698-02-2

Basic information

• Product Name: 2-iodo-N,N-dimethylaniline
• Synonyms: Aniline, o-iodo-N,N-dimethyl-; o-Iodo-N,N-dimethylaniline
• CAS NO: 698-02-2
• Molecular Formula: C₈H₁₀IN
• Molecular Weight: 247.0762
• Mol File: 698-02-2.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 245.5°C at 760 mmHg
• Flash Point: 102.3°C
• Density: 1.652g/cm³
• Vapor Pressure: 0.0286mmHg at 25°C
• Refractive Index: 1.634
• CAS DataBase Reference: 2-iodo-N,N-dimethylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-iodo-N,N-dimethylaniline(698-02-2)
• EPA Substance Registry System: 2-iodo-N,N-dimethylaniline(698-02-2)

Safety Data

• Hazardous Substances Data: 698-02-2(Hazardous Substances Data)

Upstream product

• 698-00-0 2-bromo-N,N-dimethylaniline 
• 124-38-9 carbon dioxide 
• 615-43-0 2-iodophenylamine 
• 50-00-0 formaldehyd 
• 57056-93-6 N-methyl-2-iodoaniline 
• 121-69-7 N,N-dimethyl-aniline 
• 88-74-4 2-nitro-aniline 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 219605-51-3 N,N-dimethyl-2-((trimethylsilyl)ethynyl)benzenamine 
• 1001652-49-8 (CH₃)2NC₆H₄P(CH₃)(C₆H₅)(BH₃) 
• 603-33-8 triphenylbismuthane 
• 677027-07-5 trans-[Pd(C₆H₄NMe₂-2)I(PPh₃)2] 
• 1346165-10-3 N,N-dimethyl-2-(2-methylphenylethynyl)aniline 
• 1620742-32-6 C₁₆H₁₄BrN 
• 1433460-53-7 N,N-dimethyl-2-(1H-pyrrol-1-yl)aniline 

Relevant articles and documents

Intramolecular Addition of a Dimethylamino C(sp 3)-H Bond across C-C Triple Bonds Using IrCl(DTBM-SEGPHOS)(ethylene) Catalyst: Synthesis of Indoles from 2-Alkynyl- N -methylanilines

Intramolecular addition of a C(sp 3)-H bond of the dimethylamino group across the C-C triple bond in 2-alkynyl- N, N -dimethylanilines is effectively catalyzed by a new iridium complex, IrCl(DTBM-SEGPHOS)(C 2H 4), in mesitylene at 150 °C. The intramolecular C(sp 3)-H addition is followed by double-bond isomerization to afford 3-substituted indoles in good to high yields.

Au-promoted Pd-catalyzed arylative cyclization of N,N-dimethyl-o-alkynylaniline with aryl iodides: Access to 2,3-diaryl indoles and mechanistic insight

We have developed a Au-promoted Pd-catalyzed cyclization/cross-coupling of N,N-dimethyl-o-alkynylaniline with aryl iododes to synthesize 2,3-diarylindoles under mild and base-free conditions. A related vinyl-Au species has been isolated through Au-promoted cyclization of N,N-dimethyl-o-alkynylaniline and structurally characterized. Further study on its reactivity suggests the vinyl-Au species might be out of catalytic cycle, and PhPd(OTf)(PPh3)2 is probably the reaction intermediate.

Mesoionic N-heterocyclic olefin catalysed reductive functionalization of CO2for consecutiveN-methylation of amines

A mesoionic N-heterocyclic olefin (mNHO) was introduced as a metal-free catalyst for the reductive functionalization of CO2leading to consecutive doubleN-methylation of primary amines in the presence of 9-borabicyclo[3.3.1]nonane (9-BBN). A wide range of secondary amines and primary amines were successfully methylated under mild conditions. The catalyst sustained over six successive cycles ofN-methylation of secondary amines without compromising its activity, which encouraged us to check its efficacy towards doubleN-methylation of primary amines. Moreover, this method was utilized for the synthesis of two commercially available drug molecules. A detailed mechanistic cycle was proposed by performing a series of control reactions along with the successful characterisation of active catalytic intermediates either by single-crystal X-ray study or by NMR spectroscopic studies in association with DFT calculations.