1067-73-8

Basic information

• Product Name: DIETHYL (2-OXOBUTYL)PHOSPHONATE 96
• Synonyms: DIETHYL (2-OXOBUTYL)PHOSPHONATE 96;Diethyl propanoylmethylphosphonate
• CAS NO: 1067-73-8
• Molecular Formula: C₈H₁₇O₄P
• Molecular Weight: 208.192
• Product Categories: C-C Bond Formation;Horner-Wadsworth-Emmons Reagents;Olefination
• Mol File: 1067-73-8.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 280.5°C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.072 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00377mmHg at 25°C
• Refractive Index: n20/D 1.4360(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: DIETHYL (2-OXOBUTYL)PHOSPHONATE 96(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL (2-OXOBUTYL)PHOSPHONATE 96(1067-73-8)
• EPA Substance Registry System: DIETHYL (2-OXOBUTYL)PHOSPHONATE 96(1067-73-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1067-73-8(Hazardous Substances Data)

Usage

Uses

Reactant for synthesis of: Oxa(bicyclo)octanone for use in preparing cycloheptane annulated furansAnatoxin-a and homoanatoxin via the Wittig reactionα-Methylene-β-amino ketones2-Amino-5-phosphono- and 2-amino-4-(phosphonomethyl)thiophenes using the Gewald reactionAliphatic musk odorantsOxoalkylphosphonates

InChI:InChI=1/C8H17O4P/c1-4-8(9)7-13(10,11-5-2)12-6-3/h4-7H2,1-3H3

Upstream product

• 816-40-0 1-Bromo-2-butanone 
• 122-52-1 triethyl phosphite 
• 3095-06-5 diethyl 2-butynylphosphonate 
• 141-52-6 sodium ethanolate 
• 16486-00-3 (3-chloro-2-propenyl)phosphonate 
• 1070-97-9 (2-ethoxy-2-buten-1-yl)-phosphonic acid diethyl ester 
• 3095-05-4 diethyl 1,2-butadienylphosphonate 
• 72019-12-6 Diethyl 2-hydroxy-butanephosphonate 
• 34170-81-5 diethyl (2-chloro-2-oxoethyl)phosphonate 
• 925-90-6 ethylmagnesium bromide 
• 811-49-4 ethyllithium 
• 557-18-6 diethylmagnesium 
• 146036-63-7 2-(diethoxyphosphinyl)-2-fluoro-acetic acid chloride 
• 101300-10-1 chloro-1 oxo-2 butylphosphonate de diethyle 

Downstream Products

• 139740-83-3 (3-Methyl-2,4-dioxo-4-phenyl-butyl)-phosphonic acid diethyl ester 
• 197517-54-7 (E)-(8S,9R)-10-Benzyloxy-8-tert-butoxy-9-methyl-dec-4-en-3-one 

Relevant articles and documents

Reaction of Diethyl Phosphorochloridite with Enolates: A General Method for Synthesis of β-Keto Phosphonates and α-Phosphono Esters through C-P Bond Formation

The reaction of ketone enolates with diethyl phosphorochloridite, followed by air oxidation of the intermediate reaction products, has proven to be a general and convenient method for preparation of β-keto phosphonates.Fourteen β-keto phosphonates have been prepared by this method, in an average yield greater than 60percent.This procedure also appears to be applicable to preparation of both α-phosphono aldehydes and α-phosphono esters.Although special precautions may be necessary to avoid aldol condensation during formation of aldehyde enolates, in two cases it was shown that the resulting enolates react readily with diethyl chlorophosphite.Finally, a set of five ethyl esters was converted to α-phosphono esters by this method.Yields of the α-phosphono esters are influenced by steric hindrance at the enolate carbon, but the average yield for this series was ca. 70percent.Because this synthetic method relies upon an electrophilic phosphorus reagent for formation of the C-P bond, it is complementary to the traditional Arbuzov synthesis.On the basis of the 21 examples presented here, it appears to be more widely applicable.

A new synthesis of 2-aryl-2-oxoalkylphosphonates from triethyl phosphonoacetate

Acylation of triethyl phosphonoacetate using magnesium ethoxide affords acyl phosphonoacetates which, on treatment with catalytic p-TsOH in water, are converted into 2-aryl-2-oxoalkylphosphonates.

Silver-Catalyzed Oxidative C(sp3)?P Bond Formation through C?C and P?H Bond Cleavage

The silver-catalyzed oxidative C(sp3)?H/P?H cross-coupling of 1,3-dicarbonyl compounds with H-phosphonates, followed by a chemo- and regioselective C(sp3)?C(CO) bond-cleavage step, provided heavily functionalized β-ketophosphonates. This novel method based on a readily available reaction system exhibits wide scope, high functional-group tolerance, and exclusive selectivity.

Addition of secondary amines to alkynylphosphonates

Addition of secondary amines to alkynylphosphonates catalyzed by Cu(I) salts proceeds regio- and stereospecifically to form (E)-2-(dialkylamino)alkenylphosphonates. The E-configuration was proved by analysis of 13C-31P vicinal spin-spin coupling constants in the NMR spectra of the products and authentic model compounds. The 3JPC constants in the model compounds fall in the range of 6-12 Hz for the cis arrangement of the coupled nuclei and are equal to or higher than 16 Hz for the trans configuration. Related coupling constants in the addition products are around 5 Hz, that is, corresponding to cis coupling.