13194-69-9

Basic information

• Product Name: 2-IODO-5-METHYLANILINE
• Synonyms: 2-IODO-5-METHYLANILINE;3-IODO-5-METHYLANILINE;BenzenaMine,2-iodo-5-Methyl-
• CAS NO: 13194-69-9
• Molecular Formula: C₇H₈IN
• Molecular Weight: 233.05
• Mol File: 13194-69-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 37-39
• Boiling Point: 266.5 °C at 760 mmHg
• Flash Point: 115 °C
• Appearance: /
• Density: 1.791 g/cm³
• Vapor Pressure: 0.0086mmHg at 25°C
• Refractive Index: 1.663
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 2.66±0.10(Predicted)
• CAS DataBase Reference: 2-IODO-5-METHYLANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-IODO-5-METHYLANILINE(13194-69-9)
• EPA Substance Registry System: 2-IODO-5-METHYLANILINE(13194-69-9)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 13194-69-9(Hazardous Substances Data)

Usage

General Description

2-Iodo-5-methylaniline is a chemical compound with the molecular formula C7H8IN. It is a derivative of aniline, with a methyl group and an iodine atom attached to the 2 and 5 positions, respectively. 2-IODO-5-METHYLANILINE is used as a building block in the synthesis of pharmaceuticals, dyes, and other organic compounds. It is also used as an intermediate in the production of agrochemicals and other specialty chemicals. 2-Iodo-5-methylaniline is a solid at room temperature and is typically handled and stored in a controlled environment to prevent exposure and ensure safety.

InChI:InChI=1/C7H8IN/c1-5-2-3-6(8)7(9)4-5/h2-4H,9H2,1H3

Upstream product

• 142-71-2 copper diacetate 
• 64-19-7 acetic acid 
• 108-44-1 1-amino-3-methylbenzene 
• 89-62-3 4-methyl-2-nitroaniline 
• 5326-39-6 4-iodo-3-nitrotoluene 
• 7732-18-5 water 

Downstream Products

• 1608-47-5 4-Methyl-1,2-diiodobenzene 
• 35928-80-4 6-iodo-3-methyl-phenol 
• 117832-10-7 2,4-diiodo-5-methyl-aniline 
• 52164-28-0 N-(2-iodo-5-methylphenyl)acetamide 
• 3652-91-3 2-methyl-9H-carbazole 
• 89641-12-3 2,3,4,6-tetraiodo-toluene 
• 89975-84-8 2,4,6-triiodo-3-methyl-aniline 
• 1014697-61-0 methyl 3-[(2-iodo-5-methylphenyl)amino]propionate 
• 1038778-91-4 (2-iodo-5-methylphenyl)carbamic acid 1,1-dimethylethyl ester 
• 1037493-10-9 5-methyl-2-(phenylethynyl)aniline 
• 1280563-40-7 C₁₂H₁₇NO₃ 
• 1280563-54-3 C₁₄H₁₆F₃NO₄ 
• 1280563-57-6 C₃₅H₃₄F₃NO₆ 
• 1280563-71-4 C₄₄H₅₁F₃N₃O₇P 

Relevant articles and documents

Modular counter-Fischer?indole synthesis through radical-enolate coupling

A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.

Palladium-Catalyzed Incorporation of Two C1 Building Blocks: The Reaction of Atmospheric CO2 and Isocyanides with 2-Iodoanilines Leading to the Synthesis of Quinazoline-2,4(1H,3H)-diones

A Pd-catalyzed insertion and cycloaddition of CO2 and isocyanide into 2-iodoanilines under atmospheric pressure has been developed and affords quinazoline-2,4(1H,3H)-diones through the formation of new C-C, C-O, and C-N bonds under mild conditions. This reaction provides a new and practical method not only for the construction of quinazoline-2,4(1H,3H)-diones but also for the efficient utilization of carbon dioxide.

Synthesis and structural insights of substituted 2-iodoacetanilides and 2-iodoanilines

This study reports a simple and efficient method for the direct iodination of substituted anilines with molecular iodine and copper acetate in acetic acid producing 2-iodoacetanilies and 2-iodoanilines. Employing density functional theory (B3LYP) and MidiX basis set, computational study is performed to calculate equilibrium geometries, IR vibrational frequencies, and thermodynamic properties including change of energy, enthalpy and Gibbs free energies. The optimized geometries indicated longer C-I bond distance (2.133 ?) which makes iodine slightly positive. The partial atomic charge profile and electrostatic potential further confirmed that most of the iodinated products are capable of forming a distinct halogen bonding . The thermodynamic properties disclosed that all iodination reactions are endothermic. Understanding the substituents' effect, molecular frontier orbital (MO) calculations are conducted finding the HOMO, LUMO and HOMO-LUMO gaps for all compounds. The MO calculations revealed that two electron-withdrawing iodine groups have significant influence on lowering the HOMO-LUMO gap compared to one iodine group in the products.