ethyl 4-(diethoxyphosphoryl)but-2-enoate

• ChemBase ID: 7543
• Molecular Formular: C10H19O5P
• Molecular Mass: 250.228621
• Monoisotopic Mass: 250.09701034
• SMILES: O=C(OCC)/C=C/CP(=O)(OCC)OCC
• Canonical SMILES: CCOC(=O)/C=C/CP(=O)(OCC)OCC
• InChI: InChI=1S/C10H19O5P/c1-4-13-10(11)8-7-9-16(12,14-5-2)15-6-3/h7-8H,4-6,9H2,1-3H3/b8-7+
• InChIKey: LXLODBXSCRTXFG-BQYQJAHWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 4-(diethoxyphosphoryl)but-2-enoate; ethyl (2E)-4-(diethoxyphosphoryl)but-2-enoate
• IUPAC Traditional name: ethyl 4-(diethoxyphosphoryl)but-2-enoate; ethyl (2E)-4-(diethoxyphosphoryl)but-2-enoate
• Synonyms: Ethyl (2E)-4-(diethoxyphosphoryl)but-2-enoate; Ethyl trans-4-(diethylphosphono)crotonate; Ethyl trans-4-(diethoxyphosphoryl)crotonate; Ethyl 4-(diethoxyphosphoryl)but-2-enoate; Ethyl 4-(diethylphosphono)crotonate; Ethyl 4-(diethoxyphosphoryl)crotonate; Triethyl 4-phosphonocrotonate; 4-(Diethoxyphosphinyl)-2-butenoic acid ethyl ester; 4-Phosphonocrotonic acid triethyl ester; Triethyl 4-phosphonocrotonate, mixture of isomers; 4-膦酰丁烯酸三乙酯，异构体混合物

Database IDs

• CAS Number: 10236-14-3
• MDL Number: MFCD00009192
• PubChem SID: 24847263; 160970850
• PubChem CID: 5365783

CALCULATED PROPERTIES

• H Donor: 0
• LogD (pH = 5.5): 1.6964072
• LogD (pH = 7.4): 1.6964072
• Log P: 1.6964072
• Molar Refractivity: 61.7596 cm^3
• Polarizability: 24.433794 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true
• H Acceptors: 2

PROPERTIES

Physical Property

• Boiling Point: 133-135°C/0.4mm; 135 °C/0.4 mmHg(lit.)
• Flash Point: 113 °C; 113°C; 235.4 °F
• Density: 1.128; 1.128 g/mL at 25 °C(lit.)
• Refractive Index: 1.4550; n20/D 1.455(lit.)

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37/39
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: 90%; 90+%
• Grade: technical grade
• Linear Formula: (C2H5O)2P(O)CH2CH=CHCO2C2H5

DETAILS

Apollo Scientific Ltd - OR42028

Mixture of cis/trans isomers

Sigma Aldrich - 116092

Packaging
10 g in glass bottle
Application
Reactant for:
• Iminodipropionic acid as a leaving group for DNA polymerization by HIV-1 reverse transcriptase1
• Stereoselective preparation of C1-C19 fragment of macrolide antibiotic aplyronine A using diastereoselective Nozaki-Hiyama-Kishi coupling reactions2
• Orally bioavailable GPR40 agonist synthesis3
• Synthesis of fluoroketone inhibitors of group VIA calcium-independent phospholipase A24
• Preaparation of mGlu4R agonists5
• Dearomatizing cyclization of nicotinyl-substituted esters and ketones6