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

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

Used in Chemical Research:
Bis(2-ethylhexyl) phosphite is used as a chemical warfare simulant for studying the reaction with common ion binary ionic liquids. This application helps in understanding the behavior of such compounds in different environments and their potential impact on human health and safety.
Used in Analytical Chemistry:
Bis(2-ethylhexyl) phosphite is used as a supported liquid membrane (SLM) for electromembrane extraction (EME) of basic drugs from human plasma samples. This application aids in the efficient and selective extraction of target analytes, which is crucial for accurate analysis and detection of drugs in biological samples.
Used in Environmental and Industrial Applications:
The mass-transfer kinetics of Eu3+ and Am3+ in the bis(2-ethylhexyl) phosphite-n-dodecane-NaCl-HCl-water system have been investigated. This research is essential for understanding the behavior of these ions in various environments, which can have implications in nuclear waste management, environmental remediation, and other industrial processes.

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

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

Downstream Products

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

Relevant articles and documents

Liquid-liquid extraction of neodymium(iii) by dialkylphosphate ionic liquids from acidic medium: The importance of the ionic liquid cation

The ionic liquids 1-hexyl-3-methylimidazolium bis(2-ethylhexyl)phosphate, [C6mim][DEHP], 1-hexyl-1-methylpyrrolidinium bis(2-ethylhexyl) phosphate, [C6mpyr][DEHP], and tetrabutylammonium bis(2-ethylhexyl)phosphate, [N4444][DEHP], were prepared and characterized using 1H and 13C NMR spectroscopy. The extraction behavior of neodymium(iii) from nitrate medium by these ionic liquids, diluted with the room temperature ionic liquids 1-hexyl-3- methylimidazolium bis(trifluoromethylsulfonyl)imide, [C6mim][NTf 2], 1-hexyl-3-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide, [C6mpyr][NTf2], and tributylmethylammonium bis(trifluoromethylsulfonyl)imide, [N1444][NTf2], was studied. The distribution ratio of neodymium(iii) was measured as a function of various parameters, such as pH, concentration of the ionic liquid extractant, nature of diluents, concentration of ionic liquid cations and nitrate anions in the aqueous phase. The extraction behavior was compared with that obtained for a solution of the molecular extractant bis(2-ethylhexyl)phosphoric acid (DEHPA) in an ionic liquid diluent. The extraction of neodymium(iii) in the ionic liquids [C6mim][DEHP] and [C6mpyr][DEHP] showed markedly different extraction properties in comparison with that of the quaternary ammonium analogue [N4444][DEHP], especially concerning the pH dependence of the extraction process. These results show that the extraction process can be tuned by the selection of the ionic liquid cation. The extraction experiments also included the trivalent rare-earth ions lanthanum(iii), cerium(iii), praseodymium(iii), ytterbium(iii) and yttrium(iii). Studies of the stripping behavior and the reusability of the ionic liquids were carried out, which indicate that the ionic liquids can be reused with no loss in activity.

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.

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.

Convenient preparation of long-chain dialkyl phosphates: Synthesis of dialkyl phosphates

Reaction of phosphorus oxychloride with a primary alcohol (1.8 equiv) and triethylamine (1.8 equiv) in toluene, followed by filtration and treatment with steam, gives dialkyl phosphates in good yield and essentially free from trialkyl phosphate contamination. Georg Thieme Verlag Stuttgart · New York.

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.

Synthesis of N-phosphoamino Acids With Long Dialkoxyl Chains

In this paper, a series of N-phosphoamino acids with long dialkoxyl chains were synthesized with phosphites and amino acid esters. The data of these compounds were given.