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330671 Sigma-Aldrich

2-(Trimethylsilyl)ethoxymethyl-triphenylphosphonium chloride

98%

Synonym: SEM-triphenylphosphonium chloride

  • CAS Number 82495-75-8

  • Linear Formula (CH3)3SiCH2CH2OCH2P(C6H5)3Cl

  • Molecular Weight 429.01

  •  Beilstein/REAXYS Number 4632507

  •  MDL number MFCD00043159

  •  PubChem Substance ID 24859880

  •  NACRES NA.22

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Properties

Related Categories C-C Bond Formation, Chemical Synthesis, Olefination, Synthetic Reagents, Wittig Reagents More...
Quality Level   100
assay   98%
reaction suitability   reaction type: C-C Bond Formation
mp   145-149 °C (lit.)
storage temp.   room temp
SMILES string   [Cl-].C[Si](C)(C)CCOC[P+](c1ccccc1)(c2ccccc2)c3ccccc3
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
InChI key   NEUMNYXEDIPGJD-UHFFFAOYSA-M

Description

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 interaction
• Preparation of aliphatic and alicyclic aldehydes by homologation of aldehydes
• Wittig reactions
• Preparation of optically active (1S,5R)-(+)-3-azabicyclo[3.2.2]non-6-en-2-one via enantioselective intramolecular cyclopropanation

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles
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