diethyl (but-3-en-1-yl)phosphonate

• ChemBase ID: 141897
• Molecular Formular: C8H17O3P
• Molecular Mass: 192.192541
• Monoisotopic Mass: 192.09153103
• SMILES: CCOP(=O)(CCC=C)OCC
• Canonical SMILES: CCOP(=O)(OCC)CCC=C
• InChI: InChI=1S/C8H17O3P/c1-4-7-8-12(9,10-5-2)11-6-3/h4H,1,5-8H2,2-3H3
• InChIKey: NUDGAPYPOAQVLP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl (but-3-en-1-yl)phosphonate
• IUPAC Traditional name: diethyl but-3-en-1-ylphosphonate
• Synonyms: P-3-Buten-1-yl-phosphonic acid diethyl ester; Diethyl 3-butenylphosphonate; 3-丁烯基磷羧酸乙酯

Database IDs

• CAS Number: 15916-48-0
• MDL Number: MFCD06200726
• PubChem SID: 162236130; 24883099
• PubChem CID: 10997850

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.6189991
• LogD (pH = 7.4): 1.6189991
• Log P: 1.6189991
• Molar Refractivity: 49.6813 cm^3
• Polarizability: 19.91325 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 55 °C/0.55 mmHg(lit.)
• Flash Point: 105 °C; 221 °F
• Density: 1.005 g/mL at 25 °C(lit.)

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2810
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2810 6.1/PG 3

Product Information

• Purity: 95%
• Linear Formula: CH2=CHCH2CH2PO(OCH2CH3)2

DETAILS

Sigma Aldrich - 640522

Packaging
1, 10 g in glass bottle
Application
Reactant for synthesis of:
• Bicyclo[3.3.1]alkenone framework compounds by gold-catalyzed Diels-Alder reactions1
• Antiviral C-5-substituted pyrimidine acyclic nucleoside phosphonates selected as human thymidylate kinase substrates2
• Antimalarials via halogenation of di-Et butenylphosphonate3
• Bisphosphonate enynes4Reactant for:
• Remote supramolecular control of catalyst selectivity in hydroformlyation of alkenes5
• Intermolecular metal-catalyzed carbenoid cyclopropanations6
• Chemoenzymatic synthesis of phosphic derivatives of carbohydrates7