1616707-08-4

Basic information

• Product Name: N-benzyl-4-bromo-2-iodoaniline
• Synonyms: N-benzyl-4-bromo-2-iodoaniline
• CAS NO: 1616707-08-4
• Molecular Weight: 388.046
• Mol File: 1616707-08-4.mol

Chemical Properties

• CAS DataBase Reference: N-benzyl-4-bromo-2-iodoaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyl-4-bromo-2-iodoaniline(1616707-08-4)
• EPA Substance Registry System: N-benzyl-4-bromo-2-iodoaniline(1616707-08-4)

Safety Data

• Hazardous Substances Data: 1616707-08-4(Hazardous Substances Data)

Upstream product

• 66416-72-6 4-bromo-2-iodoaniline 
• 100-39-0 benzyl bromide 
• 100-52-7 benzaldehyde 

Downstream Products

• 79183-44-1 1-benzyl-5-bromoisatin 
• 1741-50-0 6-bromo-2-phenyl-1H-benzo[d]imidazole 
• 1615653-18-3 1-benzyl-6-bromo-3-diethoxyphosphoryloxy-4-methylene-3-phenyl-3,4-dihydro-2-quinolone 
• 1615653-06-9 N-benzyl-N-(4-bromo-2-ethynylphenyl)-2-oxo-2-phenylacetamide 

Relevant articles and documents

Site-Selective Double and Tetracyclization Routes to Fused Polyheterocyclic Structures by Pd-Catalyzed Carbonylation Reactions

In this contribution, we report novel palladium-catalyzed carbonylative cascade approaches to highly functionalized polyheterocyclic structures. The Pd-catalyzed carbonylative process involves the regioselective insertion of one to three CO molecules and the sequential ordered formation of up to eight new bonds (one C-O, two C-C, five C-N). The exclusive formation of six-membered heterocycles is elucidated by detailed modeling studies.

Copper-Catalyzed Double C-N Bond Formation for the Synthesis of Diverse Benzimidazoles from N -Alkyl-2-iodoaniline and Sodium Azide

An efficient approach to the synthesis of benzimidazole derivatives has been achieved by copper-catalyzed double C-N bonds formation of N-alkyl-2-iodoaniline and sodium azide. The reaction was supposed to proceed through copper-catalyzed tandem reaction of SNAr reaction, aerobic oxidation of C(sp3)-H bond and intramolecular C-N bond formation sequence. Structurally diverse 2-aryl, alkenyl and alkyl benzoimidazole derivatives were assembled by this methodology.

One-pot strategy of copper-catalyzed synthesis of 1,2-disubstituted benzimidazoles

A simple, one-pot and copper-catalyzed coupling reaction for the construction of 1,2-disubstituted benzimidazole derivatives is described. A low-cost copper salt and a weak base K3PO4 were utilized in this reaction. A variety of 1,2-disubstituted benzimidazoles were obtained in moderate to excellent yields.

Bis(dibenzylideneacetone)palladium(0)/tert-Butyl Nitrite- Catalyzed Cyclization of o-Alkynylanilines with tert-Butyl Nitrite: Synthesis and Applications of Indazole 2-Oxides

An efficient method for the synthesis of 1-benzyl/arylindazole 2-oxides via a bis(dibenzylideneacetone)palladium(0) [Pd(dba)2]/tert-butyl nitrite (TBN)-catalyzed reaction of o-alkynylaniline derivatives with TBN is reported. The overall transfo

Direct Reductive Amination of Aldehydes via Environmentally Benign Bentonite-Gold Nanohybrid Catalysis

An efficient, green and reliable method for the direct reductive amination of aldehydes was developed using an environmentally benign bentonite-gold nanohybrid catalyst. Use of this heterogeneous catalyst affords a variety of secondary amines in excellent yield under ambient reaction conditions in the presence of phenyldimethylsilane as mild hydride donor. The catalyst is recyclable, selective and is well applicable for the gram-scale preparation of secondary amines. (Figure presented.).

A Palladium-Catalyzed Double Carbonylation Approach to Isatins from 2-Iodoanilines

A high-yielding procedure for the synthesis of isatins has been developed. Sequential Pd-catalyzed double carbonylation of 2-iodoanilines with near stoichiometric amounts of CO followed by acid-promoted cyclization readily affords an array of isatins. The conversion of 2-iodoanilines to isatins in good to excellent yields was found to proceed with good functional group tolerance. This protocol proved adaptable to 13C-isotope labeling of isatins, which was extended to the synthesis of the 13C-isotope labeled antiviral drug metisazone and the experimental anti-schizophrenia drug ML137.

Pd(ii)-catalyzed ligand controlled synthesis of methyl 1-benzyl-1H-indole- 3-carboxylates and bis(1-benzyl-1H-indol-3-yl)methanones

A simple change of ligand and solvent allows controlled, effective switching between cyclization-carbonylation and cyclization-carbonylation- cyclization-coupling (CCC-coupling) reactions of 2-alkynylanilines catalyzed by palladium(ii). The use of a [Pd(tfa)2(box)] catalyst in iPrOH afforded symmetrical ketones bearing two indoles in good yields; replacing the catalyst and solvent with Pd(tfa)2 and DMSO-MeOH led to the formation of methyl 1-benzyl-1H-indole-3-carboxylates in good yields. This journal is

Intramolecular cyclization of alkynyl α-ketoanilide utilizing [1,2]-phospha-brook rearrangement catalyzed by phosphazene base

A novel catalytic cyclization reaction of alkynyl α-ketoanilide was developed by utilizing the [1,2]-phospha-Brook rearrangement. This reaction involves the generation of an amide enolate via the umpolung process, that is the addition of dialkyl phosphite to a keto moiety followed by the [1,2]-phospha-Brook rearrangement, and the subsequent intramolecular addition of the enolate to an alkyne to afford 3,4-dihydro-2-quinolone derivatives. Under high-temperature reaction conditions, further rearrangement of the allylic phosphate moiety occurs to provide 2-quinolone derivatives.