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.)

Flash point:

>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 Gravity

1.608

color 

Clear light yellow

Sensitive 

Light Sensitive

BRN 

2039353

InChIKey

ZLMKEENUYIUKKC-UHFFFAOYSA-N

CAS DataBase Reference

22445-41-6(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 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

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

1-Iodo-3,5-dimethylbenzene Usage And Synthesis

Chemical Properties

clear light yellow liquid

Uses

suzuki reaction

Uses

1-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.

Uses

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.

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.

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