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CAS RN: 33035-41-5 | Product Number: I0479

Iodomesitylene Diacetate


Purity: >98.0%(T)
Synonyms:
  • 2-(Diacetoxyiodo)mesitylene
  • 2,4,6-Trimethyl(diacetoxyiodo)benzene
  • 2,4,6-Trimethyliodobenzene Diacetate
Documents:
5G
£38.00
7   ≥20 
25G
£114.00
2   ≥20 

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Product Number I0479
Purity / Analysis Method >98.0%(T)
Molecular Formula / Molecular Weight C__1__3H__1__7IO__4 = 364.18  
Physical State (20 deg.C) Solid
Storage Temperature 0-10°C
Condition to Avoid Heat Sensitive
CAS RN 33035-41-5
Reaxys Registry Number 2508343
PubChem Substance ID 87571828
SDBS (AIST Spectral DB) 19670
MDL Number

MFCD00674196

Specifications
Appearance White to Light yellow powder to crystal
Purity(Iodometric Titration) min. 98.0 %
Solubility in Methanol almost transparency
Properties (reference)
Melting Point 168 °C
Solubility (soluble in) Methanol
GHS
Pictogram Pictogram
Signal Word Warning
Hazard Statements H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
Precautionary Statements P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P302 + P352 : IF ON SKIN: Wash with plenty of water.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P362 + P364 : Take off contaminated clothing and wash it before reuse.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
Related Laws:
Transport Information:
HS Number 2931900090
Application
Copper/photoredox-catalyzed Decarbonylative sp3 C–N Coupling Reaction of N-Heteroaromatics

Preparation of Iodomesitylene Dicarboxylates: Iodomesitylene diacetate (10 mmol), cyclohexyl carboxylic acid (20.5 mmol), and toluene (200 mL) are placed in flask. The solvent is removed by a rotary evaporator at 55 °C. This step is repeated with toluene (100 mL) as needed. The residue is concentrated in vacuo, to provide iodomesitylene dicarboxylates that can be directly used in the decarboxylative sp3 C–N coupling reactions without further purification.

sp3 C–N Coupling Reaction: Ir(F-Meppy)2(dtbbpy)PF6 (4.9 mg, 5.0 µmol), copper(I) 2-Thiophenecarboxylate (19 mg, 0.10 mmol), bathophenanthroline (50 mg, 0.15 mmol), 2-tert-butyl-1,1,3,3-tetramethylguanidine (0.21 mL, 171 mg, 1.0 mmol), 3-chloro-1H-indazole (76 mg, 0.50 mmol), iodomesitylene dicyclohexanecarboxylate (500 mg, 1.0 mmol), and 1,4-dioxane(12 mL) is placed in vial. The solution is sonicated until it becomes homogeneous and is then degassed with nitrogen. The reaction is stirred and irradiated using two 34-W blue LED lamps for 1 h. After the reaction has completed, the reaction mixture is diluted with water and EtOAc. The aqueous layer is extracted with EtOAc. The combined organic layers are washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue is purified by flash chromatography (30:1 hexane/EtOAc) on silica gel to afford the title compound (99 mg, 84% yield, >20:1 r.r.) as a colorless oil.

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