1-Iodo-3,5-dimethylbenzene

1-Iodo-3,5-dimethylbenzene Basic information
Product Name:1-Iodo-3,5-dimethylbenzene
Synonyms:3,5-dimethylphenyl iodide;1,3-DIMETHYL-5-IODOBENZENE;1-IODO-3,5-DIMETHYLBENZENE;3,5-DIMETHYLIODOBENZENE;5-IODO-M-XYLENE;5-Iodo-m-xylene (stabilized with Copper chip);5-Iodo-m-xylene,99%;Benzene, 1-Iodo-3,5-dimethyl-
CAS:22445-41-6
MF:C8H9I
MW:232.06
EINECS:629-121-2
Product Categories:Aromatic Hydrocarbons (substituted) & Derivatives;Halogen toluene;Iodine Compounds
Mol File:22445-41-6.mol
1-Iodo-3,5-dimethylbenzene Structure
1-Iodo-3,5-dimethylbenzene Chemical Properties
Melting point -2.9°C (estimate)
Boiling point 92-94 °C3 mm Hg(lit.)
density 1.608 g/mL at 25 °C(lit.)
refractive index n20/D 1.594(lit.)
Fp >230 °F
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Sparingly soluble (0.014 g/L) (25°C), Calc.
form Liquid
Specific Gravity1.608
color Clear light yellow
Sensitive Light Sensitive
BRN 2039353
InChIKeyZLMKEENUYIUKKC-UHFFFAOYSA-N
CAS DataBase Reference22445-41-6(CAS DataBase Reference)
NIST Chemistry ReferenceBenzene, 1-iodo-3,5-dimethyl-(22445-41-6)
Safety Information
Hazard Codes Xi,C
Risk Statements 36/37/38
Safety Statements 26-36-37/39
WGK Germany 3
Hazard Note Irritant
HS Code 29039990
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
1-Iodo-3,5-dimethylbenzene Usage And Synthesis
Chemical Propertiesclear light yellow liquid
Usessuzuki reaction
Uses1-Iodo-3,5-dimethylbenzene (5-iodo-m-xylene) is suitable for use in the synthesis of N-(3,5-xylyl)-N-ethyl aniline, an aryl amine, It is also used in the following studies; α-Arylation of ketones, Copper-catalyzed N-arylation of imidazoles, Cyanation of 5-iodo-m-xylene to form 3,5-dimethylbenzonitrile, synthesis of 1,3-Dimethyl-5-phenoxybenzene by nano-CuFe2O4 catalyzed C-O cross-coupling with phenol, CuBr-catalyzed amination of 1-iodo-3,5-dimethylbenzene to form N-Allyl-3,5-dimethylbenzenamine, copper-catalyzed C-S bond-formation between 5-iodo-m-xylene and thiophenol. It is also employed as a starting material in the synthesis of biphenyl-3,3?,5,5?-tetracarboxylic acid, radical bromination of 5-iodo-m-xylene by N-bromosuccinimide to form 1,3-bis(bromomethyl)-5-iodobenzene.
Uses1-Iodo-3,5-dimethylbenzene (5-iodo-m-xylene) is suitable for use in the synthesis of N-(3,5-xylyl)-N-ethylaniline, an arylamine.
It may be used in the following studies:
  • α-Arylation of ketones.
  • Copper-catalyzed N-arylation of imidazoles.
  • Cyanation of 5-iodo-m-xylene to form 3,5-dimethylbenzonitrile.
  • Synthesis of 1,3-Dimethyl-5-phenoxybenzene by nano-CuFe2O4 catalyzed C-O cross-coupling with phenol.
  • CuBr-catalyzed amination of 1-iodo-3,5-dimethylbenzene to form N-Allyl-3,5-dimethylbenzenamine.
  • Copper-catalyzed C-S bond-formation between 5-iodo-m-xylene and thiophenol.
  • As a starting material in the synthesis of biphenyl-3,3′,5,5′-tetracarboxylic acid.
  • Radical bromination of 5-iodo-m-xylene by N-bromosuccinimide to form 1,3-bis(bromomethyl)-5-iodobenzene.
General Description1-Iodo-3,5-dimethylbenzene (5-Iodo-m-xylene) is an aryl halide. It can be obtained from 5-bromo-m-xylene, via copper-catalyzed halogen exchange reaction, in the presence of NaI or KI in n-BuOH or DMF (solvents). It undergoes reaction with phenol in the presence of CuFe2O4 nano powder as a recyclable catalyst to afford 1,3-dimethyl-5-phenoxybenzene.
Xylene 1,4-Diiodobenzene 3,5-BIS(TRIFLUOROMETHYL)IODOBENZENE 1-Iodo-3,5-dimethylbenzene 3,5-BIS(1,1,1,3,3,3-HEXAFLUORO-2-HYDROXYPROPYL)IODOBENZENE DIMETHYL 5-IODOISOPHTHALATE Poly(dimethylsiloxane) 1-CHLORO-8-IODO-6-METHYL-4-(4-NITROPHENYL)-2-(2-NITROPHENYLTHIO)-2,3,3A,4,5,9B-HEXAHYDRO-1H-CYCLOPENTA[C]QUINOLINE SALOR-INT L134325-1EA 2,3,5,6-Tetramethyliodobenzene 2,6-DIMETHYL-4-IODOPHENOL PENTAMETHYLIODOBENZENE N,N,N'-TRIMETHYL-N'-(2-HYDROXY-3-METHYL-5-IODO-BENZYL)-1,3-PROPANEDIAMINE DIHYDROCHLORIDE 1-IODO-2,3,4,5-TETRAMETHYLBENZENE OTAVA-BB BB7018670077 SALOR-INT L134317-1EA 1,3-Dimethylbarbituric acid 1,2-Diiodobenzene

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