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Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2-amino-5-iodobenzoate is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the formation of complex organic molecules that can have therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical sector, Methyl 2-amino-5-iodobenzoate is utilized as an intermediate in the production of various agrochemicals, potentially aiding in the development of substances that can protect crops or enhance their growth.
Used in Dye Industry:
Methyl 2-amino-5-iodobenzoate is also employed in the dye industry, where it serves as an intermediate in the creation of different dyes, contributing to the coloration and properties of these products.
Used in Research and Laboratory Settings:
Methyl 2-amino-5-iodobenzoate is used as a reagent in research and laboratory settings for the synthesis of a variety of organic molecules, facilitating scientific investigations and the development of new chemical entities.

InChI:InChI=1/C8H8INO2/c1-12-8(11)6-4-5(9)2-3-7(6)10/h2-4H,10H2,1H3

Upstream product

• 116027-10-2 5-iodoisatoic anhydride 
• 67-56-1 methanol 
• 118-48-9 isatoic anhydride 
• 5326-47-6 2-amino-5-iodobenzoic acid 
• 74-88-4 methyl iodide 
• 134-20-3 2-carbomethoxyaniline 

Downstream Products

• 119754-20-0 methyl 5-(trimethylsilylethynyl)anthranilate 
• 84646-92-4 Hydrazide of 2-amino-5-iodo-benzoic acid 
• 303030-10-6 4-amino-4'-bromo-biphenyl-3-carboxylic acid methyl ester 
• 485823-73-2 2-(2,4-dichloro-benzoylamino)-5-iodo-benzoic acid methyl ester 
• 390360-79-9 methyl 5-iodo-2-(methylsulfonamido)benzoate 
• 208659-18-1 methyl 2-(N-acetylamino)-5-iodobenzoate 
• 119754-24-4 methyl 2-amino-5-ethynylbenzoate 
• 668261-91-4 methyl 2-amino-5-formylbenzoate 
• 871494-83-6 methyl 2-(acetoacetylamino)-5-iodobenzoate 
• 485824-40-6 methyl 5-iodo-2-[(4-(trifluoromethyl)benzoyl)amino]benzoate 
• 252894-37-4 5-iodo-2-[(4-methoxy-1,4-dioxobutyl)amino]-benzoic acid methyl ester 
• 884196-07-0 2-(3-ethoxycarbonyl-propionylamino)-5-iodo-benzoic acid methyl ester 
• 363185-87-9 methyl 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 
• 871941-68-3 methyl 2-amino-5-[3-(benzyloxy)propyl]benzoate 

Relevant academic research and scientific papers

NCBSI/KI: A Reagent System for Iodination of Aromatics through in Situ Generation of I-Cl

In situ iodine monochloride (I-Cl) generation followed by iodination of aromatics using NCBSI/KI system has been developed. The NCBSI reagent requires no activation due to longer bond length, lower bond dissociation energy, and higher absolute charge density on nitrogen. The system is adequate for mono- and diiodination of a wide range of moderate to highly activated arenes with good yield and purity. Moreover, the precursor N-(benzenesulfonyl)benzenesulfonamide can be recovered and transformed to NCBSI, making the protocol eco-friendly and cost-effective.

Sulfated polyborate-H2O assisted tunable activation of N-iodosuccinimide for expeditious mono and diiodination of arenes

Owing to both Lewis and Bronsted acid active sites on sulfated polyborate under homogenous conditions, we were keen on developing iodination protocol of arenes that can meet the requirement of regioselectivity and higher yield. The sulfated polyborate activates N-iodosuccinimide for mono iodination of highly activated substrates viz. phenols, anilines under anhydrous condition. Water tunes sulfated polyborate to generate more Bronsted acid sites resulting in rapid activation of NIS for diiodination. The protocol was equally applicable to diiodination of 4-hydroxyphenylacetic acid to synthesize 4-hydroxy-3,5-diiodophenylacetic acid, an intermediate of tiratricol, a thyroid treatment drug. This protocol was further integrated via one-pot sequential iodination and Sonogashira coupling to synthesize aryl acetylenes, building blocks for the synthesis of a variety of specialty chemicals, API, and natural products.

METHOD FOR PRODUCING AROMATIC HALOGEN DERIVATIVE

PROBLEM TO BE SOLVED: To provide a highly efficient and economically advantageous method for producing a halogen compound. SOLUTION: The method produces a halogen compound represented by formula (2) (X is a halogen atom, and b is an integer of 1-5) by reacting an aniline derivative represented by formula (1) (R1 is an ester group, a carbonyl group, a nitrile group, a nitro group, an optionally substituted alkyl group or an optionally substituted aralkyl group, and a is an integer of 0-4) with a halogenating agent in the presence of a copper catalyst and a persulfate. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

A novel DMSO-assisted regioselective iodination of aniline analogues

A metal- and oxidant-free electrophilic iodination of aniline analogues was achieved in high to excellent yields at room temperature in MTBE with 0 or 3.5 equivalents of DMSO. Examined substituents include N-alkyl, N,N-dialkyl, N-morpholinyl and N-piperazinyl as well as methyl, Br, CN and CO2CH3 aryl ring substitutions.

Synthesis of functionalized 1,2-diphenylacetylene derivatives

A series of new functionalized 1,2-diphenylacetylene derivatives, including those containing l-prolinamide substituents at the aromatic nuclei, was synthesized using the Sonogashira coupling at the key step.

SELECTIVE ALPHA-7 NICOTINIC RECEPTOR AGONISTS AND METHODS FOR MAKING AND USING THEM

In alternative embodiments, provided are selective agonists having a high affinity for the alpha7 nicotinic acetylcholine receptor (α7 nAChR), assays for selectivity of nicotinic receptor subtype and ligand-gated ion channel subtype based on receptor occupation and response, behavioral assessments for reversing cognitive impairment after scopolamine treatment, enhancing memory retention over time, pharmaceutical compositions and formulations and devices comprising them, and methods for making and using them, including characterizing and efficiently assaying them for receptor subtype selectivity. In alternative embodiments, provided are substituted anti 1,2,3-triazoles compounds with high affinity, and selective binding, for the alpha7 nicotine acetylcholine receptor (α7 nAChR), as exemplified by 5-(1-(2-(Piperidin-1-yl)ethyl)-1H-1,2,3-triazol-4-yl)-1H-indole (“IND1”), 5-((quinuclid-3-yl)-1H-1,2,3-triazol-4-yl)-1H-indole (“IND8”) and 3-(4-hydroxyphenyl-1,2,3-triazol-1-yl) quinuclidine (“QND8”). In alternative embodiments, provided are products of manufacture such as pumps, devices, syringes and the like comprising a compound, pharmaceutical composition or formulation as provided herein.

Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles

A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline. (Figure presented.).

Improved method for microwave-assisted synthesis of benzodiazepine-2,5-diones from isatoic anhydrides mediated by glacial acetic acid

An improved and simpler method for the synthesis of benzodiazepin-2,5-diones and 7-iodobenzodiazepin-2,5-diones catalyzed by glacial acetic acid using isatoic anhydride and 6-iodoisatoic anhydride, respectively, as starting materials is reported. The target products were achieved in good yields (up to 71percent) using microwave irradiation as the activating mode of reaction in the presence of acetic acid instead of the traditional polar aprotic solvents as dimethylformamide (DMF), dimethyl sulfoxide (DMSO) or dimethylacetamide (DMAC). Moreover, relatively simple purification workup is required. The optimal temperature to obtain the benzodiazepin-2,5-dione derivatives was 130 °C, while the best irradiation time was 3 min. In addition, the methodology for the selective preparation of 6-iodoisatoic anhydride with an overall yield of 62percent is presented. Printed in Brazil-

N-hydroxyl heterocycle pyrimindine diketone derivative and preparation method and application thereof

The invention discloses a quinazoline ketone derivative and a preparation method and application thereof.The compound is of the structure as shown in the general formula (I).The invention further relates to a drug composition containing the compound in the formula (I).Activity screening experiments show that the compound has good anti-acne-virus and anti-adenovirus activity, and therefore application of the compound to preparing anti-acne-virus and anti-adenovirus drugs is also provided.Please see the formula (I) in the description.

First discovery of novel 3-hydroxy-quinazoline-2,4(1H,3H)-diones as specific anti-vaccinia and adenovirus agents via ‘privileged scaffold’ refining approach

A series of 1,2,3-triazolyl 3-hydroxy-quinazoline-2,4(1H,3H)-diones was constructed utilizing Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) method. The biological significance of the novel synthesized quinazolines was highlighted by evaluating them in vitro for antiviral activity, wherein several compounds exhibited excellent activity specifically against vaccinia and adenovirus. Especially, 24b11 displayed the most potent inhibitory activity against vaccinia with an EC50value of 1.7 μM, which was 15 fold than that of the reference drug Cidofovir (EC50= 25 μM). 24b13 was the most potent compound against adenovirus-2 with an EC50value of 6.2 μM, which proved lower than all the reference drugs. Preliminary structure–activity relationships were also discussed. To the best of our knowledge, no data are present in the literature on antiviral activity of 3-hydroxy-quinazoline-2,4(1H,3H)-diones against DNA-viruses. Thus, these findings warrant further investigations (library expansion and compound refinement) on this novel class of antiviral agents.