3699-66-9

Basic information

• Product Name: TRIETHYL 2-PHOSPHONOPROPIONATE
• Synonyms: TRIETHYL 2-PHOSPHONOPROPIONATE;2-DIETHYLPHOSPHONOPROPIONIC ACID ETHYL ESTER;DIETHYL ETHOXYCARBONYLETHYL-PHOSPHONATE;ETHYL-2-(DIETHYLPHOSPHONO)PROPANOATE;Diethyl 1-(ethoxycarbonyl)ethanephosphonate~2-Phosphonopropionic acid triethyl ester;Triethyl2-phosphonopropionate,98%;2-phosphonopropionic acid triethyl ester;diethyl 1-(ethoxycarbonyl)ethanephosphonate
• CAS NO: 3699-66-9
• Molecular Formula: C₉H₁₉O₅P
• Molecular Weight: 238.22
• EINECS: 223-033-4
• Product Categories: Small molecule;C-C Bond Formation;Horner-Wadsworth-Emmons Reagents;Olefination;LJ
• Mol File: 3699-66-9.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 143-144 °C12 mm Hg(lit.)
• Flash Point: 192 °F
• Appearance: Clear colorless/Liquid
• Density: 1.111 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00507mmHg at 25°C
• Refractive Index: n20/D 1.431(lit.)
• Storage Temp.: -20°C
• Solubility: Miscible with chloroform and methanol.
• BRN: 1786994
• CAS DataBase Reference: TRIETHYL 2-PHOSPHONOPROPIONATE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIETHYL 2-PHOSPHONOPROPIONATE(3699-66-9)
• EPA Substance Registry System: TRIETHYL 2-PHOSPHONOPROPIONATE(3699-66-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-38-37-36
• Safety Statements: 23-24/25-36-26-39-37
• RIDADR: 1993
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 3699-66-9(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

Different sources of media describe the Uses of 3699-66-9 differently. You can refer to the following data:
1. Triethyl 2-Phosphonopropionate is used in studies involving insecticides and their efficacy on various bacterium. Also act as inhibitors of Epstein-Bar virus transmission and infections.
2. Triethyl 2-phosphonopropionate is used as a reactant in intramolecular conjugate addition for the synthesis of floresolide B, enantioselective synthesis of spiroindane di-methyl acetic acid and in stereo selective intramolecular Diels-Alder reactions. It plays an important role in Horner-Wadsworth-Emmons reactions and chemoenzymatic one-pot synthesis of gamma-butyrolactones. It is also used in the preparation of 3-[2]furyl-2-methyl-acrylic acid ethyl ester by reacting with furfural.

Purification Methods

Purify it by fractional distillation with high reflux ratio, preferably using a spinning band column. [Kosolapoff & Powell J Am Chem Soc 72 4198 1950, Kresze et al. Justus Liebigs Ann Chem 756 112 1972, Beilstein 4 IV 3617.]

InChI:InChI=1/C9H19O5P/c1-5-12-9(10)8(4)15(11,13-6-2)14-7-3/h8H,5-7H2,1-4H3/t8-/m0/s1

Upstream product

• 2303-76-6 sodium diethyl phosphite 
• 535-11-5 Ethyl 2-bromopropionate 
• 122-52-1 triethyl phosphite 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 123-11-5 4-methoxy-benzaldehyde 
• 101834-91-7 chloro-2 phosphono-2 propionate de triethyle 
• 101834-92-8 bromo-2 phosphono-2 propionate de triethyle 
• 814-49-3 diethyl chlorophosphate 
• 105-37-3 Ethyl propionate 
• 60-29-7 diethyl ether 
• 74-83-9 methyl bromide 
• 101834-90-6 bromo chloro phosphonoacetate de diethyle 
• 74-96-4 ethyl bromide 
• 78-38-6 ethylphosphonic acid diethyl ester 

Downstream Products

• 14182-67-3 2-methyl-4-phenyl-but-2-enoic acid ethyl ester 
• 138344-84-0 (E)-ethyl 2-methyl-4-phenylbut-3-enoate 
• 5717-41-9 ethyl 2-methylbuta-2,3-dienoate 
• 28658-41-5 (E)-2-(Diethoxy-phosphoryl)-2-methyl-5-oxo-hex-3-enoic acid ethyl ester 
• 114377-78-5 ethyl (E)-2-methyl-5-phenyl-pent-2-enoate 
• 114377-78-5 ethyl (Z)-2-methyl-5-phenyl-pent-2-enoate 
• 58625-96-0 ethyl 2-methyl-2-pentenoate 
• 1617-40-9 ethyl (E)-2-methyl-2-pentenoate 
• 52094-27-6 (Z)-2-Methyl-3-phenyl-2-butensaeure-ethylester 
• 52094-28-7 (E)-2-Methyl-3-phenyl-2-butensaeure-ethylester 
• 108062-63-1 2-methyl-3-p-tolyl-crotonic acid ethyl ester 
• 63896-70-8 2-[3-Isopropyl-4-methyl-4-vinyl-cyclohex-2-en-(Z)-ylidene]-propionic acid ethyl ester 
• 66397-42-0 Ethyl-2.6-dimethyl-8-(2'.5'-dimethoxyphenyl)octa-2E_.6E-dienoat 
• 52750-05-7 3-(4-methoxy-phenyl)-2-methyl-acrylic acid ethyl ester 

Relevant articles and documents

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Ravynic acid, an antibiotic polyeneyne tetramic acid from: Penicillium sp. elucidated through synthesis

A new antibiotic natural product, ravynic acid, has been isolated from a Penicillium sp. of fungus, collected from Ravensbourne National Park. The 3-acylpolyenyne tetramic acid structure was definitively elucidated via synthesis. Highlights of the synthetic method include the heat induced formation of the 3-acylphosphorane tetramic acid and a selective Wittig cross-coupling to efficiently prepare the natural compounds carbon skeleton. The natural compound was shown to inhibit the growth of Staphylococcus aureus down to concentrations of 2.5 g mL-1.

Total synthesis of (±)-merrilactone A

The total synthesis of racemic merrilactone A (a neurotrophic agent) is described, featuring simultaneous and stereospecific creation of the C4 and C5 Stereocenters via a notable silyloxyfuran Nazarov cyclization. Full details of the successful synthetic strategy are given, as well as several examples of the interesting reactivity of intermediates that were prepared and studied during the execution of the total synthesis. A detailed investigation of the Lewis acid-catalyzed Nazarov cyclization of silyloxyfurans was conducted, including a systematic study of substrate scope and limitations. In addition, experiments were conducted that suggest the participation of Lewis acidic silicon species in the Nazarov cyclization.