ethyl (2E)-2-(diethoxyphosphoryl)but-2-enoate

• ChemBase ID: 295184
• Molecular Formular: C10H19O5P
• Molecular Mass: 250.228621
• Monoisotopic Mass: 250.09701034
• SMILES: CCOC(=O)/C(=C\C)/P(=O)(OCC)OCC
• Canonical SMILES: CCOC(=O)/C(=C\C)/P(=O)(OCC)OCC
• InChI: InChI=1S/C10H19O5P/c1-5-9(10(11)13-6-2)16(12,14-7-3)15-8-4/h5H,6-8H2,1-4H3/b9-5+
• InChIKey: LKGVVQTVNFFWAT-WEVVVXLNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2E)-2-(diethoxyphosphoryl)but-2-enoate
• IUPAC Traditional name: ethyl (2E)-2-(diethoxyphosphoryl)but-2-enoate
• Synonyms: 4-Phosphonocrotonic acid triethyl ester; Triethyl trans-4-phosphono-2-butenoate; Triethyl 4-phosphonocrotonate, cis + trans; 4-膦酰巴豆酸三乙酯, 顺式 + 反式

Database IDs

• CAS Number: 10236-14-3
• MDL Number: MFCD00009192
• PubChem SID: 180680715
• PubChem CID: 6272114

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.7304593
• LogD (pH = 7.4): 1.7304593
• Log P: 1.7304593
• Molar Refractivity: 62.1999 cm^3
• Polarizability: 24.433794 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 133-135°C/0.4mm
• Flash Point: >110°C(230°F)
• Density: 1.130
• Refractive Index: 1.4550

Safety Information

• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 94%

REFERENCES

• Wadsworth-Emmons reaction with carbonyl compounds leads to conjugated dienoic esters. Use of LiHMDS or LDA as base results in a high proportion of the (E,E)-isomer: J. Am. Chem. Soc., 100, 3599 (1978).