Diethyl (2,2-diethoxyethyl)phosphonate

Base Information

• Chemical Name: Diethyl (2,2-diethoxyethyl)phosphonate
• CAS No.: 7598-61-0
• Molecular Formula: C10H23O5P
• Molecular Weight: 254.263
• Hs Code.: 29319090
• European Community (EC) Number: 231-504-0
• NSC Number: 407851,77101
• UNII: KS6N6SP2MG
• DSSTox Substance ID: DTXSID20226881
• Nikkaji Number: J307.892B
• Wikidata: Q83106457
• ChEMBL ID: CHEMBL105079
• Mol file: 7598-61-0.mol

Synonyms:7598-61-0;Diethyl (2,2-diethoxyethyl)phosphonate;Diethyl 2,2-diethoxyethylphosphonate;diethyl(2,2-diethoxyethyl)phosphonate;2-diethoxyphosphoryl-1,1-diethoxyethane;CHEMBL105079;Diethyl 2,2-Diethoxethylphosphonate;EINECS 231-504-0;NSC-77101;Phosphonic acid, (2,2-diethoxyethyl)-, diethyl ester;NSC-407851;Diethylphosphonoacetaldehyde Diethyl Acetal;2,2-Diethoxyethylphosphonic Acid Diethyl Ester;phosphonic acid, P-(2,2-diethoxyethyl)-, diethyl ester;C10H23O5P;Diethyl phosphonacetaldehyde diethyl acetal;KS6N6SP2MG;SCHEMBL508153;DTXSID20226881;NSC77101;BDBM50366975;MFCD00009236;NSC 77101;NSC407851;AKOS005257029;CS-W012596;NSC 407851;diethylphosphonoacetaldehyde diethylacetal;AS-63194;Diethyl P-(2,2-diethoxyethyl)phosphonate;Diethyl 2,2-diethoxyethylphosphonate, 95%;D2423;FT-0609221;D90063;A850196;(2,2-Diethoxy-ethyl)-phosphonic acid diethyl ester;Phosphonic acid,p-(2,2-diethoxyethyl)-,diethyl ester

Chemical Property of Diethyl (2,2-diethoxyethyl)phosphonate

Chemical Property:

• Appearance/Colour: colourless oil
• Refractive Index: n20/D 1.430(lit.)
• Boiling Point: 281.2 °C at 760 mmHg
• Flash Point: 155.5 °C
• PSA: 63.80000
• Density: 1.043 g/cm³
• LogP: 2.65160
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Chloroform, Dichloromethane
• Water Solubility.: Soluble in chloroform and dichloromethane. Not miscible or difficult to mix in water.
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 254.12831083
• Heavy Atom Count: 16
• Complexity: 193

Purity/Quality:

98% ^*data from raw suppliers

Diethyl2,2-Diethoxethylphosphonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(CP(=O)(OCC)OCC)OCC
• Uses: Diethyl 2,2-diethoxyethylphosphonate can be used as a useful wittig reagent. 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. 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

Technology Process of Diethyl (2,2-diethoxyethyl)phosphonate

There total 5 articles about Diethyl (2,2-diethoxyethyl)phosphonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

Bromoacetaldehyde diethyl acetal (2032-35-1) + triethyl phosphite (122-52-1) → diethyl phosphonoacetaldehyde diethyl acetal (7598-61-0)

Guidance literature:

Reference yield:

Bromoacetaldehyde diethyl acetal (2032-35-1) + triethyl phosphite (122-52-1) → ethyl bromide (74-96-4) + diethyl phosphonoacetaldehyde diethyl acetal (7598-61-0)

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given; 1) 142-145 deg C, 4h, 2) 165-168 deg C, 1h;

DOI:10.1016/S0040-4020(01)92454-8

Reference yield:

→ ethyl bromide (74-96-4) + diethyl phosphonoacetaldehyde diethyl acetal (7598-61-0)

Guidance literature:

upstream raw materials:

Bromoacetaldehyde diethyl acetal

triethyl phosphite

chloroacetaldehyde diethyl acetal

Downstream raw materials:

(2-oxoethyl)phosphonic acid diethyl ester

hexaethyl benzene-1,3,5-tris(phosphonate)

dibuthyl phosphonoacetaldehyde

N-[(E)-2-diethoxyphosphorylethylideneamino]-4-methyl-benzenesulfonamide

Refernces

• 1、 Iorga, Bogdan,Eymery, Frederic,Mouries, Virginie,Savignac, Philippe. "Phosphorylated aldehydes: Preparations and synthetic uses". . p. 14637 - 14677. Retrieved 1998.
• 2、 Pallitsch, Katharina,Rogers, Megan P.,Andrews, Forest H.,Hammerschmidt, Friedrich,McLeish, Michael J.. "Phosphonodifluoropyruvate is a mechanism-based inhibitor of phosphonopyruvate decarboxylase from Bacteroides fragilis". supporting information. p. 4368 - 4374. Retrieved 2017/07/22.
• 3、 Dayde, Benedicte,Benzaria, Samira,Pierra, Claire,Gosselin, Gilles,Surleraux, Dominique,Volle, Jean-Noel,Pirat, Jean-Luc,Virieux, David. "Synthesis of a new family of acyclic nucleoside phosphonates, analogues of TPases transition states". experimental part. p. 3448 - 3454. Retrieved 2012/05/31.