1-Iodo-3,5-dimethylbenzene

1-Iodo-3,5-dimethylbenzene
  • CAS No.:22445-41-6

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  1. This product is a chemical product/pharmaceutical intermediate. It is not a drug, an active pharmaceutical ingredient (API), or a pharmaceutical-grade material. It has not been granted a drug approval number or a Chemical Drug Substance Approval Notice, has not passed drug-related review and approval, and is not manufactured, tested, or released in accordance with pharmaceutical GMP.
  2. This product is intended solely for non-clinical research, process development, quality studies, further chemical processing, or chemical synthesis. It must not be used in drug-product manufacturing, clinical trials, clinical diagnosis, or administration to humans or animals, or be sold, used as an input, submitted for regulatory filing, or released as an API or pharmaceutical material.
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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 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.

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