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

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

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 
• 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 
• 1372868-27-3 4-(methylamino)-N-(phenylcarbamoyl)benzamide 
• 1440912-64-0 [¹³C]-(E)-4-(4-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)styryl)-N-methylaniline 
• 556-21-8 4-(methylamino)benzaldehyde 

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.

Efficient methylation of anilines with methanol catalysed by cyclometalated ruthenium complexes

Cyclometalated ruthenium complexes4-10allow the effective methylation of anilines with methanol to selectively giveN-methylanilines. This hydrogen autotransfer procedure proceeds under mild conditions (60 °C) in a practical manner (NaOH as base). Mechanistic investigations suggest an active homogenous ruthenium complex and β-hydride elimination of methanol as the rate determining step.

Novel quinoline-based fluorescent bioimaging probe, KSNP117, for sentinel lymph node mapping

Fluorescent imaging agents with biocompatibility and high sensitivity are urgently required for the accurate detection of sentinel lymph nodes (SLNs). Herein, we report the design of a novel quinoline-based fluorescent probe, designated KSNP117, which can be applied as a biomedical imaging agent in the sensitive and quantitative detection of SLNs. KSNP117 exerted no adverse effects on the proliferation of ovary and immune cells and also showed excellent serum stability with photo-brightening effects.In vivofluorescent imaging revealed the accumulation of KSNP117 in the SLNs of nude mice within 10 min post injection, withoutin vivotoxicity, which was consistent with the findings ofex vivoimaging. These results support the potential of KSNP117 as a promising lymphatic tracer for biomedical imaging applications.

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.

Selective N -monomethylation of primary anilines with the controllable installation of N -CH2D, N -CHD2, and N -CD3units

The selective N-monomethylation of primary anilines was realized by the use of the Me3N-BH3/N,N-dimethylformamide (DMF) system as the methyl source. This method also allows for the controllable introduction of N-CH2D, N-CHD2, and N-CD3 units with high lev

Bimetallic Bis-NHC-Ir(III) Complex Bearing 2-Arylbenzo[d]oxazolyl Ligand: Synthesis, Catalysis, and Bimetallic Effects

Herein, an unprecedented bimetallic bis-NHC Cp*Ir complex 1 bearing 2-arylbenzo[d]oxazolyl and NHC ligands is reported. A significant increase in activity was observed for N-methylation of amines and reduction of aldehydes with MeOH catalyzed by 1 compared to the monometallic analogues (2-11). Under the optimal conditions, it showed to be highly effective in N-methylation of nitroarenes with MeOH as both C1 and H2 source. Substrates, including aromatic amines, ketones, and nitro compounds with various functional groups, can be well-tolerated. Mechanistic studies and DFT calculation highlight the significance of bimetallic centers cooperativity.

Rh(III)-catalyzed N-nitroso-directed C-H olefination polymerization

Transition metal-catalyzed directed C-H functionalization promises a straightforward route to polymerization but remains highly underexplored. We report herein the development of a polymer synthesis protocol based on Rh(III)-catalyzed N-nitroso-directed C-H olefination reaction. The single bifunctional monomer approach allows the high-yield generation of polymers with relatively narrow PDI under mild conditions. Further convenient denitrosation transformation furnishes responsive fluorescent polymers with metal ion-selective quenching behaviors. The high Hg2+ selectivity observed in one system provides a handy enabling tool for detecting this hazardous species.

Sodium Triethylborohydride-Catalyzed Controlled Reduction of Unactivated Amides to Secondary or Tertiary Amines

The first transition-metal-free catalytic protocol for controlled reduction of amide functions using cheap and bench-stable hydrosilanes as reducing agents has been established. By altering the hydrosilane and solvent, the new method enables the selective cleavage of unactivated C-O bonds in amides and allows the C-N bonds to selectively break via the deacylated cleavage. Overall, this novel process may offer a versatile alternative to current methodologies employing stoichiometric metal systems for the controlled reduction of carboxamides.

Sodium Triethylborohydride-Catalyzed Controlled Reduction of Unactivated Amides to Secondary or Tertiary Amines

The first transition-metal-free catalytic protocol for controlled reduction of amide functions using cheap and bench-stable hydrosilanes as reducing agents has been established. By altering the hydrosilane and solvent, the new method enables the selective cleavage of unactivated C-O bonds in amides and allows the C-N bonds to selectively break via the deacylated cleavage. Overall, this novel process may offer a versatile alternative to current methodologies employing stoichiometric metal systems for the controlled reduction of carboxamides.