Triethyl 2-phosphonobutyrate

Base Information

• Chemical Name: Triethyl 2-phosphonobutyrate
• CAS No.: 17145-91-4
• Molecular Formula: C10H21 O5 P
• Molecular Weight: 252.247
• Hs Code.: 29310099
• European Community (EC) Number: 627-866-8
• NSC Number: 22423
• Nikkaji Number: J103.544D
• Mol file: 17145-91-4.mol

Synonyms:Triethyl 2-phosphonobutyrate;17145-91-4;Ethyl 2-(diethoxyphosphoryl)butanoate;ethyl 2-diethoxyphosphorylbutanoate;Ethyl 2-(diethylphosphono)butyrate;Butanoic acid, 2-(diethoxyphosphinyl)-, ethyl ester;Triethyl 2-phosphonobutanoate;.alpha.-(Diethylphosphono)butanoic acid, ethyl ester;MFCD00041347;Butyric acid, 2-phosphono-, triethyl ester;Butyric acid, triethyl ester;triethyl 2-phosphonobu-tyrate;Triethyl-2-phosphono butyrate;SCHEMBL1052265;ethyl 2-diethylphosphonobutanoate;GYUCVQSNZFRDRL-UHFFFAOYSA-;NSC22423;Triethyl 2-phosphonobutyrate, 98%;ethyl 2-(diethoxyphosphoryl)butyrate;Ethyl2-(diethoxyphosphoryl)butanoate;ethyl 2-(diethyl phosphono)butanoate;NSC-22423;AKOS015915825;diethyl 1-ethoxycarbonylpropylphosphonate;Ethyl 2-(diethoxyphosphoryl)butanoate #;AS-63454;SY211096;a-Diethylphosphonobutanoic acid ethyl ester;ethyl 2-(diethoxyphosphoryl)-2-ethylacetate;CS-0148079;EN300-378863;A921676;J-010727;2-(DIETHOXY-PHOSPHORYL)-BUTYRIC ACID ETHYL ESTER;InChI=1/C10H21O5P/c1-5-9(10(11)13-6-2)16(12,14-7-3)15-8-4/h9H,5-8H2,1-4H3

Chemical Property of Triethyl 2-phosphonobutyrate

Chemical Property:

• Vapor Pressure: 0.000443mmHg at 25°C
• Refractive Index: n20/D 1.432(lit.)
• Boiling Point: 315.2°Cat760mmHg
• Flash Point: 158.3°C
• PSA: 71.64000
• Density: 1.076g/cm³
• LogP: 2.59420
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Not miscible or difficult to mix with water.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 252.11266076
• Heavy Atom Count: 16
• Complexity: 244

Purity/Quality:

98% min ^*data from raw suppliers

Triethyl 2-phosphonobutyrate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(C(=O)OCC)P(=O)(OCC)OCC
• Uses: Reactant used for preparation of furospinosulin-1 and analogs as hypoxia-selective antitumor agents, Aminoquinolines as beta-site amyloid precursor protein cleaving enzyme 1 (BACE1) inhibitors and potential anti-Alzheimer?s drugs, phenylpropanoic acid peroxisome proliferator-activated receptor (PPAR) α-selective agonists as nonalcoholic steatohepatitis (NASH)-preventive agents, PPAR agonists with phenethylphenylphthalimide skeleton derived from thalidomide-related LXR antagonists, notch-sparing γ-secretase inhibitors derived from PPAR agonist library and plakotenin via Diels-Alder reaction, as a potential anticancer agent, naturally found in Okinawan sponge of the genus Plakortis. Reactant for preparation of:Furospinosulin-1 and analogs as hypoxia-selective antitumor agentsAminoquinolines as beta-site amyloid precursor protein cleaving enzyme 1 (BACE1) inhibitors and potential anti-Alzheimer′s drugsPhenylpropanoic acid peroxisome proliferator-activated receptor (PPAR) α-selective agonists as nonalcoholic steatohepatitis (NASH)-preventive agentsPPAR agonists with phenethylphenylphthalimide skeleton derived from thalidomide-related LXR antagonistsNotch-sparing γ-secretase inhibitors derived from PPAR agonist libraryPlakotenin via Diels-Alder reaction, as a potential anticancer agent, naturally found in Okinawan sponge of the genus PlakortisQuinone/naphthoquinone-substituted propenoic acids as inhibitors of cell growth and redox function of apurinic/apyrimidinic endonuclease 1/redox enhancing factor 1 (Ape1/Ref-1)α-alkenyl cyclic ethers by asymmetric dehydrative cyclization of ω-hydroxy allyl alcohols catalyzed by Ru complexes of axially chiral naphthylpyridinecarboxylatesBranched phosphonoethoxyethyl purines as new acyclic nucleoside phosphonates which inhibit Plasmodium falciparum (malarial parasite) hypoxanthine-guanine-xanthine phosphoribosyltransferase (HGXPRT)Phenylpropanoic acid-type peroxisome proliferator-activated receptor pan agonists as candidate drugs for treatment of altered metabolic homeostasis

Technology Process of Triethyl 2-phosphonobutyrate

There total 16 articles about Triethyl 2-phosphonobutyrate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.55%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + ethyl iodide (75-03-6) → triethyl 2-ethylphosphonoacetate (17145-91-4)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With potassium tert-butylate; In dimethyl sulfoxide; at 0 ℃; for 0.5h;

ethyl iodide; In dimethyl sulfoxide; at 60 ℃; for 1.5h;

DOI:10.1021/acs.jmedchem.1c00621

Reference yield: 80.0%

ethyl bromide (74-96-4) + diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) → triethyl 2-ethylphosphonoacetate (17145-91-4)

Guidance literature:

With sodium hydride; In 1,2-dimethoxyethane; at 0 - 60 ℃; for 5h;

DOI:10.1021/acs.jcim.7b00733

Reference yield: 63.0%

triethyl phosphite (122-52-1) + 2-bromobutyric acid ethyl ester (533-68-6) → triethyl 2-ethylphosphonoacetate (17145-91-4)

Guidance literature:

at 155 ℃; for 20h;

DOI:10.1002/anie.201305218

upstream raw materials:

triethyl phosphite

2-bromobutyric acid ethyl ester

ethanol

C₆H₁₀Cl₃O₂P

Downstream raw materials:

2,4-Diaethyl-4-phenylbutadien-(2,3)-carbonsaeure-aethylester

1-aminopropanephosphonic acid

Ethyl 3-<(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyl-5-oxazolidinyl>-2-ethyl-2-propenoate

(E)-2-ethyl-3-[4-(pyridin-3-ylmethyl)phenyl]acrylic acid ethyl ester

Refernces

• 1、 Magalh?es, Joana,Annunziato, Giannamaria,Franko, Nina,Pieroni, Marco,Campanini, Barbara,Bruno, Agostino,Costantino, Gabriele. "Integration of Enhanced Sampling Methods with Saturation Transfer Difference Experiments to Identify Protein Druggable Pockets". . p. 710 - 723. Retrieved 2018/03/30.
• 2、 Lin, Luqing,Romano, Ciro,Mazet, Clément. "Palladium-Catalyzed Long-Range Deconjugative Isomerization of Highly Substituted α,β-Unsaturated Carbonyl Compounds". supporting information. p. 10344 - 10350. Retrieved 2016/08/31.