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Methyltriphenylphosphonium iodide

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Methyltriphenylphosphonium iodide Basic information

Product Name:
Methyltriphenylphosphonium iodide
Synonyms:
  • METHYLTRIPHENYLPHOSPHONIUM IODIDE
  • MPJ
  • TRIPHENYLMETHYL PHOSPHONIUM IODIDE
  • Methyl triphenylphosphonium iodide, 98+%
  • METHYLTRIPHENYPHOSPHONIUMIODIDE
  • Methyltriphenylphosphanium iodide
  • Phosphonium, methyltriphenyl-, iodide
  • Triphenylmethylphosphine iodide
CAS:
2065-66-9
MF:
C19H18IP
MW:
404.22
EINECS:
218-178-5
Product Categories:
  • C-C Bond Formation
  • Olefination
  • Wittig Reagents
  • Phosphonium Compounds
  • Synthetic Organic Chemistry
  • Wittig & Horner-Emmons Reaction
  • Wittig Reaction
Mol File:
2065-66-9.mol
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Methyltriphenylphosphonium iodide Chemical Properties

Melting point:
183-185 °C(lit.)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Powder
color 
White to light yellow
Water Solubility 
SOLUBLE
Sensitive 
Light Sensitive & Hygroscopic
InChI
InChI=1S/C19H18P.HI/c1-20(17-11-5-2-6-12-17,18-13-7-3-8-14-18)19-15-9-4-10-16-19;/h2-16H,1H3;1H/q+1;/p-1
InChIKey
JNMIXMFEVJHFNY-UHFFFAOYSA-M
SMILES
[P+](C)(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[I-]
CAS DataBase Reference
2065-66-9(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi,T
Risk Statements 
36/37/38-25
Safety Statements 
26-36-45-37/39-28A
RIDADR 
UN3464
WGK Germany 
3
HazardClass 
6.1
PackingGroup 
III
HS Code 
29319090

MSDS

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Methyltriphenylphosphonium iodide Usage And Synthesis

Chemical Properties

WHITE TO LIGHT YELLOW POWDER

Uses

suzuki reaction

Uses

Methyltriphenylphosphonium iodide is as a reactant for synthesis of triphenylamine-based dyes and polyolefinic aromatic molecules with pyrene for use in dye-sensitized solar cells. Used as ligand in coupling reaction. It is also used as a precursor to a Wittig reagent.

Preparation

Methyltriphenylphosphonium iodide was prepared by the following procedure. Triphenylphosphine was recrystallized from ethanol and dried over phosphorus pentoxide under reduced pressure for 12 hr. A solution of 39 g (0.15 mol) of triphenylphosphine and 10.0 mL (22.8 g, 0.16 mol) of iodomethane in 105 mL of benzene was allowed to stir at room temperature for 12 hr. The precipitate was filtered, washed with benzene, and dried over phosphorus pentoxide under reduced pressure for 12 hr. The yield was 57 g (94%), mp 189°C (lit.2 mp 182°C).

reaction suitability

reaction type: C-C Bond Formation

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