53279-83-7

Usage

Uses

Used in Organic Synthesis:
(2-AMINO-5-IODOPHENYL)METHANOL is used as a reagent in organic synthesis for its ability to facilitate the creation of various complex organic compounds. Its unique structure allows it to participate in a range of chemical reactions, making it a valuable component in the synthesis process.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (2-AMINO-5-IODOPHENYL)METHANOL is utilized as a starting material for the production of different pharmaceuticals and fine chemicals. Its properties contribute to the development of new and effective medications, enhancing the range of treatments available.
Used in Medicinal Chemistry:
(2-AMINO-5-IODOPHENYL)METHANOL also has potential applications in the field of medicinal chemistry, where it serves as a foundation for the research and development of new drugs. Its unique chemical structure offers opportunities for innovation in drug design and the advancement of medical treatments.

Upstream product

• 35674-28-3 5-iodo-2-nitrobenzoic acid 
• 5344-90-1 2-Aminobenzyl alcohol 
• 936114-10-2 methyl 5-nitro-2-[(5S)-5-{[(tert-butyl)dimethylsilyloxyethyl]}-2-oxo-1-pyrrolidinyl]benzoate 
• 5326-47-6 2-amino-5-iodobenzoic acid 
• 936114-41-9 methyl 5-amino-2-[(5S)-5-{[(tert-butyl)dimethylsilyiloxyethyl]}-2-oxo-1-pyrrolidinyl]benzoate 
• 936114-46-4 methyl 5-iodo-2-[(5S)-5-(hydroxyethyl)-2-oxo-1-pyrrolidinyl]benzoate 
• 936114-30-6 methyl 5-iodo-2-[(5S)-5-(ethenyl)-2-oxo-1-pyrrolidinyl]benzoate 
• 77317-55-6 methyl 2-amino-5-iodobenzoate 

Downstream Products

• 99471-71-3 2-amino-5-iodobenzaldehyde 
• 247571-87-5 C₁₄H₂₀INO₂Si 
• 76417-04-4 (+/-)-virantmycin 
• 887260-98-2 2-[(2-hydroxymethyl-4-iodo-phenylamino)-methylene]malonic acid diethyl ester 
• 75388-59-9 1,2-dihydro-2-trichloromethyl-4H-benzo[d]-[1,3]-oxazine-6-carbonitrile 
• 1004530-93-1 (2-(2-nitrobenzylamino)-5-iodophenyl)methanol 
• 1245786-12-2 (2-azido-5-iodophenyl)methanol 
• 1128-62-7 6-iodo-2-methylquinoline 
• 3881-41-2 6-iodo-2-phenylquinoline 

Relevant academic research and scientific papers

Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C-O Coupling

A convenient approach to assemble 1,2,3-triazole-fused 4 H -3,1-benzoxazines has been developed. Diverse alcohol-tethered 5-iodotriazoles, readily accessible by a modified protocol of Cu-catalyzed (3+2)-cycloaddition, were utilized as precursors of the target fused heterocycles. The intramolecular C-O coupling proceeded efficiently under base-mediated transition-metal-free conditions, furnishing cyclization products in yields up to 96%. Suppression of the competing reductive cleavage of the C-I bond was achieved by the use of Na 2CO 3in acetonitrile at 100 °C. This practical and cost-effective procedure features a broad substrate scope and valuable functional group tolerance.

Metal-Free C-C/C-N/C-C Bond Formation Cascade for the Synthesis of (Trifluoromethyl)sulfonylated Cyclopenta[ b]indolines

A bis(triflyl)ethylation [triflyl = (trifluoromethyl)sulfonyl] inserted into a sequential cyclization cascade resulted in the direct formation of gem-bis(triflyl)ated cyclopenta[b]indolines from anilide-derived allenols and alkenols. This catalyst- and irradiation-free sequence facilitated the efficient preparation of functionalized tricyclic indoline cores bearing two contiguous stereocenters. The formed cyclopenta[b]indolines can be easily transformed into a wide variety of triflylated indolines, including the tetracycle ring system found in polyveoline.

A Convenient Formal [4+2] Heterocylization Route to Bis(triflyl)tetrahydroquinolines

We report the sustainable and efficient synthesis of a new type of quinoline derivatives bearing one or two SO2CF3 groups. The protocol is metal-, catalyst- and irradiation-free, involves the use of readily available and stable precursors, and avoids the formation of side products. Also, the mild conditions of the process allow the tolerance of a wide range of functional groups.

Preparation and Application of α-Imino Ketones through One-Pot Tandem Reactions Based on Heyns Rearrangement

α-Imino ketone is a useful building block for the preparation of α-amino ketones and α-amino alcohols. However, its preparation has been seldomly seen. Herein, a metal-free and operationally simple strategy has been developed to generate α-imino ketones with high regioselectivity. Meanwhile, the method allowed for the preparation of various N,O-ketals with high regioselectivities and diastereoselectivities through cascade reactions in one pot.

Synthesis of quinolines and naphthyridines: Via catalytic retro-aldol reaction of β-hydroxyketones with ortho -aminobenzaldehydes or nicotinaldehydes

A Cu(i)-catalyzed retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes and nicotinaldehydes is reported that produces a range of quinolines and naphthyridines with high efficiency and selectivity. This reaction uses β-hydroxyketones as a regiospecific ketone-protected enolate source via copper-catalyzed retro-aldol Cα-Cβ bond cleavage. The in situ generated copper enolate undergoes kinetically favorable cyclization with ortho-amino aryl aldehydes to produce quinolines and naphthyridines in a chemo- and regioselective manner. The mild and weakly basic reaction conditions also suppress possible side reactions of benzaldehydes under strongly basic conditions, resulting in improved reaction yields.

Intramolecular photoassisted cycloadditions of azaxylylenes and postphotochemical capstone modifications via suzuki coupling provide access to complex polyheterocyclic biaryls

Modular preassembly of azaxylylene photoprecursors, halogen-substituted in the aromatic ring, their intramolecular [4 + 4] or [4 + 2] cycloadditions to tethered unsaturated pendants, and subsequent postphotochemical capstone modification of the primary photoproducts via Suzuki coupling provides rapid access to diverse biaryls of unprecedented topology. This synthetic sequence allows for rapid growth of molecular complexity and is well aligned with methodology of Diversity-Oriented Synthesis.

Design, synthesis, and in vitro pharmacology of new radiolabeled γ-hydroxybutyric acid analogues including photolabile analogues with irreversible binding to the high-affinity γ-hydroxybutyric acid binding sites

γ-Hydroxybutyric acid (GHB) is a psychotropic compound endogenous to the brain. Despite its potential physiological significance, the complete molecular mechanisms of action remain unexplained. To facilitate the isolation and identification of the high-affinity GHB binding site, we herein report the design and synthesis of the first 125I-labeled radioligands in the field, one of which contains a photoaffinity label which enables it to bind irreversibly to the high-affinity GHB binding sites.

A facile synthesis of new 5H-indazolo[3,2-b]benzo[d]-1,3-oxazines via one-pot intramolecular bis-heterocyclizations

(Chemical Equation Presented) The parent 5H-indazolo[3,2-b]benzo[d]-1,3- oxazine heterocycle as well as a series of novel analogues have been synthesized utilizing two subsequent intramolecular heterocyclizations in one pot. A variety of diversity groups were added to explore the scope of this reaction and to provide a number of new compounds for biological screening.

Total synthesis of (-)-martinellic acid

An enantioselective formal total synthesis of the pyrrolo[3,2-c]quinoline natural product martinellic acid has been achieved. The key steps involve a Pd-catalyzed aryl amidation reaction of a pyrroglutamate derivative, an intramolecular [3+2] azomethine ylide-alkene cycloaddition and a reductive ring opening reaction.