(2-ethoxy-2-oxoethyl)triphenylphosphanium chloride

• ChemBase ID: 74862
• Molecular Formular: C22H22ClO2P
• Molecular Mass: 384.835641
• Monoisotopic Mass: 384.10459425
• SMILES: [P+](c1ccccc1)(c1ccccc1)(c1ccccc1)CC(=O)OCC.[Cl-]
• Canonical SMILES: CCOC(=O)C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Cl-]
• InChI: InChI=1S/C22H22O2P.ClH/c1-2-24-22(23)18-25(19-12-6-3-7-13-19,20-14-8-4-9-15-20)21-16-10-5-11-17-21;/h3-17H,2,18H2,1H3;1H/q+1;/p-1
• InChIKey: DJGHVEPNEJKZBF-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-ethoxy-2-oxoethyl)triphenylphosphanium chloride
• IUPAC Traditional name: (2-ethoxy-2-oxoethyl)triphenylphosphanium chloride
• Synonyms: (Carboethoxymethyl)triphenylphosphonium chloride; Ethyl (triphenylphosphonio)acetate chloride; (Ethoxycarbonylmethyl)triphenylphosphonium chloride; (2-Ethoxy-2-oxoethyl)triphenylphosphonium chloride; (Ethoxycarbonylmethyl)triphenylphosphonium chloride; (乙氧基羰基甲基)三苯基氯化膦

Database IDs

• CAS Number: 17577-28-5
• EC Number: 241-548-2
• MDL Number: MFCD00011746
• Beilstein Number: 3924139
• PubChem SID: 24845340; 162039780
• PubChem CID: 87159

CALCULATED PROPERTIES

• Acid pKa: 19.34738
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 4.4009204
• LogD (pH = 7.4): 4.4009204
• Log P: 4.4009204
• Molar Refractivity: 102.9219 cm^3
• Polarizability: 40.63268 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 120-123 °C (dec.); 120-123 °C(lit.); ca 145°C dec.

Safety Information

• Storage Warning: Hygroscopic; Irritant/Hygroscopic/Store at 2-8°C
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (AT); 97%
• Grade: technical
• Linear Formula: CH3CH2OCOCH2P(Cl)(C6H5)3

DETAILS

Sigma Aldrich - 02615

Other Notes
Starting material for preparing the Wittig-reagent6,7,8
Application
Reactant for:
• Preparation of disubstituted tetrahydrofurans as selective serotonin re-uptake inhibitors for the treatment of depression1
• Ring-opening reactions with Wittig reagents2
• Enantioselective total synthesis of the phytotoxic lactone herbarumin III via Keck′s asymmetric allylation and Sharpless epoxidation3
• Synthesis of fluorobenzofurans via microwave-assisted tandem intramolecular Wittig and Claisen rearrangement reactions4
• Preparation of phosphonium derivatives of coumarin5