triphenyl({[2-(trimethylsilyl)ethoxy]methyl})phosphanium chloride

• ChemBase ID: 147680
• Molecular Formular: C24H30ClOPSi
• Molecular Mass: 429.006661
• Monoisotopic Mass: 428.14920642
• SMILES: C[Si](C)(C)CCOC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Cl-]
• Canonical SMILES: C[Si](CCOC[P+](c1ccccc1)(c1ccccc1)c1ccccc1)(C)C.[Cl-]
• InChI: InChI=1S/C24H30OPSi.ClH/c1-27(2,3)20-19-25-21-26(22-13-7-4-8-14-22,23-15-9-5-10-16-23)24-17-11-6-12-18-24;/h4-18H,19-21H2,1-3H3;1H/q+1;/p-1
• InChIKey: NEUMNYXEDIPGJD-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: triphenyl({[2-(trimethylsilyl)ethoxy]methyl})phosphanium chloride
• IUPAC Traditional name: triphenyl({[2-(trimethylsilyl)ethoxy]methyl})phosphanium chloride
• Synonyms: SEM-triphenylphosphonium chloride; 2-(Trimethylsilyl)ethoxymethyl-triphenylphosphonium chloride; SEM-三苯基氯化磷; 2-(三甲基硅烷)乙氧三苯甲基氯化膦

Database IDs

• CAS Number: 82495-75-8
• MDL Number: MFCD00043159
• Beilstein Number: 4632507
• PubChem SID: 162241867; 24889705; 24859880
• PubChem CID: 11396265

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 7.1083
• LogD (pH = 7.4): 7.1083
• Log P: 7.1083
• Molar Refractivity: 113.79 cm^3
• Polarizability: 47.208263 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 145-149 °C(lit.); 166-169 °C

Safety Information

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

Product Information

• Purity: ≥97.0% (AT); 98%
• Grade: purum
• Linear Formula: (CH3)3SiCH2CH2OCH2P(C6H5)3Cl

DETAILS

Sigma Aldrich - 330671

Packaging
1, 5 g in glass bottle
Application
Reactant for:
• Enantioselective synthesis of (-)-sarain A using asymmetric Michael addition, cyclization, ring-closing metathesis, intramolecular Stille coupling, and late-state installation of tertiary amine-aldehyde proximity interaction1
• Preparation of aliphatic and alicyclic aldehydes by homologation of aldehydes2
• Wittig reactions3
• Preparation of optically active (1S,5R)-(+)-3-azabicyclo[3.2.2]non-6-en-2-one via enantioselective intramolecular cyclopropanation4

Sigma Aldrich - 92742

Other Notes
For the preparation of 2-(trimethylsilyl)ethyl protected dienol ethers which may undergo intramolecular Diels-Alder reactions5; Homologation of carbonyl compounds6,7
Application
Reactant for:
• Enantioselective synthesis of (-)-sarain A using asymmetric Michael addition, cyclization, ring-closing metathesis, intramolecular Stille coupling, and late-state installation of tertiary amine-aldehyde proximity interaction1
• Preparation of aliphatic and alicyclic aldehydes by homologation of aldehydes2
• Wittig reactions3
• Preparation of optically active (1S,5R)-(+)-3-azabicyclo[3.2.2]non-6-en-2-one via enantioselective intramolecular cyclopropanation4