3658-48-8

Basic information

• Product Name: BIS(2-ETHYLHEXYL) PHOSPHITE
• Synonyms: Bis(2-ethyl-1-hexyl) phosphite;Bis(2-ethylhexyl) phosphonate;bis(2-ethylhexyl)phosphonate;bis(2-ethylhexyl)phosphonicacid;chelexh8;di-2-ethylhexylhydrogenphosphite;diisooctylphosphite;Dioctyl (2-ethylhexyl) phosphite
• CAS NO: 3658-48-8
• Molecular Formula: C₁₆H₃₅O₃P
• Molecular Weight: 306.42
• EINECS: 222-904-6
• Product Categories: Organic Building Blocks;Organic Phosphates/Phosphites;Phosphorus Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Organic Phosphates/Phosphites;Phosphorus Compounds
• Mol File: 3658-48-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 395.2°Cat760mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 0.916 g/mL at 25 °C(lit.)
• Vapor Pressure: 0-0.009Pa at 20-50℃
• Refractive Index: n20/D 1.442(lit.)
• CAS DataBase Reference: BIS(2-ETHYLHEXYL) PHOSPHITE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(2-ETHYLHEXYL) PHOSPHITE(3658-48-8)
• EPA Substance Registry System: BIS(2-ETHYLHEXYL) PHOSPHITE(3658-48-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 2
• RTECS: SZ6840000
• Hazardous Substances Data: 3658-48-8(Hazardous Substances Data)

Usage

Uses

Bis(2-ethylhexyl) Phosphite is used as a supported liquid membranes (SLMs) for electromembrane extraction (EME) of basic drugs from human plasma samples.

General Description

Bis(2-ethylhexyl) phosphite is an chemical warfare simulant and its reaction with common ion binary ionic liquid has been investigated. Mass-transfer kinetics of Eu3+ and Am3+ in bis(2-ethylhexyl) phosphite-n-dodecane-NaCl-HCl-water system has been investigated.

InChI:InChI=1/C16H34O3P/c1-5-9-11-15(7-3)13-18-20(17)19-14-16(8-4)12-10-6-2/h15-16H,5-14H2,1-4H3/q+1

Synthetic route

2-Ethylhexyl alcohol (104-76-7) → bis(2-ethylhexyl)phosphite (3658-48-8)

Conditions	Yield
With phosphorus trichloride In benzene at 20℃; for 2h; Condensation;	96%
With phosphorus trichloride at 20℃; for 2h;	85.8%
With phosphonic acid; toluene

methyl phosphite (96-36-6, 868-85-9) + 2-Ethylhexyl alcohol (104-76-7) → bis(2-ethylhexyl)phosphite (3658-48-8)

Conditions	Yield
With sodium at 160℃;

2-Ethylhexyl alcohol (104-76-7) + phosphonic acid diethyl ester (762-04-9) → bis(2-ethylhexyl)phosphite (3658-48-8)

Conditions	Yield
With sodium at 160℃;
With sodium hydride In mineral oil at 160℃;

2-Ethylhexyl alcohol (104-76-7) + diphenylphosphonate → bis(2-ethylhexyl)phosphite (3658-48-8)

Conditions	Yield

2-Ethylhexyl alcohol (104-76-7) + mono-2-ethyl-1-hexyl phosphite → bis(2-ethylhexyl)phosphite (3658-48-8)

Conditions	Yield
Stage #1: mono-2-ethyl-1-hexyl phosphite With phosphorus pentoxide at 54℃; for 3h; Inert atmosphere; Stage #2: 2-Ethylhexyl alcohol at 56℃; for 0.5h; Inert atmosphere;	46.2 %Spectr.

bis(2-ethylhexyl)phosphite (3658-48-8) → bis(2-ethylhexyl) phosphorochloridate (63449-80-9)

Conditions	Yield
With N-chloro-succinimide at -78 - 20℃; Inert atmosphere; neat (no solvent);	97%
With chlorine
With sulfuryl dichloride

benzophenone (119-61-9) + bis(2-ethylhexyl)phosphite (3658-48-8) → C29H45O4P

Conditions	Yield
Stage #1: benzophenone; bis(2-ethylhexyl)phosphite With calcium fluoride for 0.0833333h; Stage #2: With potassium hydroxide at 40 - 50℃; for 2.16667h;	97%

formaldehyd (50-00-0) + bis(2-ethylhexyl)phosphite (3658-48-8) + benzylamine (100-46-9) → O,O-di(2-ethylhexyl) 1-(benzylamino)methylphosphonate

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 12h; Heating;	95%

bis(2-ethylhexyl)phosphite (3658-48-8) + butanone (78-93-3) → C20H43O4P

Conditions	Yield
Stage #1: bis(2-ethylhexyl)phosphite; butanone With calcium fluoride for 0.0833333h; Stage #2: With potassium hydroxide at 40 - 50℃; for 2.16667h;	92.5%

bis(2-ethylhexyl)phosphite (3658-48-8) + dibutylamine (111-92-2) → bis(2-ethylhexyl) dibutylphosphoramidate

Conditions	Yield
With tetrachloromethane In hexane Todd-Atherton reaction;	88%

bis(2-ethylhexyl)phosphite (3658-48-8) + acetone (67-64-1) + benzylamine (100-46-9) → O,O-di(2-ethylhexyl) 1-(benzylamino)-1-methylethylphosphonate

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 80℃; for 12h;	87%

bis(2-ethylhexyl)phosphite (3658-48-8) + diethylamine (109-89-7) → bis(2-ethylhexyl) diethylphosphoramidate

Conditions	Yield
With tetrachloromethane at 0 - 20℃; for 1.5h; Todd-Atherton reaction;	87%

bis(2-ethylhexyl)phosphite (3658-48-8) + N-butylamine (109-73-9) → bis(2-ethylhexyl) butylphosphoramidate (53796-11-5)

Conditions	Yield
With tetrachloromethane In hexane Todd-Atherton reaction;	86%

bis(2-ethylhexyl)phosphite (3658-48-8) + phenylpropynoic acid ethyl ester (2216-94-6) → (E)-ethyl 2-(bis(2-ethylhexyloxy)phosphoryl)-3-phenylacrylate

Conditions	Yield
With tributylphosphine In acetonitrile at 20℃; for 1.16667h; stereoselective reaction;	84%

cobaltocene (1277-43-6) + bis(2-ethylhexyl)phosphite (3658-48-8) → bis[cyclopentadienyltris(bis(2-ethylhexyl) phosphito-P)cobalt-O,O',O'']cobalt(II)

Conditions	Yield
In neat (no solvent) byproducts: cyclopentadiene; (N2); 140°C, 40 h; removal of cyclopentadiene by distn., stirring with MeOH, filtration, drying (reduced pressure), chromy. (SiO2; hexane, then MeOH), evapn., dissoln. (hexane), membrane filtration, evapn.;	83%

bis(2-ethylhexyl)phosphite (3658-48-8) + 1-hexyl-3-methylimidazol-1-ium chloride (171058-17-6) → 1-hexyl-3-methylimidazolium bis(2-ethylhexyl)phosphate

Conditions	Yield
With dihydrogen peroxide; sodium hydroxide In dichloromethane for 24h;	82%

bis(2-ethylhexyl)phosphite (3658-48-8) + 2-Chloro-N,N-diethylacetamide (2315-36-8) → bis(2-ethyl-1-hexyl) (N,N-diethylcarbamoylmethyl)phosphonate (66258-31-9)

Conditions	Yield
With potassium hydroxide; potassium carbonate In benzene for 6h; Product distribution; Ambient temperature; other diarylphosphine oxides and dialkyl hydrogen phosphites, var. alkylating agents, var. reaction times, also in the presence 18-crown-6, and phase transfer catalysis;	80%
With potassium hydroxide; potassium carbonate In benzene for 6h; Ambient temperature;	80%
With sodium hydroxide; Aliquat 336 In dichloromethane at 20 - 25℃; for 5.5h; Yield given;

(E)-2-decenol (18409-18-2) + bis(2-ethylhexyl)phosphite (3658-48-8) → (2E)-dec-2-en-1-yl bis(2-ethylhexyl) phosphate (1542073-82-4)

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In tetrachloromethane; dichloromethane; water at 0℃; for 35h; Inert atmosphere;	80%

bis(2-ethylhexyl)phosphite (3658-48-8) + tert-Butyl chloroacetate (107-59-5) → [Bis-(2-ethyl-hexyloxy)-phosphoryl]-acetic acid tert-butyl ester (103717-36-8)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane at 0 - 5℃; for 5h;	79%

Upstream product

• 104-76-7 2-Ethylhexyl alcohol 
• 762-04-9 phosphonic acid diethyl ester 
• 96-36-6 methyl phosphite 

Downstream Products

• 52894-02-7 bis(2-ethylhexyl) octylphosphonate 
• 1542074-04-3 bis(2-ethylhexyl) (2E)-3-[4-(methyl)phenyl]prop-2-en-1-yl phosphate 
• 1542073-99-3 bis(2-ethylhexyl) (2E)-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-ylphosphate 
• 1542074-11-2 bis(2-ethylhexyl) (2E)-hex-2-en-1-yl phosphate 
• 1542075-04-6 (+)-(1R)-1-cyclohexylprop-2-en-1-yl (2E)-but-2-enoate 
• 1240492-42-5 bis(2-ethylhexyl) (2E)-3-phenylprop-2-en-1-yl phosphate 
• 1542075-20-6 (+)-(1R)-1-phenylprop-2-en-1-yl (2E,4E)-hexa-2,4-dienoate 
• 1028346-85-1 C₂₅H₄₆NO₃P 
• 178943-99-2 (1-Fluoro-3-phenyl-prop-2-ynyl)-phosphonic acid bis-(2-ethyl-hexyl) ester 
• 103717-37-9 [Bis-(2-ethyl-hexyloxy)-phosphoryl]-acetic acid cyclohexyl ester 
• 63449-80-9 bis(2-ethylhexyl) phosphorochloridate 
• 298-07-7 Bis(2-ethylhexyl)phosphoric acid 

Relevant articles and documents

Method for the esterification of P-O components

The present invention is directed to a new method for esterification of P-O components. More specifically, the present invention relates to a new method for esterification of P-O components containing at least one P-O-H functional group, whereby the P-O-H functional group(s) is converted into P-O-R functional group(s). The method according to the invention may find particular use in the manufacture of diesters of phosphorous acid.

A convenient two-step synthesis of dialkylphosphate ionic liquids

Dialkylphosphate ionic liquids are useful solvents for cellulose dissolution and catalytic reactions. In this paper, a new methodology for the synthesis of hydrophobic phosphate-based ionic liquids is described. This method involves the oxidation reaction of an easily prepared H-phosphonate precursor by using the environmentally friendly and inexpensive oxidizing agent hydrogen peroxide.

ORGANOPHOSPHORUS COMPOUND HAVING PHOSPHATE-PHOSPHONATE BOND, AND FLAME-RETARDANT POLYESTER FIBER AND FLAME-RETARDANT POLYURETHANE RESIN COMPOSITION EACH CONTAINING THE SAME

The present invention provides a phosphate-phosphonate compound which has a low volatility and a high phosphorus content, does not exert adverse influences on the physical properties of a product containing the phosphate-phosphonate compound as a material, and is recyclable and causes substantially no environmental load since a halogen atom such as a chlorine atom or a bromine atom is not included. A phosphorus compound containing a phosphate-phosphonate bond in one molecule and having a specific structure has a high flame retarding property. By using a phosphate-phosphonate compound as a flame retarding agent for a polyurethane or for a polyester, preferable plasticity and flame retarding property are obtained. Such a flame retardant agent exerts substantially no adverse influences on the physical properties of a polyurethane foam or a polyester fiber.