Bis(trimethylsilyl) phosphite

Base Information

• Chemical Name: Bis(trimethylsilyl) phosphite
• CAS No.: 3663-52-3
• Molecular Formula: C6H19 O3 P Si2
• Molecular Weight: 226.36
• Hs Code.: 2931900090
• European Community (EC) Number: 621-028-5
• DSSTox Substance ID: DTXSID90596088
• Wikidata: Q82491225
• Mol file: 3663-52-3.mol

Synonyms:Bis(trimethylsilyl) phosphite;3663-52-3;2,2,6,6-Tetramethyl-3,5-dioxa-4-phospha-2,6-disilaheptan-4-olate;bis(trimethylsilyl)phosphite;DTXSID90596088;LRMDYQQIIKCKLX-UHFFFAOYSA-N

Chemical Property of Bis(trimethylsilyl) phosphite

Chemical Property:

• Refractive Index: n20/D 1.412
• Boiling Point: 77-79 °C11 mm Hg
• Flash Point: 58 °C
• PSA: 52.28000
• Density: 0.968 g/mL at 20 °C(lit.)
• LogP: 2.90860
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 225.05320950
• Heavy Atom Count: 12
• Complexity: 125

Purity/Quality:

BIS(TRIMETHYLSILYL)PHOSPHITE 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)OP([O-])O[Si](C)(C)C
• Uses: Bis(trimethylsilyl) Phosphite is used in the Todd-Atherton synthetic approach for chemical modification of tetraene macrolide antibiotic lucensomycina. It is also used as a reagent in the preparation of mono-and diphosphorus proline derivatives.

Technology Process of Bis(trimethylsilyl) phosphite

There total 6 articles about Bis(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: 92.0%

formylglycine (2491-15-8) + trimethylsilyl trifluoromethanesulfonate (27607-77-8) + tris(trimethylsilyl) phosphite (1795-31-9) → bis(trimethylsilyl) phosphonate (3663-52-3) + trimethylsilyl N-{bis[bis(trimethylsiloxy)phosphoryl]methyl}glycinate

Guidance literature:

In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.jorganchem.2018.07.007

Reference yield: 82.0%

chloro-trimethyl-silane (75-77-4) → bis(trimethylsilyl) phosphonate (3663-52-3) + tris(trimethylsilyl) phosphite (1795-31-9)

Guidance literature:

With phosphonic Acid; triethylamine; In tetrahydrofuran; diethyl ether; for 6h; Heating;

DOI:10.1021/jo00323a024

Reference yield:

tris(trimethylsilyl) phosphite (1795-31-9) → bis(trimethylsilyl) phosphonate (3663-52-3) + Tris(trimethylsilyl) phosphate (10497-05-9) + Tetrakis(trimethylsilyl) pyrophosphate (18395-45-4) + Trimethylsilyldifluorophosphat (4414-25-9) + bis(trimethylsilyl) phosphorofluoridate (5668-94-0)

Guidance literature:

With [1,3]-dioxolan-2-one; lithium hexafluorophosphate; water; Diethyl carbonate; In [D₃]acetonitrile; at 20 ℃; Glovebox; Inert atmosphere;

DOI:10.1039/c6ra06555d

upstream raw materials:

chloro-trimethyl-silane

iodomethylbenzene

methoxy(trimethylsilyloxy)phosphine

bis(trimethylsilyl)phosphonite

Downstream raw materials:

C₂₂H₅₀O₁₀P₂SSi₅

Refernces

• 1、 -. "Synthetic method of di(trimethylsilyl)phosphite". Paragraph 0053; 0054. . Retrieved 2017/07/19.
• 2、 Qi, Xin,Tao, Liang,Hahn, Hendrik,Schultz, Carola,Gallus, Dennis Roman,Cao, Xia,Nowak, Sascha,R?ser, Stephan,Li, Jie,Cekic-Laskovic, Isidora,Rad, Babak Rezaei,Winter, Martin. "Lifetime limit of tris(trimethylsilyl) phosphite as electrolyte additive for high voltage lithium ion batteries". . p. 38342 - 38349. Retrieved 2016/05/19.