392510

1-Iodo-3,5-dimethylbenzene

99%

• Synonym(s): 5-Iodo-m-xylene
• Linear Formula: (CH₃)₂C₆H₃I
• CAS Number: 22445-41-6
• Molecular Weight: 232.06
• MDL number: MFCD00060659
• UNSPSC Code: 12352100
• PubChem Substance ID: 24864461
• NACRES: NA.22

Properties

• Assay: 99%
• form: liquid
• refractive index: n20/D 1.594 (lit.)
• bp: 92-94 °C/3 mmHg (lit.)
• density: 1.608 g/mL at 25 °C (lit.)
• SMILES string: Cc1cc(C)cc(I)c1
• InChI: 1S/C8H9I/c1-6-3-7(2)5-8(9)4-6/h3-5H,1-2H3
• InChI key: ZLMKEENUYIUKKC-UHFFFAOYSA-N

Description

General description

1-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.

Application

1-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.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): 235.4 °F - closed cup
• Flash Point(C): 113 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves