76464-99-8

Basic information

• Product Name: Benzenemethanamine, N-(2-iodophenyl)-
• Synonyms: N-benzyl-2-iodo-aniline;N-benzyl-o-iodoaniline
• CAS NO: 76464-99-8
• Molecular Formula: C13H12IN
• Molecular Weight: 309.149
• Mol File: 76464-99-8.mol

Chemical Properties

• Boiling Point: 368.7±25.0 °C(Predicted)
• Density: 1.612±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Benzenemethanamine, N-(2-iodophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanamine, N-(2-iodophenyl)-(76464-99-8)
• EPA Substance Registry System: Benzenemethanamine, N-(2-iodophenyl)-(76464-99-8)

Safety Data

• Hazardous Substances Data: 76464-99-8(Hazardous Substances Data)

Upstream product

• 615-43-0 2-iodophenylamine 
• 100-44-7 benzyl chloride 
• 15111-14-5 2-iodo-N-(phenylmethylene)-benzenamine 
• 100-52-7 benzaldehyde 
• 1276611-59-6 tert-butyl benzyl(2-iodophenyl)carbamate 
• 161117-84-6 tert-butyl 2-iodophenylcarbamate 
• 167390-83-2 (E)-N-(2-iodophenyl)-1-phenylmethanimine 
• 100-39-0 benzyl bromide 

Downstream Products

• 87587-25-5 N-benzyl-2-[2-(trimethylsilyl)acetylenyl]aniline 
• 87587-24-4 N-benzyl-2-(hex-1-yn-1-yl)aniline 
• 130013-22-8 2-iodo-N-allyl-N-benzylaniline 
• 1227290-90-5 (E)-1-benzyl-3-(but-1-enyl)-1H-indole 
• 1028196-25-9 N-benzyl-N-(2-iodophenyl)benzamide 
• 1308865-49-7 N,N-dibenzyl-2-iodoaniline 
• 87861-94-7 5-benzyl-5,6-dihydrophenanthridine 
• 73396-87-9 2-iodo-N-allylaniline 
• 1429782-49-9 (Z)-1-benzyl-4-benzylidene-1H-benzo[d][1,3]thiazine-2(4H)-thione 
• 114081-14-0 1-benzyl-3,3-dimethyl-1,3-dihydro-indol-2-one 
• 324738-52-5 benzyl(2-ethynylphenyl)carbamyl chloride 
• 18217-64-6 (E)-1-benzyl-3-(methoxycarbonyl)methylene-1,3-dihydroindol-2-one 

Relevant articles and documents

Metal-Catalyzed Cyclotrimerization Reactions of Cyanamides: Synthesis of 2-Aryl-α-carbolines

The synthesis of annulated 2-aryl-α-carboline heterocycles is described using transition metal catalysis. A linear strategy is described that uses Rh(I) catalysis to form the α-carboline scaffold by [2+2+2] cyclotrimerization. Alternatively, a tandem catalytic approach using a Pd(II) precatalyst afforded the same target molecules by mediating a Sonogashira reaction and a [2+2+2] cyclotrimerization in the same reaction flask. In each case, nine different 2-aryl-α-carbolines have been prepared in high to modest isolated yields.

Modular counter-Fischer?indole synthesis through radical-enolate coupling

A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.

Acid-Promoted Expeditious Syntheses of Aminated Dibenzosultams via Palladium/Norbornene Cooperatively Catalysed C?H Amination/Arylation

Herein we reported a protocol to access aminated benzofused sultams through sequential ortho-amination, followed by ipso-arylation of aryl iodide bearing sulfonamide functional group via palladium/norbornene coorperative catalysis. This reaction has showcased a broad spectrum of substrate scope under mild conditions with moderate to good efficiency. (Figure presented.).

Catalytic and Enantioselective Control of the C–N Stereogenic Axis via the Pictet–Spengler Reaction

An unprecedented example of a chiral phosphoric acid-catalyzed atroposelective Pictet–Spengler reaction of N-arylindoles is reported. Highly enantioenriched N-aryl-tetrahydro-β-carbolines with C?N bond axial chirality are obtained via dynamic kinetic reso

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.

Studies towards the Total Synthesis of Drimentine C. Preparation of the AB and CDEF Ring Fragments

The drimentine family is a class of hybrid isoprenoids derived from actinomycete bacteria. Members of this family display weak antitumor and antibacterial activity. Herein we report our efforts toward the total synthesis of drimentine C using three distinct approaches incorporating palladium-catalyzed cyanoamidation, reductive cross-coupling, and photoredox-catalyzed α-alkylation of an aldehyde as key steps. Our synthetic efforts use a convergent synthesis to assemble the terpenoid and alkaloid portions of drimentine C from readily available l-tryptophan, l-proline, and (+)-sclareolide.

A carboxylate-assisted amination/unactivated C(sp2)-H arylation reactionviaa palladium/norbornene cooperative catalysis

This report describes a carboxylate-assisted palladium-catalysed Catellani reaction, which is compatible withortho-amination and unactivated C(sp2)-H arylation. This method was used to synthesize a series of 1-amino substituted dihydrophenanthridines, phenanthridines and 6H-benzo[c]chromenes. Based on kinetic isotope experiments, the kinetic curve proves that pivalic acid accelerates the reaction rate of unactivated C(sp2)-H activation, and thus this rate can keep up with the five membered aryl-norbornene-palladacycle (ANP) intermediate.

Indazole 2-oxides compound and method for preparing indazole 2-oxides compound for providing a nitrogen heterocyclic compound used as a precursor for drugs

Provided is a method for preparing an indazole 2-oxides compound, which comprises the step of: performing a cyclization reaction on 2-alkynyl aniline compound and tert-butylnitrite represented by formula (1) in the presence of bis(dibenzylideneacetone) palladium so as to produce an indazole 2-oxides compound, in which, in the formulae (1) and (2), R1 , R2 , R3 and R4 are each hydrogen, halogen or alkyl group; X1 represents an alkyl group, a first chemical structure, a second chemical structure or a third chemical structure where T1 , T2 , T3 , T4 and T5 are each hydrogen, halogen, alkoxy group, or alkyl group; X2 represents hydrogen, cycloalkyl group, alkyl group, alkenyl group, thienyl group, unsubstituted phenyl group, or substituted phenyl group, where the substituent is selected from the group consisting of an alkyl group, an alkoxy group, a halogen, a haloalkyl group, -CN, or -NO2.

SPIRALLY CONFIGURED CIS-STILBENE/FLUORENE HYBRID MATERIAL AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME

The invention provides a spirally configured cis-stilbene/fluorene hybrid material and an organic electroluminescent device by using the same. The spirally configured cis-stilbene/fluorene hybrid material has a structure with a general formula (1). In the General formula (1), R' is an alkyl group or represented by General Formula (2), X is represented by CR36R37 or NR38, R36 is represented by General Formula (3), R37 is represented by General Formula (4), R38 is represented by General Formula (5); R1 to R4, R6 to R18 and R39 to R53 are independently selected from the group consisting of hydrogen atom, halogen atom, cyano group, alkyl group, cycloalkyl group, alkoxy group, amino group, haloalkyl group, thioalkyl group, silyl group and alkenyl group, R5 is a hydrogen atom, tert-butyl group or naphthyl group, n is 0 or 1.

Reactivity of Alkyne Insertion and Catalytic Activity of Five- and Six-Membered Cyclometalated Phosphine Complexes of Iridium

Reactions of three aryl-substituted phosphines with [Cp*IrCl2]2 afforded the corresponding five-membered or six-membered cyclometalated iridium complexes (2 or 5,6) via an intramolecular C(sp2)–H bond activation. Insertion reactions of the five-membered cycloiridated complex 2 with PhC≡CPh and PhC≡CCOPh resulted in the corresponding five-membered and six-membered doubly cycloiridated complexes 7 and 8, the formation of which presumably went through the vinylidene rearrangement of alkynes followed by 1,1-insertion; while the reactions of the six-membered cyclometalated complexes 5, 6 with PhC≡CPh or PhC≡CCOPh gave the corresponding eight-membered cycloiridated complexes 9–12 by 1,2-insertion. The hydrosilylation of imines catalyzed by five- or six-membered P-containing cycloiridated complexes were studied, and the results proved that the six-membered cycloiridated complex 5 can be used as an efficient catalyst, which was applied for the hydrosilylation of various imines, especially aldimines. Molecular structures of complexes 9, 10 and 12 were determined by X-ray diffraction.