diethyl [(2E)-but-2-en-1-yl]phosphonate

• ChemBase ID: 142851
• Molecular Formular: C8H17O3P
• Molecular Mass: 192.192541
• Monoisotopic Mass: 192.09153103
• SMILES: CCOP(=O)(C/C=C/C)OCC
• Canonical SMILES: CCOP(=O)(C/C=C/C)OCC
• InChI: InChI=1S/C8H17O3P/c1-4-7-8-12(9,10-5-2)11-6-3/h4,7H,5-6,8H2,1-3H3/b7-4+
• InChIKey: KGWLPYVMUWAOJC-QPJJXVBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl [(2E)-but-2-en-1-yl]phosphonate
• IUPAC Traditional name: diethyl (2E)-but-2-en-1-ylphosphonate
• Synonyms: Diethyl trans-crotyl phosphonate; Diethyl 2-butenylphosphonate, predominantly trans; 反式-巴豆基膦酸二乙酯; 2-丁烯基膦酸二乙酯，主要为反式

Database IDs

• CAS Number: 682-34-8
• MDL Number: MFCD05865177
• PubChem SID: 162237077; 24881705
• PubChem CID: 10943314

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.7245853
• LogD (pH = 7.4): 1.7245853
• Log P: 1.7245853
• Molar Refractivity: 50.5998 cm^3
• Polarizability: 19.91325 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Density: 1.014 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.4400(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37
• 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: 95%
• Linear Formula: H3CCH=CHCH2PO(OCH2CH3)2

DETAILS

Sigma Aldrich - 597597

Packaging
1, 5 g in glass bottle
Application
Olefinic partner for Pauson-Khand reaction with alkyne cobalt complex1Reactant for:
• Synthesis of di-Et 1-substituted vinylphosphonates via decarboxylative condensation2
• Sequential lithiation and silylation3
• Palladium catalyzed allylic acetoxylation4
• Preparation of building blocks of retinoid chemistry5