21646-99-1

Basic information

• Product Name: TETRAETHYL PYROPHOSPHITE
• Synonyms: TETRAETHYL PYROPHOSPHITE;TETRAETHYL PYROPHOSPHITE, TECH., 93%;Bis(diethoxyphosphino) ether;Bis(phosphorous acid diethyl)anhydride;Diphosphorous acid tetraethyl ester;Oxybis(diethoxyphosphine);Oxybis(phosphonous acid diethyl) ester;Tetraethyl pyrophosphite,93%,tech.
• CAS NO: 21646-99-1
• Molecular Formula: C₈H₂₀O₅P₂
• Molecular Weight: 258.19
• EINECS: 244-494-8
• Product Categories: Organic Building Blocks;Organic Phosphates/Phosphites;Phosphorus Compounds
• Mol File: 21646-99-1.mol

Chemical Properties

• Boiling Point: 79-81 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.057 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0674mmHg at 25°C
• Refractive Index: n20/D 1.434(lit.)
• Solubility: Chloroform (Slightly), DMSO (Sparingly), Methanol (Slightly)
• CAS DataBase Reference: TETRAETHYL PYROPHOSPHITE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAETHYL PYROPHOSPHITE(21646-99-1)
• EPA Substance Registry System: TETRAETHYL PYROPHOSPHITE(21646-99-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 21646-99-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
TETRAETHYL PYROPHOSPHITE is used as a reagent for peptide synthesis, playing a crucial role in the formation and modification of peptide bonds. This application is significant in the development of new pharmaceuticals and the study of protein structures.
Used in the Preparation of Peptides:
TETRAETHYL PYROPHOSPHITE is utilized in the preparation of peptides, where it aids in the formation of peptide bonds between amino acid residues. This process is essential for the synthesis of various peptides and proteins, which have potential applications in medicine, biotechnology, and other related fields.
Used in the Phosphonylation of Carbonyl Compounds:
In addition to its role in peptide synthesis, TETRAETHYL PYROPHOSPHITE is also used in the phosphonylation of carbonyl compounds. This reaction is important for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Overall, TETRAETHYL PYROPHOSPHITE is a valuable reagent in the fields of organic chemistry, pharmaceuticals, and biotechnology, thanks to its diverse applications in peptide synthesis and the modification of carbonyl compounds.

InChI:InChI=1/C8H20O5P2/c1-5-9-14(10-6-2)13-15(11-7-3)12-8-4/h5-8H2,1-4H3

Upstream product

• 589-57-1 diethyl phosphorylchloridite 
• 762-04-9 phosphonic acid diethyl ester 
• 17507-52-7 O,O-diethyl (triethoxymethyl)phosphonate 
• 17997-33-0 diethyl(diethoxymethyl)phosphonate 
• 20502-85-6 diethyl hydrogen phosphite 
• 2303-76-6 sodium diethyl phosphite 
• 74756-79-9 C₁₀H₂₅NO₄P₂ 
• 122-52-1 triethyl phosphite 
• 108-85-0 1-bromocyclohexane 
• 682-24-6 diphosphorus (III,V)-oic acid tetraethyl ester 
• 762-04-9 Diethyl phosphonate 
• 814-49-3 diethyl chlorophosphate 
• 60-29-7 diethyl ether 
• 7726-95-6 bromine 

Downstream Products

• 589-57-1 diethyl phosphorylchloridite 
• 866-23-9 diethyl (trichloromethyl)phosphonate 
• 814-49-3 diethyl chlorophosphate 
• 166660-56-6 triphenylmethylphosphinic acid 
• 121255-30-9 4-{[N⁶-benzyloxycarbonyl-N²-(toluene-4-sulfonyl)-L-lysyl]-amino}-benzoic acid benzyl ester 
• 856799-98-9 N-diethoxyphosphino-phenylalanine ethyl ester 
• 3689-24-5 sulfotep 
• 71572-20-8 α-(diethoxyphosphinyl)benzyl diethyl phosphite 
• 20998-88-3 N-benzyloxycarbonyl-phenylalanine p-toluidide 
• 40648-77-9 p-toluoyl-phosphorous acid diethyl ester 
• 102750-17-4 4-[(N-benzyloxycarbonyl-glycyl)-amino]-benzoic acid benzyl ester 
• 40648-79-1 diethyl benzoyl phosphite 
• 7801-64-1 N-(N-benzyloxycarbonyl-phenylalanyl)-glycine ethyl ester 
• 96677-54-2 Phosphorigsaeure-diaethylester-<4-nitro-anilid> 

Relevant articles and documents

Reinvestigation of the reaction between sodium diethyl phosphite and diethyl phosphorochloridate. Evidence for a SET process in the formation of a direct P(IV)-P(IV) bond

Alkali metal salts of diethyl phosphites act as nucleophiles or electron donors in reactions with diethyl phosphorochloridate. Evidence is provided that formation of the direct P(IV)-P(IV) bond proceeds via a single electron transfer process (SET) from phosphite anion to phosphorochloridate.

Reaction of (chloromethyl)phosphonic(-phosphinic) chlorides with silylated protic nucleophiles

Reactions of (chloromethyl)phosphonic(-hosphinic) chlorides with trimethylalkoxy(-phenoxy, -dialkylamino)silanes are accompanied by elimination of trimethylchlorosilane and lead to formation of related substitution products. Reactions of bis(chloromethyl)phosphinic chloride and (chloromethyl)phosphinic dichloride with neutral and hydrogen silyl phosphites were studied. The reactions of bis(chloromethyl)phosphinic chloride with tris(trimethylsilyl)phosphite, diethyl trimethylsilyl phosphite, and bis(trimethylsilyl) hydrogen phosphite yield trimethylsilyl bis(chloromethyl)phosphinate. Similar reactions with (chloromethyl)phosphonic dichloride resulted in isolation of bis(trimethylsilyl) (chloromethyl)phosphonate.

Electrochemical Oxidation of Metal Dialkyl Phosphites and Their Reaction with Halogens

Electrochemical oxidation of sodium dialkyl phosphites with alkyl radicals of normal structure leads to formation of tetraalkyl pyrophosphites as the main products, while electrochemical oxidation of litium dialkyl phosphites and sodium salts with branched alkyl radicals yields tetraalkyl hypophosphates. The reaction of metal dialkyl phosphites with halogens leads to analogous results.

Aryl H-phosphonates. 7. Studies on the formation of phosphorus-carbon bond in the reaction of trityl and benzyl halides with dialkyl and diphenyl H-phosphonates

The reactions of H-phosphonate diesters with trityl and benzyl halides were investigated using 31P NMR spectroscopy. It was found that extensive oxidation, which usually accompanies the formation of trityl- or p-nitrobenzylphosphonates from the corresponding alkyl bromides in the Michaelis-Becker reaction, can be considerably suppressed or completely eliminated by reacting p-nitrobenzyl or trityl bromides with diphenyl H-phosphonate in acetonitrile in the presence of DBU.

Free-Radical Phosphorylation of Olefins Initiated by Anodic Oxidation

Electrochemical oxidation of lithium and sodium dialkyl phosphites generates dialkyl phosphonyl radicals, which initiate chain free-radical addition of dialkyl phosphites across the alkene multiple bond to form alkyl(cycloalkyl)phosphonates. Alkyl(cycloalkyl)phosphonates are formed simultaneously owing to anodic oxidation of adsorbed primary radical adducts of phosphonyl radical and alkene molecule to give the carbenium cation, followed by deprotonation of the latter.

Anomalous Michaelis-Becker Reaction: 1-Phenylethan-1,2,2-triphosphonic Acid and their Esters

Sodium dialkylphosphite reacts with trichlorovinylbenzene to yield in an one-batch procedure 1-phenyl-1,2,2-ethanetriphosphonic acid hexaalkyl esters.A carbanionic intermediate of an "anomalous Michaelis-Becker reaction" is deduced.Acidolysis of esters leads to the parent triphosphonic acids.NMR parameters of this acid are strongly influenced by protolytic equilibrium. - Key words: One-batch synthesis, Oligophosphonic Acid, NMR Spectra