3699-67-0

Basic information

• Product Name: TRIETHYL 3-PHOSPHONOPROPIONATE
• Synonyms: 3-DIETHYLPHOSPHONOPROPIONIC ACID ETHYL ESTER 98+%;Diethyl[2-(ethoxycarbonyl)ethyl]phosphonate, 98 %;Ethyl 3-(diethoxyphosphoryl)propanoate, Triethyl 3-phosphonopropionate;3-(Diethoxyphosphinyl)propionic acid ethyl ester;Ethyl 3-(diethoxyphosphinyl)propionate;Ethyl 3-Diethylphosphonopropionate 3-Phosphonopropionic Acid Triethyl Ester 3-Diethylphosphonopropionic Acid Ethyl Ester;Diethyl (beta-carbethoxyethyl)phosphonate;Diethyl (beta-ethoxycarbonylethyl)phosphonate
• CAS NO: 3699-67-0
• Molecular Formula: C₉H₁₉O₅P
• Molecular Weight: 238.22
• Product Categories: Horner-Emmons Reaction;Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction;C-C Bond Formation;Horner-Wadsworth-Emmons Reagents;Olefination
• Mol File: 3699-67-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 123-124 °C3 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.094 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000545mmHg at 25°C
• Refractive Index: n20/D 1.433(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 1790966
• CAS DataBase Reference: TRIETHYL 3-PHOSPHONOPROPIONATE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIETHYL 3-PHOSPHONOPROPIONATE(3699-67-0)
• EPA Substance Registry System: TRIETHYL 3-PHOSPHONOPROPIONATE(3699-67-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 3699-67-0(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

Reactant for synthesis of: Sulfonyl hydroxamate derivatives for use as inhibitors of class ii fructosediphosphate aldolaseImidazole glycerol phosphate dehydratase inhibitorsCompetitive N-methyl-D-aspartate antagonists with analgesic activityFarnesyl phosphonate derivatives of phenylalanine for inhibition of farnesyl protein transferaseReactant for condensation reactions with isobutyraldehyde

InChI:InChI=1/C9H19O5P/c1-4-12-9(10)7-8-15(11,13-5-2)14-6-3/h4-8H2,1-3H3

Upstream product

• 539-74-2 Ethyl 3-bromopropionate 
• 122-52-1 triethyl phosphite 
• 3395-91-3 Methyl 3-bromopropionate 
• 6414-69-3 ethyl 3-iodopropanoate 
• 292638-85-8 acrylic acid methyl ester 
• 535-11-5 Ethyl 2-bromopropionate 
• 78097-85-5 ethyl 2-bromo-3-ethoxypropanoate 
• 20120-21-2 ethyl 3-(N,N-dimethylamino)propionate 
• 140-88-5 ethyl acrylate 
• 64-17-5 ethanol 
• 762-04-9 Diethyl phosphonate 
• 814-68-6 acryloyl chloride 
• 762-04-9 phosphonic acid diethyl ester 
• 623-71-2 ethyl 3-chloropropanoate 

Downstream Products

• 15762-14-8 2-Ethoxycarbonyl-3-phenyl-trans-buten-⁽²⁾-phosphonsaeureethylester 
• 15762-13-7 2-Ethoxycarbonyl-3-phenyl-cis-buten-⁽²⁾-phosphonsaeureethylester 
• 945593-01-1 ethyl (E)-7-(benzyloxy)hept-2-en-4-ynoate 
• 55849-69-9 (3-hydroxypropyl)phosphonic acid diethyl ester 
• 125155-12-6 (E)-4-Methyl-2-((E)-styryl)-pent-2-enoic acid ethyl ester 
• 125155-12-6 ethyl (Z)-4-methyl-2-((E)-styryl)pent-2-enoate 
• 180088-13-5 (S)-2-[(5E,9E)-3-(Diethoxy-phosphoryl)-6,10,14-trimethyl-pentadeca-5,9,13-trienoylamino]-3-phenyl-propionic acid methyl ester 
• 180088-14-6 (S)-2-[(5E,9E)-3-(Diethoxy-phosphoryl)-6,10,14-trimethyl-pentadeca-5,9,13-trienoylamino]-3-phenyl-propionic acid 
• 194999-36-5 (2-{2-[2-(4-Methoxy-benzyloxymethyl)-2H-[1,2,4]triazol-3-yl]-oxiranyl}-ethyl)-phosphonic acid diethyl ester 

Relevant articles and documents

The Reaction of Alkyl 3-Alkoxy-2-bromopropanoate with Triethyl Phosphite

Alkyl 3-alkoxy-2-bromopropanoate reacted with triethyl phosphite to give alkyl 2,3-bis(diethoxyphosphinyl)propanoate as the major product.

Enantioselective synthesis of putative lipiarmycin aglycon related to fidaxomicin/tiacumicin B

An enantioselective synthesis of a putative lipiarmycin aglycon was accomplished and features: 1) Brown's enantioselective alkoxyallylboration and allylation of aldehydes, 2) chain elongation by iterative Horner-Wadsworth-Emmons olefination, 3) Evans' aldol reaction and 4) an enediene ring-closing metathesis. A neighboring-group-assisted chemoselective reductive desilylation was uncovered in this study and was instrumental to the realization of the present synthesis.

Synthesis of optically-active phosphono analogs of succinates

The present invention relates to catalytic asymmetric hydrogenation of phosphorus analogs of itaconic acid to synthesize novel optically active phosphono succinates.