15916-48-0

Basic information

• Product Name: DIETHYL-3-BUTENYLPHOSPHONATE 95
• Synonyms: DIETHYL-3-BUTENYLPHOSPHONATE 95;P-3-Buten-1-yl-phosphonic acid diethyl ester;Diethyl 3-butenylphosphonate 95%
• CAS NO: 15916-48-0
• Molecular Formula: C₈H₁₇O₃P
• Molecular Weight: 192.193
• Product Categories: C-C Bond Formation;Horner-Wadsworth-Emmons Reagents;Olefination
• Mol File: 15916-48-0.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 55 °C0.55 mm Hg(lit.)
• Flash Point: 222 °F
• Appearance: /
• Density: 1.005 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.053mmHg at 25°C
• Refractive Index: 1.425
• CAS DataBase Reference: DIETHYL-3-BUTENYLPHOSPHONATE 95(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL-3-BUTENYLPHOSPHONATE 95(15916-48-0)
• EPA Substance Registry System: DIETHYL-3-BUTENYLPHOSPHONATE 95(15916-48-0)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 15916-48-0(Hazardous Substances Data)

Usage

Description

DIETHYL-3-BUTENYLPHOSPHONATE 95, also known as DEBP, is an organic compound with the molecular formula C8H15O3P. It is a colorless to pale yellow liquid and is commonly used as a reagent in the synthesis of various organic compounds. DEBP is characterized by its phosphonate group, which provides unique reactivity and stability in chemical reactions.

Uses

Used in Pharmaceutical Industry:
DIETHYL-3-BUTENYLPHOSPHONATE 95 is used as a reactant for the synthesis of various pharmaceutical compounds, such as:
1. Antiviral C-5-substituted pyrimidine acyclic nucleoside phosphonates, which are selected as human thymidylate kinase substrates. These compounds have potential applications in the treatment of viral infections.
2. Antimalarial agents through the halogenation of di-Et butenylphosphonate. This process leads to the development of new antimalarial drugs that can help combat the growing resistance to existing treatments.
Used in Chemical Synthesis:
DIETHYL-3-BUTENYLPHOSPHONATE 95 is used as a reactant in the synthesis of various organic compounds, including:
1. Bicyclo[3.3.1]alkenone framework compounds by gold-catalyzed Diels-Alder reactions. These compounds have potential applications in the development of new pharmaceuticals and agrochemicals.
2. Bisphosphonate enynes, which are versatile building blocks in organic synthesis and can be used to construct complex molecular structures.
3. Phosphic derivatives of carbohydrates through chemoenzymatic synthesis. These derivatives have potential applications in the development of new drugs and bioactive compounds.
Used in Catalyst Development:
DIETHYL-3-BUTENYLPHOSPHONATE 95 is used as a reactant for the development of new catalysts in:
1. Remote supramolecular control of catalyst selectivity in hydroformylation of alkenes. This process can lead to the development of more efficient and selective catalysts for industrial applications.
2. Intermolecular metal-catalyzed carbenoid cyclopropanations. This reaction can be used to synthesize various cyclopropane-containing compounds, which are important building blocks in the pharmaceutical and agrochemical industries.

InChI:InChI=1/C8H17O3P/c1-4-7-8-12(9,10-5-2)11-6-3/h4H,1,5-8H2,2-3H3

Upstream product

• 683-08-9 Diethyl methylphosphonate 
• 106-95-6 allyl bromide 
• 110625-05-3 diethyl-1-magnesium chloride methanephosphonate 
• 5162-44-7 1-bromo-4-butene 
• 762-04-9 phosphonic acid diethyl ester 
• 122-52-1 triethyl phosphite 
• 762-04-9 Diethyl phosphonate 
• 10419-77-9 diethyl iodomethanephosphonate 
• 24850-33-7 allyltributylstanane 
• 121-45-9 phosphorous acid trimethyl ester 

Downstream Products

• 1028279-25-5 [1-(Hydroxy-diphenyl-methyl)-but-3-enyl]-phosphonic acid diethyl ester 
• 63075-64-9 diethyl (4-hydroxybutyl)phosphonate 
• 35204-91-2 1-(4-chlorophenyl)pent-4-en-1-one 
• 174832-87-2 [1-(4-Chloro-benzoyl)-but-3-enyl]-phosphonic acid diethyl ester 
• 3240-29-7 1-Phenylpent-4-en-1-one 
• 850403-52-0 (1-Benzoyl-but-3-enyl)-phosphonic acid diethyl ester 
• 26954-31-4 1-(4-methylphenyl)-4-penten-1-one 
• 3986-95-6 diethyl (3-oxopropyl)phosphonate 

Relevant articles and documents

Amino acid based prodrugs of a fosmidomycin surrogate as antimalarial and antitubercular agents

Fosmidomycin is a natural antibiotic with promising IspC (DXR, 1-deoxy-D-xylulose-5-phosphate reductoisomerase) inhibitory activity. This enzyme catalyzes the first committed step of the non-mevalonate isoprenoid biosynthesis pathway, which is essential i

Chemoselective Activation of Diethyl Phosphonates: Modular Synthesis of Biologically Relevant Phosphonylated Scaffolds

Phosphonates have garnered considerable attention for years owing to both their singular biological properties and their synthetic potential. State-of-the-art methods for the preparation of mixed phosphonates, phosphonamidates, phosphonothioates, and phos

In-chain poly(phosphonate)s via acyclic diene metathesis polycondensation

In-chain poly(phosphonate)s have been prepared via acyclic diene metathesis polymerization of three different monomers. Novel unsaturated phosphonate monomers with asymmetric structure have been developed. The monomers are accessible via a three-step synthesis that can be easily scaled up. This is the first report on poly(phosphonate)s by olefin metathesis where the stable carbon-phosphorus linkage is localized in the polymer backbone. This changes the nature of the degradation products compared to other poly(phosphoester)s. Polymers with molecular weights up to 31000 g mol-1 can be achieved and have been characterized in detail NMR spectroscopy, size exclusion chromatography, thermogravimetry, and differential scanning calorimetry. They have been also compared to structural analogues polyphosphates with respect to crystallization (SAXS, WAXS) and their rheological behavior. Also, solution grown crystals were analyzed rendering some of the herein reported poly(phosphonate)s as interesting defect poly(ethylene)-like structures.