1308865-49-7

Basic information

• Product Name: N,N-dibenzyl-2-iodoaniline
• Synonyms: N,N-dibenzyl-2-iodoaniline
• CAS NO: 1308865-49-7
• Molecular Weight: 399.274
• Mol File: 1308865-49-7.mol

Chemical Properties

• CAS DataBase Reference: N,N-dibenzyl-2-iodoaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-dibenzyl-2-iodoaniline(1308865-49-7)
• EPA Substance Registry System: N,N-dibenzyl-2-iodoaniline(1308865-49-7)

Safety Data

• Hazardous Substances Data: 1308865-49-7(Hazardous Substances Data)

Upstream product

• 615-43-0 2-iodophenylamine 
• 100-39-0 benzyl bromide 
• 76464-99-8 N-benzyl-2-iodoaniline 
• 100-52-7 benzaldehyde 
• 15111-14-5 2-iodo-N-(phenylmethylene)-benzenamine 
• 1028196-25-9 N-benzyl-N-(2-iodophenyl)benzamide 

Downstream Products

• 87861-94-7 5-benzyl-5,6-dihydrophenanthridine 
• 1516899-07-2 N,N-dibenzyl-2-(phenylethynyl)aniline 
• 52604-17-8 1,3-dibenzyl-2-phenyl-1H-indole 
• 1417628-01-3 (E)-4-(2-(dibenzylamino)phenyl)but-3-en-2-one 
• 142677-04-1 1-benzyl-2-phenyl-1H-indole-3-carbaldehyde 
• 1417628-09-1 (Z)-4-(2-(dibenzylamino)phenyl)but-3-en-2-one 
• 1417628-48-8 C₂₂H₁₇N⁽¹⁸⁾O 
• 1443006-57-2 C₂₅H₂₇NSi 
• 1438277-71-4 1-benzyl-2-phenyl-2,3-dihydroquinolin-4(1H)-one 
• 1070413-73-8 N,N-dibenzyl-2-ethynylaniline 

Relevant articles and documents

Unexpected Rearrangement of 2-Bromoaniline under Biphasic Alkylation Conditions

Alkylation of 2-bromoaniline with benzyl bromide under ostensibly basic N-alkylation conditions resulted in migration of bromine from the 2- to the 4-aryl position. Herein we report our studies to elucidate the mechanism of this rearrangement with the objective of suppressing this unexpected outcome. We find that careful choice of reagents is critical, and that this behavior may be extrapolated to alkylation reactions of electron-rich bromo- and iodoanilines in general.

Ligand-Free Heck Reactions of Aryl Iodides: Significant Acceleration of the Rate through Visible Light Irradiation at Ambient Temperature

A mild Heck reaction of aryl iodides and olefins was realized by the cooperation of a palladium and a photoredox catalyst under the irradiation of visible light. This protocol works well to synthesize stilbenes with high Z/E ratios and (E)-cinnamates in the absence of ligands at ambient temperature. Control experiments revealed that palladium salt, visible light and photoredox catalyst were all crucial for the achievement of this cross-coupling under mild conditions. (Figure presented.).

A new synthesis of indoles via intramolecular cyclization of ?-alkynyl N,N-dialkylanilines promoted by KOt-Bu/DMSO

2-Aryl indoles could be prepared in excellent yields via the intramolecular cyclization of ?-alkynyl N,N-dialkylanilines. The reaction is efficiently promoted by the catalytic amount of KOt-Bu in DMSO at room temperature. A reaction mechanism involving α-

A new synthesis of indoles via intramolecular cyclization of ο-alkynyl N,N-dialkylanilines promoted by KOt-Bu/DMSO

2-Aryl indoles could be prepared in excellent yields via the intramolecular cyclization of ο-alkynyl N,N-dialkylanilines. The reaction is efficiently promoted by the catalytic amount of KOt-Bu in DMSO at room temperature. A reaction mechanism involving α-

An efficient approach to 1,2,3-trisubstituted indole via rhodium catalyzed carbene Csp3-H bond insertion

A method for convenient synthesis of N-alkyl-2-aryl-indole-3-carbaldehyde has been described. A variety of highly valuable indolyl aldehydes have been prepared through this method. Electron donating groups on both aromatic rings (anilinyl and benzyl) facilitate the formation of the desired products. A benzylic C-H insertion by rhodium carbene is the key step for this transformation. This journal is

Oxygen switch in visible-light photoredox catalysis: Radical additions and cyclizations and unexpected C-C-bond cleavage reactions

Visible light photoredox catalyzed inter- and intramolecular C-H functionalization reactions of tertiary amines have been developed. Oxygen was found to act as chemical switch to trigger two different reaction pathways and to obtain two different types of products from the same starting material. In the absence of oxygen, the intermolecular addition of N,N-dimethyl-anilines to electron-deficient alkenes provided γ-amino nitriles in good to high yields. In the presence of oxygen, a radical addition/cyclization reaction occurred which resulted in the formation of tetrahydroquinoline derivatives in good yields under mild reaction conditions. The intramolecular version of the radical addition led to the unexpected formation of indole-3-carboxaldehyde derivatives. Mechanistic investigations of this reaction cascade uncovered a new photoredox catalyzed C-C bond cleavage reaction.

O-(Trialkylstannyl)anilines and their utility in Migita-Kosugi-Stille cross-coupling: Direct introduction of the 2-aminophenyl substituent

We have developed shelf- and air-stable ortho-stannylated aniline reagents that can directly be coupled with alkenyl and aryl halides via Migita-Kosugi-Stille cross-coupling. We report (i) the efficient preparation of o-(tributylstannyl)aniline (2a) and o-(trimethylstannyl)aniline (2b), (ii) the comparison of the reactivities of 2a and 2b with those of related organostannanes in cross-coupling reaction with an alkenyl halide, and (iii) the cross-coupling of 2a and 2b with a series of arylhalides and triflate.

Metal-free oxidation/C(sp3)iH functionalization of unactivated alkynes using pyridine-N-oxide as the external oxidant

Externally yours: 2,3-Dihydroquinolin-4(1H)-ones are obtained in moderate to good yields (40-84 %, see scheme) in a metal-free oxidation/C(sp 3)iH functionalization of unactivated aryl alkynes. 2,6-Dichloropyridine-N-oxide is used as an external oxidant. In the reaction, a Bronsted acid, not a metal, plays a key role in the triple CiC bond activation. Copyright

Potassium tert-butoxide promoted intramolecular arylation via a radical pathway

Potassium tert-butoxide mediated intramolecular cyclization of aryl ethers, amines, and amides was efficiently performed under microwave irradiation to provide the corresponding products in high regioisomeric ratios. The reaction proceeds via single-electron transfer to initiate the formation of an aryl radical, followed by a kinetically favored 5-exo-trig and subsequent ring expansion.