ethyl 4-(diethoxyphosphoryl)-3-methylbut-2-enoate

• ChemBase ID: 75013
• Molecular Formular: C11H21O5P
• Molecular Mass: 264.255201
• Monoisotopic Mass: 264.1126604
• SMILES: P(=O)(OCC)(OCC)C/C(=C/C(=O)OCC)/C
• Canonical SMILES: CCOC(=O)/C=C(/CP(=O)(OCC)OCC)\C
• InChI: InChI=1S/C11H21O5P/c1-5-14-11(12)8-10(4)9-17(13,15-6-2)16-7-3/h8H,5-7,9H2,1-4H3
• InChIKey: OQKGPUSERILONW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 4-(diethoxyphosphoryl)-3-methylbut-2-enoate; ethyl (2E)-4-(diethoxyphosphoryl)-3-methylbut-2-enoate
• IUPAC Traditional name: ethyl 4-(diethoxyphosphoryl)-3-methylbut-2-enoate; ethyl (2E)-4-(diethoxyphosphoryl)-3-methylbut-2-enoate
• Synonyms: Ethyl 4-(diethoxyphosphoryl)-3-methylbut-2-enoate; Diethyl [3-(ethoxycarbonyl)-2-methylprop-2-en-1-yl]phosphonate; Ethyl 4-(diethoxyphosphoryl)-3-methylcrotonate, tech; Diethyl 3-ethoxycarbonyl-2-methyl-2-propenyl phosphonate; Triethyl 3-methyl-4-phosphonocrotonate; Triethyl 4-phosphonosenecioate, mixture of cis and trans; Triethyl 3-methyl-4-phosphono-2-butenoate, mixture of cis and trans; Triethyl 4-phosphonosenecioate; Triethyl 3-methyl-4-phosphono-2-butenoate; Triethyl (2E)-3-Methyl-4-phosphono-2-butenoate; (2E)-4-(Diethoxyphosphinyl)-3-methyl-2-butenoic Acid Ethyl Ester; Diethyl [(E)-3-(Ethoxycarbonyl)-2-methylallyl]phosphonate; Triethyl (2E)-3-Methyl-4-phosphonocrotonate; 4-膦酰基千里酸三乙酯，顺式和反式混合物; 3-甲基-4-膦酰基-2-丁烯酸三乙酯，顺式和反式混合物; 4-膦酰基千里酸三乙酯; 3-甲基-4-膦酰基-2-丁烯酸三乙酯

Database IDs

• CAS Number: 41891-54-7
• MDL Number: MFCD00075151; MFCD08445507
• Beilstein Number: 2417880
• PubChem SID: 24860594; 162039931; 24885847
• PubChem CID: 6000084

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.9310948
• LogD (pH = 7.4): 1.9310948
• Log P: 1.9310948
• Molar Refractivity: 66.0416 cm^3
• Polarizability: 26.25924 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Yellow Oil
• Boiling Point: 284-287 °C(lit.); 284-287°C
• Flash Point: 113 °C; 113°C; 235.4 °F
• Density: 1.07 g/mL at 20 °C(lit.); 1.089; 1.089 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.46; n20/D 1.46(lit.)

Safety Information

• Storage Condition: -86°C Freezer, Under Inert Atmosphere
• Storage Warning: Irritant
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: 2-8°C

Product Information

• Purity: ~85% (GC); 80%
• Grade: technical; technical grade
• Linear Formula: (C2H5O)2P(O)CH2C(CH3)=CHCO2C2H5
• Empirical Formula (Hill Notation): C11H21O5P

DETAILS

Apollo Scientific Ltd - OR10804

Mixture of cis/trans isomers

Sigma Aldrich - 338958

Packaging
5 g in glass bottle
Application
Reactant for preparation of:
• Bicyclodecenes and oxabicyclodecenes via intramolecular [4 + 3]-cycloaddition, using alkylation, olefination and coupling1
• Methyloctatrienoic acid retinoid X receptor modulators from insulin sensitizers for the treatment of type II diabetes2

Sigma Aldrich - 68760

Other Notes
Wittig reagent used for the synthesis of terpenes and other polyunsaturated esters1