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

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

Uses

Used in Pharmaceutical Industry:
TRIETHYL 3-PHOSPHONOPROPIONATE is used as a reactant for the synthesis of Sulfonyl hydroxamate derivatives, which are utilized as inhibitors of class II fructosediphosphate aldolase. This application is significant for the development of drugs targeting metabolic disorders and diseases.
TRIETHYL 3-PHOSPHONOPROPIONATE is also used as a reactant for the synthesis of Imidazole glycerol phosphate dehydratase inhibitors. These inhibitors play a crucial role in the development of therapeutic agents for various diseases, including those affecting cellular metabolism.
Furthermore, TRIETHYL 3-PHOSPHONOPROPIONATE is used as a reactant for the synthesis of Competitive N-methyl-D-aspartate (NMDA) antagonists with analgesic activity. These antagonists are essential in the development of pain relief medications and treatments for neurological disorders.
Used in Biochemical Research:
In the field of biochemical research, TRIETHYL 3-PHOSPHONOPROPIONATE is used as a reactant for the synthesis of Farnesyl phosphonate derivatives of phenylalanine. These derivatives are crucial for the inhibition of farnesyl protein transferase, an enzyme involved in the post-translational modification of proteins, which has implications in the development of drugs targeting cancer and other diseases.
Used in Organic Chemistry:
TRIETHYL 3-PHOSPHONOPROPIONATE is utilized as a reactant for condensation reactions with isobutyraldehyde. This application is vital in the synthesis of various organic compounds, contributing to the advancement of organic chemistry and the development of new materials and chemicals with potential applications in various industries.

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

• 57-57-8 β-Propiolactone 
• 122-52-1 triethyl phosphite 
• 539-74-2 Ethyl 3-bromopropionate 
• 2303-76-6 sodium diethyl phosphite 
• 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 

Downstream Products

• 15762-15-9 2r-Ethoxycarbonyl-3t-phenylpropen-⁽²⁾-phosphonsaeureethylester 
• 15762-16-0 2r-Ethoxycarbonyl-3c-phenylpropen-⁽²⁾-phosphonsaeureethylester 
• 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 
• 945593-01-1 ethyl (E)-7-(benzyloxy)hept-2-en-4-ynoate 
• 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.

Pentaco-ordinate Phosphorus Compounds by Nucleophilic Addition to Activated Alkenes

The reactions between a variety of trico-ordinate phosphorus compounds and acrylonitrile or ethyl acrylate provide a novel route to pentaco-ordinate phosphorus compounds.

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.

Polylactic acid composition

It is an object of the present invention to provide a composition which contains polylactic acid and has excellent heat stability, mechanical strength and color. The composition contains 0.001 to 0.1 part by weight of a metal catalyst and 0.001 to 0.5 part by weight of a phosphono-fatty acid ester based on 100 parts by weight of polylactic acid.

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.

Stereospecific synthesis of tetrasubstituted acrylic esters

Substantially stereospacific (E)-tetrasubstituted acrylic esters, such as STR1 where R is hydrogen alkyl, R1 is alkyl, aryl or aralkyl, R2 and R4 are alkyl, are formed from racemic mixtures of corresponding unsaturated est