ethyl 2-(diethoxyphosphoryl)butanoate

• ChemBase ID: 151456
• Molecular Formular: C10H21O5P
• Molecular Mass: 252.244501
• Monoisotopic Mass: 252.1126604
• SMILES: CCC(C(=O)OCC)P(=O)(OCC)OCC
• Canonical SMILES: CCOC(=O)C(P(=O)(OCC)OCC)CC
• InChI: InChI=1S/C10H21O5P/c1-5-9(10(11)13-6-2)16(12,14-7-3)15-8-4/h9H,5-8H2,1-4H3
• InChIKey: GYUCVQSNZFRDRL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-(diethoxyphosphoryl)butanoate
• IUPAC Traditional name: ethyl 2-(diethoxyphosphoryl)butanoate
• Synonyms: α-Diethylphosphonobutanoic acid ethyl ester; Ethyl 2-(diethoxyphosphoryl)butanoate; NSC 22423; Triethyl 2-phosphonobutyrate; Diethyl 1-(ethoxycarbonyl)propanephosphonate; 2-Phosphonobutyric acid triethyl ester; 2-膦酰丁酸三乙酯; 2-膦酰丁酸三乙脂

Database IDs

• CAS Number: 17145-91-4
• MDL Number: MFCD00041347
• Beilstein Number: 1789280
• PubChem SID: 162245609; 24866152
• PubChem CID: 229053

CALCULATED PROPERTIES

• Acid pKa: 19.14348
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.6442976
• LogD (pH = 7.4): 1.6442976
• Log P: 1.6442976
• Molar Refractivity: 60.6314 cm^3
• Polarizability: 24.684145 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 105-106°C/2mm; 152-154 °C/14 mmHg(lit.)
• Flash Point: >110°C(230°F); 113 °C; 235.4 °F
• Density: 1.064; 1.064 g/mL at 25 °C(lit.)
• Refractive Index: 1.4330; n20/D 1.432(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; 36/38
• Safety Statements: 23-26-37; 26-36
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P305+P351+P338-P302+P352-P321-P362-P332+P313
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: 97%; 98%
• Linear Formula: (C2H5O)2P(O)CH(C2H5)CO2C2H5

DETAILS

Sigma Aldrich - 417467

Packaging
5, 25 mL in glass bottle
Application
Reactant for preparation of:
• Furospinosulin-1 and analogs as hypoxia-selective antitumor agents1
• Aminoquinolines as beta-site amyloid precursor protein cleaving enzyme 1 (BACE1) inhibitors and potential anti-Alzheimer′s drugs2
• Phenylpropanoic acid peroxisome proliferator-activated receptor (PPAR) α-selective agonists as nonalcoholic steatohepatitis (NASH)-preventive agents3
• PPAR agonists with phenethylphenylphthalimide skeleton derived from thalidomide-related LXR antagonists4
• Notch-sparing γ-secretase inhibitors derived from PPAR agonist library5
• Plakotenin via Diels-Alder reaction, as a potential anticancer agent, naturally found in Okinawan sponge of the genus Plakortis6
• Quinone/naphthoquinone-substituted propenoic acids as inhibitors of cell growth and redox function of apurinic/apyrimidinic endonuclease 1/redox enhancing factor 1 (Ape1/Ref-1)7
• α-alkenyl cyclic ethers by asymmetric dehydrative cyclization of ω-hydroxy allyl alcohols catalyzed by Ru complexes of axially chiral naphthylpyridinecarboxylates8
• Branched phosphonoethoxyethyl purines as new acyclic nucleoside phosphonates which inhibit Plasmodium falciparum (malarial parasite) hypoxanthine-guanine-xanthine phosphoribosyltransferase (HGXPRT)9
• Phenylpropanoic acid-type peroxisome proliferator-activated receptor pan agonists as candidate drugs for treatment of altered metabolic homeostasis10

REFERENCES

• Intermediate for Wadsworth-Emmons formation of ɑ-ethylacrylic esters. See Appendix 1.