1-Iodo-3,5-dimethylbenzene

Base Information

• Chemical Name: 1-Iodo-3,5-dimethylbenzene
• CAS No.: 22445-41-6
• Molecular Formula: C8H9I
• Molecular Weight: 232.064
• Hs Code.: 29039990
• European Community (EC) Number: 629-121-2
• DSSTox Substance ID: DTXSID90176985
• Nikkaji Number: J903.458G
• Wikidata: Q72483556
• Mol file: 22445-41-6.mol

Synonyms:1-iodo-3,5-dimethylbenzene

Chemical Property of 1-Iodo-3,5-dimethylbenzene

Chemical Property:

• Appearance/Colour: Clear light yellow liquid
• Vapor Pressure: 0.103mmHg at 25°C
• Melting Point: -2.9°C (estimate)
• Refractive Index: n20/D 1.594(lit.)
• Boiling Point: 229.9 °C at 760 mmHg
• Flash Point: 99.3 °C
• PSA: 0.00000
• Density: 1.61 g/cm³
• LogP: 2.90800
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Light Sensitive
• Solubility.: Sparingly soluble (0.014 g/L) (25°C), Calc.
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 231.97490
• Heavy Atom Count: 9
• Complexity: 80.6

Purity/Quality:

99% ^*data from raw suppliers

1-Iodo-3,5-dimethylbenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, C
• Hazard Codes: Xi,C
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1)I)C
• Uses: suzuki reaction 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. 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.

Technology Process of 1-Iodo-3,5-dimethylbenzene

There total 17 articles about 1-Iodo-3,5-dimethylbenzene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 77.0%

3,5-dimethylphenyl boronic acid (172975-69-8) → 3,5-dimethylphenyl iodide (22445-41-6)

Guidance literature:

With 1,10-Phenanthroline; oxygen; potassium iodide; copper(ll) bromide; In N,N-dimethyl-formamide; at 80 ℃; for 20h;

DOI:10.1016/j.tetlet.2011.02.075

Reference yield: 77.0%

3,5-dimethylaminoaniline (108-69-0) → 3,5-dimethylphenyl iodide (22445-41-6)

Guidance literature:

3,5-dimethylaminoaniline; With sulfuric acid; sodium nitrite; In water; acetone; at 0 ℃; for 1.75h;

With potassium iodide; In water; acetone; at 20 ℃;

DOI:10.1021/op700227p

Reference yield: 75.0%

4-iodo-2,6-dimethylaniline (4102-53-8) → 3,5-dimethylphenyl iodide (22445-41-6) + 1,4-diiodo-2,6-dimethylbenzene (4102-48-1)

Guidance literature:

4-iodo-2,6-dimethylaniline;

DOI:10.1002/1099-0690(200007)2000:14<2663::AID-EJOC2663>3.0.CO;2-Y

upstream raw materials:

3,5-dimethylaminoaniline

m-xylene

4-iodo-2,6-dimethylaniline

5-bromo-1,3-xylene

Downstream raw materials:

(3,5-dimethylphenyl)diiodoborane

PhP(m-xylyl)2

1-(4-methoxyphenoxy)-3,5-dimethylbenzene

1-(3,5-dimethylphenyl)-1H-benzo[d]imidazole

Refernces

• 1、 Jones, Dafydd D. L.,Douair, Iskander,Maron, Laurent,Jones, Cameron. "Photochemically Activated Dimagnesium(I) Compounds: Reagents for the Reduction and Selective C?H Bond Activation of Inert Arenes". . p. 7087 - 7092. Retrieved 2021/03/01.
• 2、 Jin, Xiaodong,Davies, Robert P.. "Copper-catalysed aromatic-Finkelstein reactions with amine-based ligand systems". . p. 2110 - 2117. Retrieved 2017/07/22.