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Merck
CN

330671

Sigma-Aldrich

2-(Trimethylsilyl)ethoxymethyl-triphenylphosphonium chloride

98%

Synonym(s):

SEM-triphenylphosphonium chloride

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About This Item

Linear Formula:
(CH3)3SiCH2CH2OCH2P(C6H5)3Cl
CAS Number:
Molecular Weight:
429.01
Beilstein:
4632507
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22
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Assay

98%

reaction suitability

reaction type: C-C Bond Formation

mp

145-149 °C (lit.)

functional group

ether
phosphine

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

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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

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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