757-44-8

Basic information

• Product Name: DIETHYLPHOSPHATOETHYLTRIETHOXYSILANE
• Synonyms: diethylphosphatoethyltriethoxy;Diethylphosphatoethyltriethoxysilane, 92+%;Diethylphosphonic acid ethyltriethoxysilane;[2-(Triethoxysilyl)ethyl]phosphonic acid diethyl ester;2-(Triethoxysilyl)ethylphosphonic acid diethyl ester;Triethoxy[2-(diethoxyphosphinyl)ethyl]silane;(2-diethylphosphatoethyl)triethoxysilane;(2-DIETHYLPHOSPHATOETHYL)TRIETHOXYSILANE, tech-95
• CAS NO: 757-44-8
• Molecular Formula: C₁₂H₂₉O₆PSi
• Molecular Weight: 328.41
• EINECS: 212-056-5
• Mol File: 757-44-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: <0°C
• Boiling Point: 141 °C (2 mmHg)
• Flash Point: 70°C
• Appearance: /
• Density: 1.031
• Vapor Pressure: 0.00018mmHg at 25°C
• Refractive Index: 1.423-1.425
• CAS DataBase Reference: DIETHYLPHOSPHATOETHYLTRIETHOXYSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYLPHOSPHATOETHYLTRIETHOXYSILANE(757-44-8)
• EPA Substance Registry System: DIETHYLPHOSPHATOETHYLTRIETHOXYSILANE(757-44-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36/37/39
• TSCA: Yes
• Hazardous Substances Data: 757-44-8(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless liquid

InChI:InChI=1/C12H29O6PSi/c1-6-14-19(13,15-7-2)11-12-20(16-8-3,17-9-4)18-10-5/h6-12H2,1-5H3

Synthetic route

Triethoxyvinylsilane (78-08-0) + phosphonic acid diethyl ester (762-04-9) → diethyl [2-(triethoxysilyl)ethyl]phosphonate (757-44-8)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 120℃; for 1h;	38%
With di-tert-butyl peroxide
With di-tert-butyl peroxide

2-chloroethyltriethoxysilane (18279-67-9) + triethyl phosphite (122-52-1) → diethyl [2-(triethoxysilyl)ethyl]phosphonate (757-44-8)

diethyl [2-(triethoxysilyl)ethyl]phosphonate (757-44-8) → dihydroxyphosphorylethyltrihydroxysilane

Conditions	Yield
With hydrogenchloride at 90℃; for 24h;	100%

diethyl [2-(triethoxysilyl)ethyl]phosphonate (757-44-8) → C6H14F4O3PSi(1-)*H3N*H(1+)

Conditions	Yield
With ammonium hydrogen difluoride In water at 20℃;	99%

18-crown-6 ether (17455-13-9) + diethyl [2-(triethoxysilyl)ethyl]phosphonate (757-44-8) → C48H112O36P8Si8*F(1-)*C12H24KO6(1+)

Conditions	Yield
Stage #1: 18-crown-6 ether With potassium fluoride In toluene; acetonitrile at 20℃; for 0.25h; Inert atmosphere; Stage #2: diethyl [2-(triethoxysilyl)ethyl]phosphonate In water; toluene; acetonitrile at 20℃; Inert atmosphere;	89%

diethyl [2-(triethoxysilyl)ethyl]phosphonate (757-44-8) + tetrabutyl ammonium fluoride (429-41-4) → tetra-n-butylammonium octakis(diethylphosphatoethyl)octasilsesquioxane fluoride (1393730-74-9)

Conditions	Yield
In tetrahydrofuran; water; toluene at 25℃; for 16h; Solvent; Inert atmosphere;	82%

diethyl [2-(triethoxysilyl)ethyl]phosphonate (757-44-8) → C6H14F4O3PSi(1-)*K(1+)

Conditions	Yield
With potassium hydrogen bifluoride In water; acetone at 20℃; for 0.166667h;	77%

diethyl [2-(triethoxysilyl)ethyl]phosphonate (757-44-8) → diethyl [2-(trifluorosilyl)ethyl]phosphonate

Conditions	Yield
With boron trifluoride diethyl etherate Heating;	44.4%

triisopropanolamine (122-20-3) + diethyl [2-(triethoxysilyl)ethyl]phosphonate (757-44-8) → [2-(3,7,10-trimethyl-2,8,9-trioxa-5-aza-1-sila-bicyclo[3.3.3]undec-1-yl)-ethyl]-phosphonic acid diethyl ester (71682-51-4)

Conditions	Yield
Irradiation;

tetraethoxy orthosilicate (78-10-4) + diethyl [2-(triethoxysilyl)ethyl]phosphonate (757-44-8) → Polymer, co-polymerisation by sol-gel method Monomer(s): (EtO)4Si, 4; (EtO)3Si(CH2)2PO(OEt)2, 1

Conditions	Yield
With hydrogenchloride In ethanol for 24h;

tetraethoxy orthosilicate (78-10-4) + diethyl [2-(triethoxysilyl)ethyl]phosphonate (757-44-8) → Polymer, co-polymerisation by sol-gel method Monomer(s): (EtO)4Si, 10; (EtO)3Si(CH2)2PO(OEt)2, 1

Conditions	Yield
With hydrogenchloride In ethanol for 24h;

diethyl [2-(triethoxysilyl)ethyl]phosphonate (757-44-8) + 1,4-bis(triethoxysilyl)benzene (2615-18-1) → Polymer, co-polymerisation by sol-gel method Monomer(s): (EtO)3Si(CH2)2PO(OEt)2, 1; 1,4-bis(triethoxysilyl)benzene; 4

Conditions	Yield
With hydrogenchloride In tetrahydrofuran for 24h;

diethyl [2-(triethoxysilyl)ethyl]phosphonate (757-44-8) → diethoxyphosphorylethyltrihydroxysilane

Conditions	Yield
With hydrogenchloride In ethanol at 25℃;

Methyltrimethoxysilan (1185-55-3) + Hexamethyldisiloxane (107-46-0) + diethyl [2-(triethoxysilyl)ethyl]phosphonate (757-44-8) + n-hexyltrimethoxysilane (3069-19-0) → silsesquioxane (155881-77-9)

Conditions	Yield
With formic acid; 1,1,1,3,3,3-hexamethyl-disilazane In hexane

Upstream product

• 78-08-0 Triethoxyvinylsilane 
• 762-04-9 phosphonic acid diethyl ester 
• 18279-67-9 2-chloroethyltriethoxysilane 
• 122-52-1 triethyl phosphite 

Relevant articles and documents

Intramolecular O → Si donor-acceptor interaction in R 2P(=O)CH2CH2SiF3 molecules: Synthesis of dialkyl [2-(trifluorosilyl)ethyl]phosphonate and bis[(chloromethyl)dimethylsilyl] styrylphosphonate

The reaction of diethyl [2-(triethoxysilyl)ethyl]phosphonate with boron trifluoride etherate was used to synthesize diethyl [2-(trifluorosilyl)ethyl] phosphonate. The reaction of bis(trimethylsilyl) styrylphosphonate with chloro(chloromethyl)dimethylsilane gave bis[(chloromethyl)dimethylsilyl] styrylphosphonate. Multinuclear 1H, 13C, 19F, 29Si, and 31P NMR spectroscopy established the absence of a P=O → Si coordination bond in these compounds and the four-coordinate state of the silicon atom. Evidence for this finding was obtained by B3LYP/6-31G(d) quantum-chemical calculations. However, the same calculations for R2P(=O)? CH2CH2SiF3 (R = Me, Me2N) showed the presence in such molecules of an O → Si coordination bond both in the gas phase and in CHCl3 solution. The distance between the O and Si atoms in this series molecules decreases with R in the order: MeO > Me > Me2N. The axial Si-F bond length increases in the same order and parallels the order of the Hammet σ 0 m constants of these substituents, relating to their interaction with π-electron systems. Nauka/Interperiodica 2006.