7598-61-0

Basic information

• Product Name: DIETHYL 2,2-DIETHOXYETHYLPHOSPHONATE
• Synonyms: Phosphonic acid, (2,2-diethoxyethyl)-, diethyl ester;LABOTEST-BB LT01148150;DIETHYL PHOSPHONOACETALDEHYDE DIETHYL ACETAL;DIETHYL PHOSPHONACETALDEHYDE DIETHYL ACETAL;DIETHYL 2,2-DIETHOXETHYLPHOSPHONATE;DIETHYL 2,2-DIETHOXY-ETHANEPHOSPHONATE;DIETHYL 2,2-DIETHOXYETHYLPHOSPHONATE;AURORA KA-1450
• CAS NO: 7598-61-0
• Molecular Formula: C₁₀H₂₃O₅P
• Molecular Weight: 254.26
• EINECS: 231-504-0
• Product Categories: Wittig Reagents;Horner-Emmons Reaction;Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction
• Mol File: 7598-61-0.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 146-149 °C14 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: colourless oil
• Density: 1.052 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.430(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Dichloromethane
• Water Solubility: Soluble in chloroform and dichloromethane. Not miscible or difficult to mix in water.
• Sensitive: Moisture Sensitive
• BRN: 1785614
• CAS DataBase Reference: DIETHYL 2,2-DIETHOXYETHYLPHOSPHONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL 2,2-DIETHOXYETHYLPHOSPHONATE(7598-61-0)
• EPA Substance Registry System: DIETHYL 2,2-DIETHOXYETHYLPHOSPHONATE(7598-61-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• F: 21
• Hazardous Substances Data: 7598-61-0(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

Uses

Different sources of media describe the Uses of 7598-61-0 differently. You can refer to the following data:
1. Diethyl 2,2-diethoxyethylphosphonate can be used as a useful wittig reagent.
2. Diethyl 2,2-diethoxyethylphosphonate is used reactant for synthesis of α,β-alkenal derivatives by two-carbon homologation, lower rim-phosphonylated rexorcinol calix[4]arenes by condensation reactions, α-Phosphovinyl radicals via a radical trapping sequence, inhibitors of reverse transcriptase via 1,3-dipolar cycloadditions and for Friedel-Crafts reactions.
3. Reactant for synthesis of:α,β-Alkenal derivatives by two-carbon homologationLower rim-phosphonylated rexorcinol calix[4]arenes by condensation reactionsα-Phosphovinyl radicals via a radical trapping sequenceInhibitors of reverse transcriptase via 1,3-dipolar cycloadditionsReactant for Friedel-Crafts reactions

InChI:InChI=1/C10H23O5P/c1-5-12-10(13-6-2)9-16(11,14-7-3)15-8-4/h10H,5-9H2,1-4H3

Upstream product

• 2032-35-1 Bromoacetaldehyde diethyl acetal 
• 122-52-1 triethyl phosphite 
• 621-62-5 chloroacetaldehyde diethyl acetal 

Downstream Products

• 1606-75-3 (2-oxoethyl)phosphonic acid diethyl ester 
• 99624-20-1 hexaethyl benzene-1,3,5-tris(phosphonate) 
• 85071-64-3 dibuthyl phosphonoacetaldehyde 
• 208511-62-0 N-[(E)-2-diethoxyphosphorylethylideneamino]-4-methyl-benzenesulfonamide 
• 20061-84-1 diethyl 2-(cyclohexylimino)ethylphosphonate 
• 98934-49-7 (3-Phenyl-1H-pyrazol-4-yl)-phosphonic acid diethyl ester 
• 212701-53-6 ((E)-1-Benzoyl-2-ethoxy-vinyl)-phosphonic acid diethyl ester 
• 79782-60-8 <2-<(phenylmethyl)amino>ethenyl>phosphonic acid diethyl ester 
• 41468-36-4 diethyl (2-aminoethyl)phosphonate 
• 41948-36-1 diethyl 2-(N,N-dimethylamino)ethylphosphonate 
• 67264-31-7 (2-anilino-ethyl)-phosphonic acid diethyl ester 
• 75104-08-4 2,6-dibenzoate of 1,3:4,5-di-O-(2-diethoxyphosphinylethylidene)galactitol 

Relevant articles and documents

Condensation of resorcinol with phosphorylated acetals, synthesis of calix[4]resorcinolarenes with phosphorus-containing alkyl fragments in the lower rim

The reaction of resorcinol with phosphorylated acetals leads to formation of calix[4]resorcinolarenes having phosphonate, phosphinate, or (phosphinothioyl)sulfanylmethyl fragments in the lower rim of the molecule. Pleiades Publishing, Inc., 2006.

Synthesis of calix[4]resorcinarenes, containing phosphoryl fragments at the lower rim of the molecule

Reaction of resorcinol with phosphorylated acetals or ethoxyvinylphosphonic acid esters in acidic media leads to calix[4]resorcinarenes, containing dialkoxyphosphoryl fragments at the lower rim of the molecule. When the alkyl substituent in alkoxy groups at phosphorus atom is not very long, a partial hydrolysis of the initially formed products takes place to give calixarenes with alkoxyhydroxyphosphoryl fragments.

Determination of the Absolute Configuration of (?)-Hydroxynitrilaphos and Related Biosynthetic Questions

The ongoing search for bioactive natural products has led to the development of new genome-based screening approaches to identify possible phosphonate producing microorganisms. From the identified phosphonate producers, several until now unknown phosphonic acid natural products were isolated, including (hydroxy)nitrilaphos (4 and 5) and (hydroxy)phosphonocystoximate (7 and 6). We present the synthesis of phosphonocystoximate via an aldoxime intermediate. Chlorination and coupling with methyl N-acetylcysteinate furnished 6 after global deprotection. The obtained experimental data confirm the previously assigned structure of the natural product. We were also able to determine the absolute configuration of (?)-hydroxynitrilaphos. Chiral resolution of diethyl cyanohydroxymethylphosphonate (24) with Noe's lactol furnished both enantiomers of 4. Conversion of (+)-24 to (R)-2-amino-1-hydroxyethylphosphonic acid by reduction of the cyano-group showed (?)-hydroxynitrilaphos ultimately to be S-configured. Further, we present a 13C-isotope labeling strategy for 4 and 5 that will possibly solve the question of whether hydroxynitrilaphos is a biosynthetic intermediate or a downstream product of hydroxyphosphonocystoximate biosynthesis.