60577-34-6

Basic information

• Product Name: 4-IODO-N-METHYLANILINE
• Synonyms: 4-IODO-N-METHYLANILINE;(4-IODO-PHENYL)-METHYL-AMINE;4-Methylaminophenyl iodide;N-Methyl-4-iodoaniline;p-Iodo-N-methylaniline
• CAS NO: 60577-34-6
• Molecular Formula: C₇H₈IN
• Molecular Weight: 233.04959
• Mol File: 60577-34-6.mol
• Article Data: 49

Chemical Properties

• Melting Point: 28-29 °C(Solv: hexane (110-54-3))
• Boiling Point: 261.1 °C at 760 mmHg
• Flash Point: 111.7 °C
• Appearance: /
• Density: 1.779 g/cm³
• Vapor Pressure: 0.0118mmHg at 25°C
• Refractive Index: 1.667
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: 3.82±0.12(Predicted)
• CAS DataBase Reference: 4-IODO-N-METHYLANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-IODO-N-METHYLANILINE(60577-34-6)
• EPA Substance Registry System: 4-IODO-N-METHYLANILINE(60577-34-6)

Safety Data

• Hazardous Substances Data: 60577-34-6(Hazardous Substances Data)

Usage

Description

4-IODO-N-METHYLANILINE, also known as 4-iodo-N-methylbenzenamine, is an organic compound that belongs to the class of aromatic amines. It is characterized by the presence of an iodine atom at the 4th position and a methyl group attached to the nitrogen atom. 4-IODO-N-METHYLANILINE is known for its reactivity and is widely used in various chemical processes and applications.

Uses

Used in Chemical Synthesis:
4-IODO-N-METHYLANILINE is used as an intermediate in the synthesis of various organic compounds, particularly in the pharmaceutical and agrochemical industries. Its unique structure allows for further functionalization and modification, making it a versatile building block for the development of new molecules with potential applications in these fields.
Used in Direct N-Methylation:
4-IODO-N-METHYLANILINE is used as a reactant in a general efficient method for direct N-methylation of aromatic primary amines with methanol. This process is significant because it simplifies the synthesis of N-methylated aromatic amines, which are important intermediates in the production of various chemicals, pharmaceuticals, and agrochemicals.
Used in Dye Manufacturing:
4-IODO-N-METHYLANILINE is used as a starting material in the production of certain dyes and pigments. Its reactivity and the presence of the iodine atom make it suitable for the synthesis of dyes with specific color properties and stability.
Used in Analytical Chemistry:
4-IODO-N-METHYLANILINE can be employed as a reagent in analytical chemistry for the detection and quantification of various compounds. Its unique structure and reactivity make it a valuable tool for the development of new analytical methods and techniques.

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

Upstream product

• 6393-17-5 N-(4-iodo-phenyl)-formamide 
• 100-61-8 N-methylaniline 
• 641612-91-1 2,2,2-trifluoro-N-(4-iodophenyl)-N-methylacetamide 
• 540-37-4 p-aminoiodobenzene 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 698-70-4 4-Iodo-N,N-dimethylaniline 
• 579-10-2 N-acetyl-N-methylaniline 
• 62404-59-5 4-(N-acetyl-N-methylamino)iodobenzene 
• 616-38-6 carbonic acid dimethyl ester 
• 50-00-0 formaldehyd 
• 68-12-2 N,N-dimethyl-formamide 
• 636-98-6 p-nitrobenzene iodide 
• 591-50-4 iodobenzene 

Downstream Products

• 143937-66-0 N-(4-iodophenyl)-N-methylbenzenesulfonamide 
• 55239-50-4 C₈H₇ClINO 
• 680185-35-7 6-[(4-iodo-phenyl)-methyl-amino]-hexan-1-ol 
• 916587-44-5 methyl-(4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pnenyl)-carbamic acid tert-butyl ester 
• 119754-15-3 4-ethynyl-N-methylbenzenamine 
• 641612-92-2 2-chloro-N-(4-iodophenyl)-N-methylacetamide 
• 618439-07-9 4-iodo-N-methyl-N-(3-chloro-2-hydroxypropyl)aniline 
• 1128054-21-6 C₁₁H₁₂IN 
• 1233957-30-6 N-methyl-4-[(trimethylsilyl)ethynyl]aniline 
• 1295606-05-1 N-methyl-4-(phenylethynyl)aniline 
• 1374418-19-5 C₂₃H₁₆BrN 
• 1374418-25-3 C₃₄H₂₇N₃O₅ 

Relevant articles and documents

Borane-Trimethylamine Complex as a Reducing Agent for Selective Methylation and Formylation of Amines with CO2

We report herein that a borane-trimethylamine complex worked as an efficient reducing agent for the selective methylation and formylation of amines with 1 atm CO2 under metal-free conditions. 6-Amino-2-picoline serves as a highly efficient catalyst for the methylation of various secondary amines, whereas in its absence, the formylation of primary and secondary amines was achieved in high yield with high chemoselectivity. Mechanistic studies suggest that the 6-amino-2-picoline-borane catalytic system operates like an intramolecular frustrated Lewis pair to activate CO2.

Synthesis of N-Alkyl Anilines from Arenes via Iron-Promoted Aromatic C-H Amination

We report both an intermolecular C-H amination of arenes to access N-methylanilines and an intramolecular variant for the synthesis of tetrahydroquinolines. A newly developed, highly electrophilic aminating reagent was key for the direct synthesis of unprotected N-methylanilines from simple arenes. The reactions display a broad functional group tolerance and employ catalytic amounts of a benign iron salt under mild reaction conditions.

A novel DMSO-assisted regioselective iodination of aniline analogues

A metal- and oxidant-free electrophilic iodination of aniline analogues was achieved in high to excellent yields at room temperature in MTBE with 0 or 3.5 equivalents of DMSO. Examined substituents include N-alkyl, N,N-dialkyl, N-morpholinyl and N-piperazinyl as well as methyl, Br, CN and CO2CH3 aryl ring substitutions.