348-52-7

Basic information

• Product Name: 1-Fluoro-2-iodobenzene
• Synonyms: 1-fluoro-2-iodo-benzen;O-FLUOROIODOBENZENE;O-IODO FLUOROBENZENE;2-FLUOROIODOBENZENE;1-FLUORO-2-IODOBENZENE;1-fluor-2-oiodobenzene;2-iodofluorobenzene;1-Fluoro-2-iodobenzene,99%
• CAS NO: 348-52-7
• Molecular Formula: C₆H₄FI
• Molecular Weight: 222
• EINECS: 206-477-3
• Product Categories: Aromatic Esters;Fluorobenzene;Miscellaneous;Fluorine Compounds;Iodine Compounds;Aryl;C6;Halogenated Hydrocarbons;Aryl Fluorinated Building Blocks;Building Blocks;Chemical Synthesis;Fluorinated Building Blocks;Halogenated Hydrocarbons;Organic Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks
• Mol File: 348-52-7.mol
• Article Data: 27

Chemical Properties

• Melting Point: −41-−40 °C(lit.)
• Boiling Point: 188-189 °C(lit.)
• Flash Point: 160 °F
• Appearance: Clear light yellow/Liquid
• Density: 1.903 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.791mmHg at 25°C
• Refractive Index: n20/D 1.59(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Sensitive: Light Sensitive
• BRN: 2039770
• CAS DataBase Reference: 1-Fluoro-2-iodobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Fluoro-2-iodobenzene(348-52-7)
• EPA Substance Registry System: 1-Fluoro-2-iodobenzene(348-52-7)

Safety Data

• Hazard Codes: Xn,N,Xi
• Statements: 22-37/38-41-51/53-36/37/38
• Safety Statements: 26-39-61-37/39
• RIDADR: UN3082 - class 9 - PG 3 - DOT NA1993 - Environmentally hazardous
• WGK Germany: 2
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 348-52-7(Hazardous Substances Data)

Usage

Description

1-Fluoro-2-iodobenzene is an organic compound that belongs to the class of aromatic halides. It is a clear, colorless to light yellow liquid with the molecular formula C6H4FI. 1-Fluoro-2-iodobenzene is characterized by the presence of a fluorine atom at the 1st position and an iodine atom at the 2nd position on a benzene ring, which imparts unique chemical properties to the molecule.

Uses

Used in Pharmaceutical Industry:
1-Fluoro-2-iodobenzene is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical properties make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
1-Fluoro-2-iodobenzene is used as a starting material for the synthesis of various organic compounds, including bridged biphenyl compounds, 1-fluoro-8-methylbiphenylene, and 4-fluoro-5-methylfluorene. These compounds have potential applications in various industries, such as materials science and electronics.
Used in Suzuki Reaction:
1-Fluoro-2-iodobenzene is utilized in the Suzuki reaction, a widely used cross-coupling reaction in organic chemistry. This reaction allows for the formation of carbon-carbon bonds, which are essential for the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and advanced materials.
Used in Synthesis of Chiral O-Phosphanophenyl Sulfoxides:
1-Fluoro-2-iodobenzene is also used in the synthesis of chiral o-phosphanophenyl sulfoxides, which are important intermediates in the preparation of various biologically active compounds and pharmaceuticals. These chiral compounds play a crucial role in the development of enantiomerically pure drugs with improved efficacy and reduced side effects.

Synthesis Reference(s)

Synthetic Communications, 20, p. 1701, 1990 DOI: 10.1080/00397919008053092

Upstream product

• 348-54-9 2-Fluoroaniline 
• 462-06-6 fluorobenzene 
• 131049-54-2 o-potassiofluorobenzene 
• 108-95-2 phenol 
• 7647-01-0 hydrogenchloride 
• 56-23-5 tetrachloromethane 
• 7790-99-0 Iodine monochloride 
• 1072-85-1 o-fluorobromobenzene 
• 1993-03-9 o-fluorophenylboronic acid 
• 696-62-8 para-iodoanisole 
• 393-52-2 2-Fluorobenzoyl chloride 
• 615-43-0 2-iodophenylamine 
• 7169-58-6 1-(2-iodophenyl)diazonium tetrafluoroborate 
• 1842-26-8 (2-fluorophenyl)trimethylsilane 

Downstream Products

• 388-82-9 2,2'-difluorobiphenyl 
• 55258-70-3 C₁₄H₁₃FO 
• 36029-96-6 2-fluoro-β,β-difluoro-α-(trifluoromethyl)styrene 
• 3794-15-8 1-benzyl-2-fluorobenzene 
• 312-05-0 2-Fluorphenylphosphonsaeurediethylester 
• 446-49-1 1-ethyl-2-fluorobenzene 
• 104201-65-2 methyl (2E)-3-(2-fluorophenyl)prop-2-enoate 
• 200001-67-8 7-(2-fluorophenyl)-7-norbornanol 
• 217312-98-6 1-(benzyloxy)-5-(2-fluorophenyl)pyrazole 
• 1993-03-9 o-fluorophenylboronic acid 
• 92-52-4 biphenyl 
• 321-60-8 2-fluorobiphenyl 
• 384339-37-1 3-(2-fluorophenyl)-2-(4-methoxybenzyl)pyrazole-1-oxide 
• 362-54-9 2-fluorobenzhydrol 

Relevant articles and documents

Selective C-H Iodination of (Hetero)arenes

Iodoarenes are versatile intermediates and common synthetic targets in organic synthesis. Here, we present a strategy for selective C-H iodination of (hetero)arenes with a broad functional group tolerance. We demonstrate the utility and differentiation to other iodination methods of supposed sulfonyl hypoiodites for a set of carboarenes and heteroarenes.

Functional Group Transposition: A Palladium-Catalyzed Metathesis of Ar-X σ-Bonds and Acid Chloride Synthesis

We describe the development of a new method to use palladium catalysis to form functionalized aromatics: via the metathesis of covalent σ-bonds between Ar-X fragments. This transformation demonstrates the dynamic nature of palladium-based oxidative addition/reductive elimination and offers a straightforward approach to incorporate reactive functional groups into aryl halides through exchange reactions. The reaction has been exploited to assemble acid chlorides without the use of high energy halogenating or toxic reagents and, instead, via the metathesis of aryl iodides with other acid chlorides.

Expanding the Balz–Schiemann Reaction: Organotrifluoroborates Serve as Competent Sources of Fluoride Ion for Fluoro-Dediazoniation

The Balz–Schiemann reaction endures as a method for the preparation of (hetero)aryl fluorides yet is eschewed due to the need for harsh conditions or high temperatures along with the need to isolate potentially explosive diazonium salts. In a departure from these conditions, we show that various organotrifluoroborates (RBF3?s) may serve as fluoride ion sources for solution-phase fluoro-dediazoniation in organic solvents under mild conditions. This methodology was successfully extended to a one-pot process obviating aryl diazonium salt isolation. Sterically hindered (hetero)anilines are fluorinated under unprecedentedly mild conditions in good-to-excellent yields. Taken together, this work expands the repertoire of RBF3?s to act as fluorine ion sources in an update to the classic Balz–Schiemann reaction.