9) → dimethyl trimethylsilyl phosphite (36198-87-5)

Guidance literature:

Dimethyl phosphite; With triethylamine; In dichloromethane; at 0 ℃; Inert atmosphere;

chloro-trimethyl-silane; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1039/b906808b

Reference yield: 75.0%

chloro-trimethyl-silane (75-77-4) + Dimethyl phosphite (868-85-9) → dimethyl trimethylsilyl phosphite (36198-87-5) + tetramethyl (1-(Benzylamino)-5-phenylpent-4-ene-1,3-diyl)(Z)-bis(phosphonate)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acs.joc.6b02340

upstream raw materials:

chloro-trimethyl-silane

methyl phosphite

O,O-dimethyl dithiophosphoric acid S-trimethylsilyl ester

phosphorous acid trimethyl ester

Downstream raw materials:

Dimethyl 1-(trimethylsilyloxy)-1-methylhexylphosphonat

1,1,3,3-tetramethyl-1,3-disiletane

chloro-trimethyl-silane

chloroform

Refernces

• 1、 Debrouwer, Wouter,Hertsen, Dietmar,Heugebaert, Thomas S. A.,Boydas, Esma Birsen,Van Speybroeck, Veronique,Catak, Saron,Stevens, Christian V.. "Tandem Addition of Phosphite Nucleophiles Across Unsaturated Nitrogen-Containing Systems: Mechanistic Insights on Regioselectivity". . p. 188 - 201. Retrieved 2017/04/26.
• 2、 Auberson, Yves P,Allgeier, Hans,Bischoff, Serge,Lingenhoehl, Kurt,Moretti, Robert,Schmutz, Markus. "5-Phosphonomethylquinoxalinediones as competitive NMDA receptor antagonists with a preference for the human 1A/2A, rather than 1A/2B receptor composition". . p. 1099 - 1102. Retrieved 2007/10/03.