814-22-2

Basic information

• Product Name: 1-diethoxyphosphoryloxypropane
• Synonyms: 1-diethoxyphosphoryloxypropane
• CAS NO: 814-22-2
• Molecular Formula: C₇H₁₇O₄P
• Molecular Weight: 0
• Mol File: 814-22-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 230.6°C at 760 mmHg
• Flash Point: 107.4°C
• Appearance: /
• Density: 1.047g/cm³
• Vapor Pressure: 0.099mmHg at 25°C
• Refractive Index: 1.411
• CAS DataBase Reference: 1-diethoxyphosphoryloxypropane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-diethoxyphosphoryloxypropane(814-22-2)
• EPA Substance Registry System: 1-diethoxyphosphoryloxypropane(814-22-2)

Safety Data

• Hazardous Substances Data: 814-22-2(Hazardous Substances Data)

Usage

Chemical composition

Contains a phosphorus atom bonded to two ethoxy (C2H5O-) groups and a phosphoryloxy (PO3-) group, as well as a three-carbon propanol (C3H7OH) chain.

Use in synthesis

Used in the production of pharmaceuticals and agrochemicals, particularly in the formation of phosphoramidates and phosphorohydrazides, which are important intermediates.

Reagent in organic synthesis

Acts as a reagent in organic synthesis, particularly in the formation of amide bonds between amino acids in peptide synthesis.

Versatile intermediate

Serves as a versatile intermediate in the modification of biomolecules and natural products for research purposes.

InChI:InChI=1/C7H17O4P/c1-4-7-11-12(8,9-5-2)10-6-3/h4-7H2,1-3H3

Upstream product

• 71-23-8 propan-1-ol 
• 38556-01-3 diethyl prop-2-enyl phosphite 
• 762-04-9 phosphonic acid diethyl ester 
• 2404-05-9 O,O-diethyl S-methyl phosphorothioate 
• 814-49-3 diethyl chlorophosphate 
• 5954-28-9 phosphoric acid diethyl ester isopropenyl ester 
• 107-08-4 1-iodo-propane 
• 54436-53-2 O,O-diethyl (2,4-dinitrophenyl) phosphate triester 

Relevant articles and documents

The Atherton-Todd reactions under sonochemical activation

Alcohols 1a-g phosphorylation is performed in the Atherton-Todd reaction conditions (mixture of diethylphosphonate and carbone tetrachloride and triethylamine under ultrasonic irradiation). The expected phosphates 2a-g are obtained in good yields.

LiI/TBHP Mediated Oxidative Cross-Coupling of P(O)–H Compounds with Phenols and Various Nucleophiles: Direct Access to the Synthesis of Organophosphates

An efficient and mild method for the direct phosphorylation of phenols, alcohols, and amines with P(O)–H has been reported by LiI/TBHP mediated oxidative cross-coupling reaction. Moreover, this protocol extended to β-keto esters for the synthesis of enol phosphates using H-phosphonates. Notably, this developed method applied for the synthesis of organopesticides such as paraoxon, cyanophos, and methyl parathion. The key features of this protocol are mild conditions, short reaction time, good functional group tolerance, and broad substrate scope.

Erratum: Cross-hetero-dehydrogenative coupling reaction of phosphites: A catalytic metal-free phosphorylation of amines and alcohols (Organic Letters (2013) 15:23 (6062) DOI: 10.1021/ol402956b)

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