111771-08-5

Basic information

• Product Name: 2-FLUORO-6-IODOBENZOIC ACID
• Synonyms: RARECHEM AL BO 0280;TIMTEC-BB SBB006699;2-FLUORO-6-IODOBENZOIC ACID;2-Fluoro-6-iodobenzoic;2-Fluoro-6-iodobenzoic acid 98%;2-Fluoro-6-iodobenzoicacid98%;2-Fluoro-6-iodobenzoic acid, 98% 1GR
• CAS NO: 111771-08-5
• Molecular Formula: C₇H₄FIO₂
• Molecular Weight: 266.01
• Product Categories: C7;Carbonyl Compounds;Carboxylic Acids;Fluorine series
• Mol File: 111771-08-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 123-126 °C(lit.)
• Boiling Point: 301.556 °C at 760 mmHg
• Flash Point: 136.176 °C
• Appearance: Yellow to light brown/Powder
• Density: 1.9575 (estimate)
• Vapor Pressure: 0.000463mmHg at 25°C
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 1.93±0.10(Predicted)
• Sensitive: Light Sensitive
• BRN: 4982371
• CAS DataBase Reference: 2-FLUORO-6-IODOBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-FLUORO-6-IODOBENZOIC ACID(111771-08-5)
• EPA Substance Registry System: 2-FLUORO-6-IODOBENZOIC ACID(111771-08-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 111771-08-5(Hazardous Substances Data)

Usage

Description

2-Fluoro-6-iodobenzoic acid is a chemical compound characterized by the presence of a fluorine atom at the 2nd position and an iodine atom at the 6th position on a benzoic acid backbone. It is a loose white crystal that can be synthesized using 2-amino-6-fluorobenzoic acid as the starting material. 2-FLUORO-6-IODOBENZOIC ACID exhibits yellow to light brown powder as its chemical properties.

Uses

Used in Pharmaceutical Industry:
2-Fluoro-6-iodobenzoic acid is used as a key intermediate in the synthesis of fluoro-substituted benzoyl chlorides, which are important building blocks for the development of pharmaceutical compounds. These benzoyl chlorides can be utilized in the creation of various drug molecules, potentially enhancing their properties and effectiveness.
Used in Organic Chemistry:
2-Fluoro-6-iodobenzoic acid is employed as a starting material for the one-pot regioselective synthesis of isocoumarins. Isocoumarins are a class of organic compounds with diverse applications, including as pharmaceutical agents, agrochemicals, and synthetic intermediates. The regioselective synthesis of isocoumarins from 2-fluoro-6-iodobenzoic acid allows for the efficient production of these valuable compounds.

InChI:InChI=1/C7H4FIO2/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3H,(H,10,11)/p-1

Upstream product

• 124-38-9 carbon dioxide 
• 1121-86-4 1-Fluoro-3-iodobenzene 
• 372-19-0 meta-fluoroaniline 
• 445-29-4 o-fluoro-benzoic acid 
• 851368-08-6 1-bromo-2-fluoro-6-iodobenzene 

Downstream Products

• 1050203-43-4 N-allyl-N-benzyl-2-fluoro-6-iodobenzamide 
• 1105701-46-9 N-allyl-6-fluoro-2-iodo-N-methylbenzamide 
• 1105701-45-8 N,N-diallyl-6-fluoro-2-iodobenzamide 
• 1262193-14-5 (2,4,6-trimethylbenzene-1,3,5-triyl)tris(methylene) tris(2-fluoro-6-iodobenzoate) 
• 146137-72-6 6-fluoro-2-iodobenzaldehyde 
• 1050203-52-5 1-chloro-8-fluoro-4-methylisoquinoline 
• 1050203-46-7 1-bromo-8-fluoro-4-methylisoquinoline 
• 1231747-49-1 2-(bromomethyl)-1-fluoro-3-iodobenzene 
• 42899-84-3 3-fluoro-N-phenylphthalimide 

Relevant articles and documents

Base- and Additive-Free Ir-Catalyzed ortho-Iodination of Benzoic Acids: Scope and Mechanistic Investigations

A protocol for the C-H activation/iodination of benzoic acids catalyzed by a simple iridium complex has been developed. The method described in this paper allows the ortho-selective iodination of a variety of benzoic acids under extraordinarily mild conditions in the absence of any additive or base in 1,1,1,3,3,3-hexafluoroisopropanol as the solvent. The iridium catalyst used tolerates air and moisture, and selectively gives ortho-iodobenzoic acids with high conversions. Mechanistic investigations revealed that an Ir(III)/Ir(V) catalytic cycle operates, and that the unique properties of HFIP enables the C-H iodination using the carboxylic moiety as a directing group.

PdII-catalyzed monoselective ortho halogenation of C-H bonds assisted by counter cations: A complementary method to directed ortho lithiation

(Chemical Equation Presented) When the counterion counts: The yield and selectivity of the title transformation of benzoic acid derivatives were improved greatly by using tetraalkyl ammonium salts as additives (see scheme; monoselectivity: 5:1-18:1). These effects are attributed to the influence of counter cations. The halogenated products are versatile intermediates for the construction of substituted aromatic compounds. DMF=N,N-dimethylformamide.

Promoting or preventing haloaryllithium isomerizations: Differential basicities and solvent effects as the crucial variables

Deprotonation-triggered heavy halogen migrations should become a favorite tool in arene synthesis if their occurrence and outcome could be made predictable. Particularly attractive, though extremely rare, are stop-and-go situations where a first intermediate, generated by metalation, can be trapped at -100 °C, whereas at -75 °C halogen migration gives rise to an isomer. As shown now, one can conveniently produce the initial aryllithium species by halogen/metal interconversion in toluene at -100 °C, under conditions that preclude, halogen migration, and unleash the isomerization process by adding tetrahydrofuran at -75 °C.