77317-55-6

Basic information

• Product Name: Methyl 2-amino-5-iodobenzoate
• Synonyms: 5-IODOANTHRANILIC ACID METHYL ESTER;2-AMINO-5-IODOBENZOIC ACID METHYL ESTER;METHYL 2-AMINO-5-IODOBENZOATE;METHYL 5-IODOANTHRANILATE;Iodoanthranilicacidmethylester;5-IODOANTHRANILIC ACID METHYL ESTER 98+%;4-Iodo-2-(methoxycarbonyl)aniline, Methyl 5-iodoanthranilate;Benzoic acid, 2-aMino-5-iodo-, Methyl ester
• CAS NO: 77317-55-6
• Molecular Formula: C₈H₈INO₂
• Molecular Weight: 277.06
• EINECS: 1592732-453-0
• Product Categories: Aromatic Esters;Benzoic acid;Acids & Esters;Anilines, Amides & Amines;Iodine Compounds
• Mol File: 77317-55-6.mol
• Article Data: 31

Chemical Properties

• Melting Point: 85 °C
• Boiling Point: 335.9°C at 760 mmHg
• Flash Point: 156.9°C
• Appearance: /
• Density: 1.826g/cm³
• Vapor Pressure: 0.000116mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 1.85±0.10(Predicted)
• CAS DataBase Reference: Methyl 2-amino-5-iodobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-amino-5-iodobenzoate(77317-55-6)
• EPA Substance Registry System: Methyl 2-amino-5-iodobenzoate(77317-55-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 77317-55-6(Hazardous Substances Data)

Usage

General Description

Methyl 2-amino-5-iodobenzoate, also known as 5-Iodoanthranilic acid methyl ester, is a chemical compound with the molecular formula C8H8INO2. It is a white to off-white solid with a molecular weight of 291.06 g/mol. Methyl 2-amino-5-iodobenzoate is used in organic synthesis as an intermediate for the production of pharmaceuticals, agrochemicals, and dyes. It is also employed in research and laboratory settings as a reagent for the synthesis of various organic molecules. Methyl 2-amino-5-iodobenzoate is classified as a hazardous substance and should be handled and stored with proper safety precautions.

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

Upstream product

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

Downstream Products

• 390360-79-9 methyl 5-iodo-2-(methylsulfonamido)benzoate 
• 208659-18-1 methyl 2-(N-acetylamino)-5-iodobenzoate 
• 303030-11-7 4'-bromo-4-iodo-biphenyl-3-carboxylic acid methyl ester 
• 303030-12-8 4-amino-4'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-3-carboxylic acid methyl ester 
• 303030-13-9 4-amino-4'''-bromo-[1,4';1',1'';4'',1''']quaterphenyl-3,2''-dicarboxylic acid dimethyl ester 
• 303030-14-0 4'''-bromo-4-iodo-[1,4';1',1'';4'',1''']quaterphenyl-3,2''-dicarboxylic acid dimethyl ester 
• 303030-15-1 4-amino-4'''-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-[1,4';1',1'';4'',1''']quaterphenyl-3,2''-dicarboxylic acid dimethyl ester 
• 303030-16-2 4-dodecanoylamino-4'''-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-[1,4';1',1'';4'',1''']quaterphenyl-3,2''-dicarboxylic acid dimethyl ester 
• 363185-87-9 methyl 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 
• 1005029-94-6 2-(4'-iodo-2'-(methoxycarbonyl)phenylamino)benzoic acid 
• 871941-68-3 methyl 2-amino-5-[3-(benzyloxy)propyl]benzoate 
• 1449228-40-3 senexin B 
• 1449228-17-4 C₂₆H₂₆IN₅O 
• 132533-57-4 3,4-dihydro-3-hydroxy-6-iodo-4-oxo-1,2,3-benzotriazine 

Relevant articles and documents

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.

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

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.