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2,4,6-Trimethyliodobenzene

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2,4,6-Trimethyliodobenzene Basic information

Product Name:
2,4,6-Trimethyliodobenzene
Synonyms:
  • Iodomesitylene~2,4,6-Trimethyliodobenzene
  • 2,4,6-TRIMETHYLIODOBENZENE (2-IODOMESITYLENE)
  • 2,4,6-Trimethylphenyl iodide
  • Mesityliodine
  • 2,4,6-Trimethyliodobenzene,98%
  • 2-Iodo-3-isopropyltoluene
  • 2,4,6-Trimethyliodobenzene 98%
  • 2-Iodo-1,3,5-trimethylbenzene, 2-Iodomesitylene, Mesityl iodide
CAS:
4028-63-1
MF:
C9H11I
MW:
246.09
EINECS:
223-709-9
Product Categories:
  • Aromatic Halides (substituted)
Mol File:
4028-63-1.mol
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2,4,6-Trimethyliodobenzene Chemical Properties

Melting point:
28-32 °C
Boiling point:
250 °C
Density 
1.5100 (rough estimate)
refractive index 
1.5905 (estimate)
storage temp. 
2-8°C(protect from light)
form 
powder to lump to clear liquid
color 
White or Colorless to Light yellow
Sensitive 
Light Sensitive
BRN 
1860064
InChIKey
GTPNXFKONRIHRW-UHFFFAOYSA-N
CAS DataBase Reference
4028-63-1(CAS DataBase Reference)
NIST Chemistry Reference
2,4,6-Trimethyliodobenzene(4028-63-1)
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Safety Information

Risk Statements 
36/37/38
Safety Statements 
24/25-36/37/39-24/28
HazardClass 
LIGHT SENSITIVE
HS Code 
29039990

MSDS

  • Language:English Provider:ACROS
  • Language:English Provider:ALFA
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2,4,6-Trimethyliodobenzene Usage And Synthesis

Chemical Properties

yellow crystalline low melting solid

Uses

suzuki reaction

Uses

Iodomesitylene can be used as a good catalyst for living radical polymerization due to its good molecular weight distribution.

Synthesis Reference(s)

Tetrahedron Letters, 10, p. 2427, 1969 DOI: 10.1017/S0009838800024678

Hazard

May cause eye, skin, and respiratory tract irritation. Light sensitive.

Health effects

Eye: May cause eye irritation.
Skin: May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion: May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation: May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.

Synthesis

The synthesis of 2,4,6-Trimethyliodobenzene is as follows:
A 10 mL glass flask equipped with a magnetic stir bar wascharged with a methyl ketone (1 mmol) and dissolved in MeCN (2 mL). To thermostat solution NH4NO3 (10-25 mol%), I2 (50 mol%) and H2SO4 (aqueous 96% solution, 10-20 mol%) were added and the flask was furtherequipped with a balloon filled with air (1 L) and magnetically stirred at 60 C.The consumption of starting material was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature, diluted withEtOAc (10 mL), and insoluble material identified as ammonium sulfate filtered off. The filtrate neutralized with NaHCO3 (aqueous 10% solution, 2 mL)and Na2S2O3 (aqueous 10% solution, 2 mL) and phase was separated. The waterphase was washed with EtOAc additionally two times (2 5 mL). The combined organic phase was dried over anhydrous Na2SO4 and the solvent distilled under reduced pressure. The crude product obtained was analyzed by 1H NMR. Finally, the crude product was purified using column chromatography (SiO2, n-hexane/CH2Cl2 elution) and preparative thin layer chromatography to afford purematerial.

storage

Store in a cool, dry place. Store in a tightly closed container. Store protected from light.

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