22445-41-6

Basic information

• Product Name: 1-Iodo-3,5-dimethylbenzene
• Synonyms: 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-;4-Iodo-3,5-dimethylbenzoic acidamide
• CAS NO: 22445-41-6
• Molecular Formula: C₈H₉I
• Molecular Weight: 232.06
• EINECS: -0
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Halogen toluene;Iodine Compounds
• Mol File: 22445-41-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: -2.9°C (estimate)
• Boiling Point: 92-94 °C3 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear light yellow/Liquid
• Density: 1.608 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.103mmHg at 25°C
• Refractive Index: n20/D 1.594(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Sparingly soluble (0.014 g/L) (25°C), Calc.
• Sensitive: Light Sensitive
• BRN: 2039353
• CAS DataBase Reference: 1-Iodo-3,5-dimethylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Iodo-3,5-dimethylbenzene(22445-41-6)
• EPA Substance Registry System: 1-Iodo-3,5-dimethylbenzene(22445-41-6)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 22445-41-6(Hazardous Substances Data)

Usage

Description

1-Iodo-3,5-dimethylbenzene, also known as 5-iodo-m-xylene, is an aryl halide that can be synthesized from 5-bromo-m-xylene through a copper-catalyzed halogen exchange reaction using NaI or KI in n-BuOH or DMF solvents. It is a clear light yellow liquid.

Uses

Used in Chemical Synthesis:
1-Iodo-3,5-dimethylbenzene is used as a starting material for the synthesis of various organic compounds, including N-(3,5-xylyl)-N-ethylaniline, an aryl amine. It is also employed in the following studies:
α-Arylation of ketones
Copper-catalyzed N-arylation of imidazoles
Cyanation 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 to form N-Allyl-3,5-dimethylbenzenamine
Copper-catalyzed C-S bond-formation with thiophenol
Synthesis of biphenyl-3,3′,5,5′-tetracarboxylic acid
Radical bromination by N-bromosuccinimide to form 1,3-bis(bromomethyl)-5-iodobenzene
Used in Suzuki Reaction:
1-Iodo-3,5-dimethylbenzene is a versatile reagent in the Suzuki reaction, a cross-coupling process used to form carbon-carbon bonds between aryl and vinyl halides with boronic acids or boronates. This reaction is widely used in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and materials.

InChI:InChI=1/C8H9I/c1-6-3-7(2)5-8(9)4-6/h3-5H,1-2H3

Upstream product

• 108-69-0 3,5-dimethylaminoaniline 
• 108-38-3 m-xylene 
• 4102-53-8 4-iodo-2,6-dimethylaniline 
• 556-96-7 5-bromo-1,3-xylene 
• 87-62-7 2,6-dimethylaniline 
• 4102-48-1 1,4-diiodo-2,6-dimethylbenzene 
• 108-95-2 phenol 
• 172975-69-8 3,5-dimethylphenyl boronic acid 
• 325142-93-6 2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 34907-38-5 tris(3.5-dimethyl phenyl)boroxine 
• 506-78-5 cyanogen iodide 
• 499-06-9 3,5-dimethylbenzoic acid 

Downstream Products

• 121771-61-7 dichloro-3,5-dimethyliodobenzene 
• 30101-07-6 (3,5-dimethylphenyl)diiodoborane 
• 107164-93-2 1,3-bis(bromomethyl)-5-iodobenzene 
• 182616-53-1 PhP(m-xylyl)2 
• 680980-39-6 3,5-dimethyl(diacetoxy-λ³-iodanyl)benzene 
• 120957-65-5 1-(4-methoxyphenoxy)-3,5-dimethylbenzene 
• 223762-69-4 1-(3,5-dimethylphenyl)-1H-imidazole 
• 223762-71-8 1-(3,5-dimethylphenyl)-1H-benzo[d]imidazole 
• 5779-95-3 3,5-dimethylbenzaldehyde 
• 17057-88-4 3,5-dimethylbiphenyl 
• 56-23-5 tetrachloromethane 
• 22445-42-7 3,5-dimethylbenzonitrile 

Relevant articles and documents

Sulfur contamination due to quenching of halogenation reactions with sodium thiosulfate: Resolution of process problems via improved quench protocols

Many metal-mediated cross-couplings involve the use of organic halides, which are usually accessed by halogenation reactions. Cross-couplings are sensitive to the presence of impurities in the halides. This paper describes the origin of one such problematic impurity (sulfur) during the synthesis of organic halides and proposes alternatives to minimize or eliminate its formation.

Visible-Light-Induced Decarboxylative Iodination of Aromatic Carboxylic Acids

A convenient, efficient and practical visible-light-induced decarboxylative iodination of aromatic carboxylic acids has been developed, and the corresponding aryl iodides were obtained in good yields. The method shows some advantages including the use of readily available aromatic carboxylic acids as the starting materials, simple and mild conditions, high efficiency, wide substrate scope and tolerance of various functional groups.

Easy Access to Difluoromethylene-Containing Arene Analogues through Palladium-Catalysed C–H Olefination

An efficient palladium-catalysed ortho-C–H olefination of α,α-difluorophenylacetic acid derivatives using 8-aminoquinoline as a bidentate directing group has been developed. A range of olefinated arenes can thus be synthesized in a concise way. This reaction provides an easy and straightforward route to a panel of difluoromethylated arene analogues in moderate to good yields, with a satisfactory tolerance of common functional groups. Transformation of the products into a variety of other difluoromethylene-containing compounds demonstrates the utility of this method.