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

Description

DIETHYL (2-OXOBUTYL)PHOSPHONATE 96 is an organic compound that serves as a versatile reagent in the synthesis of various organic compounds. It is characterized by its phosphonate group and a 2-oxobutyl chain, which contribute to its unique chemical properties and reactivity.

Uses

Used in the Synthesis of Organic Compounds:
DIETHYL (2-OXOBUTYL)PHOSPHONATE 96 is used as a reactant for the synthesis of various organic compounds, including:
1. Oxa(bicyclo)octanone for use in preparing cycloheptane annulated furans:
DIETHYL (2-OXOBUTYL)PHOSPHONATE 96 is used as a key intermediate in the synthesis of oxa(bicyclo)octanone, which is further utilized in the preparation of cycloheptane annulated furans. These furans have potential applications in the pharmaceutical and chemical industries.
2. Anatoxin-a and homoanatoxin via the Wittig reaction:
This phosphonate compound is employed in the Wittig reaction to synthesize anatoxin-a and homoanatoxin, which are biologically active alkaloids with potential applications in research and drug development.
3. α-Methylene-β-amino ketones:
DIETHYL (2-OXOBUTYL)PHOSPHONATE 96 is used as a starting material in the synthesis of α-methylene-β-amino ketones, which are valuable building blocks in organic chemistry and have potential applications in the synthesis of pharmaceuticals and agrochemicals.
4. 2-Amino-5-phosphonoand 2-amino-4-(phosphonomethyl)thiophenes using the Gewald reaction:
This phosphonate compound is utilized in the Gewald reaction to produce 2-amino-5-phosphonoand 2-amino-4-(phosphonomethyl)thiophenes. These compounds have potential applications in the development of new materials and pharmaceuticals.
5. Aliphatic musk odorants:
DIETHYL (2-OXOBUTYL)PHOSPHONATE 96 is used as a precursor in the synthesis of aliphatic musk odorants, which are widely used in the fragrance and perfume industry.
6. Oxoalkylphosphonates:
DIETHYL (2-OXOBUTYL)PHOSPHONATE 96 is also used in the synthesis of oxoalkylphosphonates, which have potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

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 
• 17154-15-3 2-Aethylmercapto-1--buten-(2) 
• 16486-00-3 (3-chloro-2-propenyl)phosphonate 
• 1070-97-9 (2-ethoxy-2-buten-1-yl)-phosphonic acid diethyl ester 
• 683-08-9 Diethyl methylphosphonate 
• 79-03-8 propionyl chloride 
• 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 
• 126688-01-5 diethyl (E)-2-pyrrolidinoethenylphosphonate 

Downstream Products

• 598-02-7 Diethyl phosphate 
• 89588-29-4 diethyl 1-methoxymethyl-2-oxo-n-butylphosphonate 
• 131904-15-9 [2-Oxo-1,1-bis-(2-oxo-propyl)-butyl]-phosphonic acid diethyl ester 
• 53971-30-5 diethyl phosphoric acid potassium salt 
• 131904-13-7 4-(Diethoxyphosphoryl)-2-methoxy-5-oxohept-1-ene 
• 131904-14-8 4-(Diethoxyphosphoryl)-2-methoxy-5-oxo-4-(2-methoxyprop-2-enyl)hept-1-ene 
• 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 
• 1155870-68-0 tert-Butyl (6R)-6-({5-[(1E)-3-oxopent-1-en-1-yl]-6-phenylfuro[2,3-d]pyrimidin-4-yl}oxy)heptanoate 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 109632-31-7 2-oxo-1-phenylbutylphosphonate de diethyle 

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.