93415-79-3

Basic information

• Product Name: METHYL 2-IODO-3-NITROBENZOATE
• Synonyms: SPECS AI-942/25034494;2-IODO-3-NITROBENZOIC ACID METHYL ESTER;METHYL 2-IODO-3-NITROBENZOATE;2-Iodo-3-(methoxycarbonyl)nitrobenzene
• CAS NO: 93415-79-3
• Molecular Formula: C₈H₆INO₄
• Molecular Weight: 307.04
• Mol File: 93415-79-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 61 °C
• Boiling Point: 342.1°Cat760mmHg
• Flash Point: 160.7°C
• Appearance: /
• Density: 1.904g/cm³
• Vapor Pressure: 7.7E-05mmHg at 25°C
• Refractive Index: 1.631
• CAS DataBase Reference: METHYL 2-IODO-3-NITROBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2-IODO-3-NITROBENZOATE(93415-79-3)
• EPA Substance Registry System: METHYL 2-IODO-3-NITROBENZOATE(93415-79-3)

Safety Data

• Hazardous Substances Data: 93415-79-3(Hazardous Substances Data)

Usage

General Description

Methyl 2-iodo-3-nitrobenzoate is a chemical compound with the molecular formula C8H6INO4. It is a nitrobenzoate ester, containing an iodine atom and a nitro group. METHYL 2-IODO-3-NITROBENZOATE is commonly used as a reagent in organic synthesis for the preparation of various pharmaceuticals, agrochemicals, and other fine chemicals. It is also utilized as an intermediate in the production of dyes and pigments. Methyl 2-iodo-3-nitrobenzoate is known for its high reactivity and it is important for researchers in the field of organic chemistry.

InChI:InChI=1/C8H6INO4/c1-14-8(11)5-3-2-4-6(7(5)9)10(12)13/h2-4H,1H3

Upstream product

• 67-56-1 methanol 
• 88-67-5 2-Iodobenzoic acid 
• 5398-69-6 2-iodo-3-nitrobenzoic acid 
• 95067-27-9 2-acetylamino-3-nitro-benzoic acid methyl ester 
• 134-20-3 2-carbomethoxyaniline 
• 603-11-2 3-nitrophthalic acid 
• 7647-01-0 hydrogenchloride 
• 856789-07-6 bis-(2-methoxycarbonyl-6-nitro-phenyl)-mercury 

Downstream Products

• 93415-85-1 N-(2'-Carbomethoxy-6'-nitrophenyl)-5-amino-4-carbomethoxy-6-nitro-1,3-benzdioxol 
• 1597416-57-3 (S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-iodobenzoate 
• 1597416-58-4 (S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-((trimethylsilyl)ethynyl)benzoate 
• 1613384-13-6 C₃₂H₃₈N₄O₁₀ 
• 1597416-59-5 (S)-methyl 3-(2-((tert-butoxycarbonyl)amino)propanamido)-2-ethynylbenzoate 
• 1597416-60-8 (S)-dimethyl 2,2'-(ethyne-1,2-diyl)bis(3-((S)-2-((tert-butoxycarbonyl)amino)propanamido)benzoate) 
• 1597416-61-9 di-tert-butyl ((2S,2'S)-(((S)-ethyne-1,2-diylbis(3-(((S)-1-(isobutylamino)-1-oxopropan-2-yl)carbamoyl)-2,1-phenylene))bis(azanediyl))bis(1-oxopropane-2,1-diyl))dicarbamate 
• 1597416-62-0 tert-butyl ((S)-1-((2-iodo-3-(((S)-1-(isobutylamino)-1-oxopropan-2-yl)carbamoyl)phenyl)amino)-1-oxopropan-2-yl)carbamate 
• 1597416-63-1 (S)-2,2'-(ethyne-1,2-diyl)bis(3-((S)-2-acetamidopropanamido)-N-((S)-1-(isobutylamino)-1-oxopropan-2-yl)benzamide) 
• 283173-79-5 2-(4-chloro-phenyl)-3-formyl-1H-indole-4-carboxylic acid methyl ester 
• 283173-78-4 2-(4-Chloro-phenyl)-1H-indole-4-carboxylic Acid Methyl Ester 

Relevant articles and documents

A photoredox-neutral Smiles rearrangement of 2-aryloxybenzoic acids

We report on the use of visible light photoredox catalysis for the radical Smiles rearrangement of 2-aryloxybenzoic acids to obtain aryl salicylates. The method is free of noble metals and operationally simple and the reaction can be run under mild batch or flow conditions. Being a redox neutral process, no stoichiometric oxidants or reductants are needed.

5-Nitroisocoumarins from tandem Castro-Stephens coupling-6-endo-dig cyclisation of 2-iodo-3-nitrobenzoic acid and arylethynes and ring-closure of methyl 2-alkynyl-3-nitrobenzoates with electrophiles

Reaction of 2-iodo-3-nitrobenzoic acid with arylalkynyl copper(I) reagent gave 3-aryl-5-nitroisocoumarins. Castro-Stephens coupling was followed by in situ Cu-catalysed ring-closure. 1H NMR and X-ray crystallography showed the cyclisations to be 6-endo, contrasting with reports of 5-exo cyclisation of analogous 2-iodobenzoate esters with alkynes. Sonogashira couplings of methyl 2-iodo-3-nitrobenzoate with phenylacetylene and with trimethylsilylacetylene gave the corresponding 2-alkynyl-3-nitrobenzoate esters. With HgSO4, the phenylalkyne underwent 6-endo cyclisation to give 5-nitro-3-phenylisocoumarin. The disubstituted alkyne esters gave 4-phenylselenylisocoumarins with PhSeCl. 5-Nitro-3-phenyl-4-phenylselenylisocoumarin shows significant sterically-driven distortion of the isocoumarin ring. Reaction of methyl 3-nitro-2-phenylethynylbenzoate with ICl gave the 4-iodoisocoumarin. Thus the nitro group tends to direct these electrophile-driven cyclisations towards the 6-endo mode.

A new synthesis of 'push-pull' naphthalenes by condensation of nitro-2-methylbenzoate esters with dimethylacetamide dimethyl acetal

Whereas condensation of 2-methyl-3-nitrobenzoate esters with dimethylformamide dimethyl acetal gives 5-nitroisocoumarin, analogous condensation with dimethylacetamide dimethyl acetal proceeds via a different route, affording 1-methoxy-3-dimethylamino-5-ni