625-99-0

Basic information

• Product Name: 1-Chloro-3-iodobenzene
• Synonyms: 1-chloro-3-iodo-benzen;3-Chloro-1-iodobenzene;3-Iodochlorobenzene;m-Chlorophenyl iodide;M-CHLOROIODOBENZENE;3-CHLOROIODOBENZENE;1-CHLORO-3-IODOBENZENE;M-IODOCHLOROBENZENE
• CAS NO: 625-99-0
• Molecular Formula: C₆H₄ClI
• Molecular Weight: 238.45
• EINECS: 210-920-6
• Product Categories: Aromatic Halides (substituted);Chlorine Compounds;Iodine Compounds;Aryl;C6;Halogenated Hydrocarbons;alkyl Iodine| alkyl chloride
• Mol File: 625-99-0.mol

Chemical Properties

• Melting Point: 95-96 °C
• Boiling Point: 103-104 °C15 mm Hg(lit.)
• Flash Point: 215 °F
• Appearance: Clear light yellow/Liquid
• Density: 1.926 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.102mmHg at 25°C
• Refractive Index: n20/D 1.631(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility: Soluble in water 67.2 mg/L.
• Sensitive: Light Sensitive
• BRN: 1904539
• CAS DataBase Reference: 1-Chloro-3-iodobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Chloro-3-iodobenzene(625-99-0)
• EPA Substance Registry System: 1-Chloro-3-iodobenzene(625-99-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 625-99-0(Hazardous Substances Data)

Usage

Chemical Properties

Clear light yellow liquid

Uses

Different sources of media describe the Uses of 625-99-0 differently. You can refer to the following data:
1. suzuki reaction
2. 1-Chloro-3-iodobenzene is used as a pharmaceutical intermediate.

Synthesis Reference(s)

Synthetic Communications, 11, p. 639, 1981 DOI: 10.1080/00397918108063637

General Description

The multiple-quantum proton NMR spectra of 3-chloroiodobenzene was studied.

Upstream product

• 108-42-9 3-chloro-aniline 
• 626-01-7 3-Iodoaniline 
• 31928-46-8 2-bromo-1-chloro-4-iodobenzene 
• 4405-42-9 m-chlorophenyltrimethylsilane 
• 201230-82-2 carbon monoxide 
• 16825-75-5 1-iodyl-3-chlorobenzene 
• 150177-91-6 3-bromo-1-iodylbenzene 
• 456-39-3 3-chlorobenzenediazonium tetrafluoroborate 
• 108-90-7 chlorobenzene 
• 108-95-2 phenol 
• 16308-17-1 (3-chlorophenyl)iodanediyl diacetate 
• 50-81-7 ascorbic acid 
• 10034-85-2 hydrogen iodide 
• 100-77-6 3-chlorobenzenediazonium chloride 

Downstream Products

• 535-80-8 3-chlorobenzoate 
• 958-96-3 3,3'-dinitro-1,1'-biphenyl 
• 952-04-5 3-chloro-3'-nitro-biphenyl 
• 6452-49-9 1-chloro-3-phenoxybenzene 
• 16308-17-1 (3-chlorophenyl)iodanediyl diacetate 
• 53595-98-5 (3-chloro-phenyl)-(4-methoxy-phenyl)-amine 
• 63503-60-6 3-chlorophenylboronic acid 
• 30101-12-3 (3-chlorophenyl)diiodoborane 
• 51624-34-1 1-chloro-3-(2-phenylethynyl)benzene 
• 127257-58-3 1-(3-chlorophenyl)-3-phenylisobenzofuran 
• 122961-10-8 1-chloro-3-(3,3,3-trifluoroprop-1-ynyl)benzene 
• 2974-10-9 1,3-bis(phenylthio)benzene 
• 587-04-2 m-Chlorobenzaldehyde 
• 7094-34-0 bis(3-chlorophenyl)methanone 

Relevant articles and documents

Synthesis of biaryl compounds via Suzuki homocoupling reactions catalyzed by metal organic frameworks encapsulated with palladium nanoparticles

Heterogeneous homocoupling reactions of phenylboronic acids were greatly accelerated via Suzuki homocoupling reactions. In this work, a tandem route was designed which firstly one part of phenylboronic acids reacted with iodine to form iodobenzenes, then another part of phenylboronic acids coupled with iodobenzenes to produce biaryl compounds. The tandem reaction were catalyzed by a bifunctional heterogeneous catalyst of metal organic frameworks encapsulated with palladium nanoparticles (Pd?MOFs). This strategy for forming symmetric C-C bond between benzene rings has obvious advantages such as high efficiency, easy separation, good recyclability and no addition of toxic halogenated benzene.

An efficient gram scale synthesis of aryl iodides from aryl diazofluoroborates in water under mild conditions

Transition metal-free synthesis of synthetically valuable aryl iodides from aryl diazofluroborates in water under mild conditions has been described. Majority of synthesized aryl iodides are obtained in quantitative yields (>99%) under present reaction conditions. The structural effects due to the substituents present on aryl diazofluoroborates did not show any satisfactory effect on the yields of the aryl iodides. Hence, the methodology presented here was found to be adventitious for the quantitative production of synthetically valuable aryl iodides.

Visible-Light-Induced Decarboxylative Iodination of Aromatic Carboxylic Acids

A convenient, efficient and practical visible-light-induced decarboxylative iodination of aromatic carboxylic acids has been developed, and the corresponding aryl iodides were obtained in good yields. The method shows some advantages including the use of readily available aromatic carboxylic acids as the starting materials, simple and mild conditions, high efficiency, wide substrate scope and tolerance of various functional groups.

Compartmentalization of incompatible reagents within Pickering emulsion droplets for one-pot cascade reactions

It is a dream that future synthetic chemistry can mimic living systems to process multistep cascade reactions in a one-pot fashion. One of the key challenges is the mutual destruction of incompatible or opposing reagents, for example, acid and base, oxidants and reductants. A conceptually novel strategy is developed here to address this challenge. This strategy is based on a layered Pickering emulsion system, which is obtained through lamination of Pickering emulsions. In this working Pickering emulsion, the dispersed phase can separately compartmentalize the incompatible reagents to avoid their mutual destruction, while the continuous phase allows other reagent molecules to diffuse freely to access the compartmentalized reagents for chemical reactions. The compartmentalization effects and molecular transport ability of the Pickering emulsion were investigated. The deacetalization-reduction, deacetalization-Knoevenagel, deacetalization-Henry and diazotization-iodization cascade reactions demonstrate well the versatility and flexibility of our strategy in processing the one-pot cascade reactions involving mutually destructive reagents. (Figure Presented).

Practical and efficient ipso-iodination of arylboronic acids via KF/I2 system

A facile and effective iododeboronation of variously substituted aryl and heteroarylboronic acids through activation and subsequent ipso-introduction of iodine is presented. The use of KF and I2 at 80 °C in 1,4-dioxane furnishes iodinated compounds in high yields.

PROCESS FOR THE PREPARATION OF N-IODOAMIDES

The present invention provides new stable crystalline N-iodoamides - 1-iodo- 3,5,5-trimethylhydantoin (1-ITMH) and 3-iodo-4,4-dimethyl-2-oxazolidinone (IDMO). The present invention further provides a process for the preparation of organic iodides using N-iodoamides of this invention and recovery of the amide co-products from waste water.

Metal-free iodination of arylboronic acids and the synthesis of biaryl derivatives

A simple, general and efficient method is developed for the metal-free iodination of arylboronic acids. The protocol uses very cheap molecular iodine as the halide source and potassium carbonate as the base. The method is highly tolerant of various functional groups present in the substrates. Importantly, the iodination strategy can also be applied very effectively in the one-pot, two-step synthesis of biaryl derivatives. Georg Thieme Verlag Stuttgart New York.

Synthesis and structure-activity relationship of 5-substituent-2(1H)- pyridone derivatives as anti-fibrosis agents

Pyridone compounds, such as pirfenidone (PFD) and fluorofenidone (AKF-PD), are multi-target anti-fibrotic agents. Using PFD and AKF-PD as the leading compounds, two series of novel (5-substituent)-2(1H)-pyridone compounds were synthesized with the purpose of maintaining multi-targeting property and overcoming the drawbacks of fast metabolism. These derivatives demonstrated good proliferation inhibiting activity against NIH3T3 cells by MTT assay with AKF-PD as the positive control. Compound 5b exhibited a high potent of anti-fibrosis with a IC50 of 0.08 mmol/L about 34 times of AKF-PD. The SAR of pyridone derivatives as anti-fibrosis agents was also discussed.

PROCESS FOR THE PREPARATION OF IODIDES

This invention is directed to a process for the preparation of high yield alkyl or aryl iodide from its corresponding carboxylic acid using N-iodo amides.

General copper-catalyzed transformations of functional groups from arylboronic acids in water

A simple and general copper-catalyzed method has been developed for transformations of various functional groups (i I, i N3, i SO2R, i OH, i NH2, and i NO 2) on aromatic rings from arylboronic acids in water under air. The protocol uses cheap and readily available inorganic salts (KI, NaN3, NaSO2R, NaOH, NaNO2) and aqueous ammonia as the functional-group sources, simple Cu2O/NH3 as the catalyst system, environmentally friendly water as the solvent, and oxygen in air as the oxidant. Importantly, the copper catalyst system in water was recyclable. This study should provide a useful strategy for interconversions of the functional groups on aromatic rings.