35424-56-7

Usage

Uses

Used in Pharmaceutical Industry:
1-chloro-4-(iodomethyl)benzene is used as a synthetic intermediate for the development of various pharmaceuticals. Its unique structure allows for the creation of a wide range of medicinal compounds, contributing to the advancement of treatments for different health conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 1-chloro-4-(iodomethyl)benzene is utilized as a precursor in the synthesis of pesticides and other crop protection agents. Its involvement in the production of these chemicals helps to ensure the protection and yield of agricultural products.
Used in Dyes and Pigments Industry:
1-chloro-4-(iodomethyl)benzene is employed as a key component in the manufacturing process of dyes and pigments. Its chemical properties make it suitable for the production of colorants used in various industries, including textiles, plastics, and printing inks.
Used in Organic Synthesis:
As a versatile building block in organic synthesis, 1-chloro-4-(iodomethyl)benzene is used for the preparation of a variety of fine chemicals. Its reactivity and structural features facilitate the synthesis of complex organic molecules for use in research and commercial applications.

Upstream product

• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 76950-79-3 1-(4-Chloro-benzyl)-2-methylsulfanyl-4,6-diphenyl-pyridinium; iodide 
• 873-76-7 para-Chlorobenzyl alcohol 
• 10034-85-2 hydrogen iodide 
• 64-19-7 acetic acid 
• 622-95-7 4-chlorobenzyl bromide 
• 1950-78-3 p-toluenesulfonyl iodide 
• 14856-74-7 4-chlorobenzyltrimethylsilyl ether 
• 95458-82-5 diethyl 4-chlorobenzyl phosphate 
• 74-11-3 para-chlorobenzoic acid 
• 1202-68-2 4-chloro-1-[(ethoxymethoxy)methyl]benzene 
• 1200-16-4 1-chloro-4-[(methoxymethoxy)methyl]benzene 
• 106-43-4 para-chlorotoluene 
• 104-86-9 4-chlorobenzylamine 

Downstream Products

• 109099-54-9 1-(4-chloro-benzyl)-tetrahydro-thiophenium; iodide 
• 13616-25-6 1,6-bis-(4-chloro-benzylsulfanyl)-[1,4]dithiino[2,3-d;5,6-d']dipyridazine 
• 61734-33-6 C₁₂H₁₅Cl₂NO₃ 
• 131890-34-1 2-(4-Chloro-benzylsulfanyl)-4-(3-methoxy-phenyl)-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile 
• 142590-01-0 5-Chloro-3-(4-chloro-benzyl)-1-{[1-phenyl-meth-(E)-ylidene]-amino}-1H-pyrimidine-2,4-dione 
• 142590-07-6 5-Bromo-3-(4-chloro-benzyl)-1-{[1-phenyl-meth-(E)-ylidene]-amino}-1H-pyrimidine-2,4-dione 
• 106-43-4 para-chlorotoluene 
• 6258-66-8 (4-chlorophenyl)methanethiol 
• 150109-58-3 1-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(4-chloro-benzyloxy)-tetrahydro-furan-2-yl]-5-fluoro-1H-pyrimidine-2,4-dione 
• 1054633-48-5 1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-chloro-benzyloxymethyl)-tetrahydro-furan-2-yl]-5-fluoro-1H-pyrimidine-2,4-dione 
• 1026729-45-2 methyl (2E)-2-benzylidene-4-(4-chlorophenyl)butanoate 
• 1026729-41-8 methyl (2E)-2-(4-chlorobenzylidene)-4-(4-chlorophenyl)butanoate 
• 619-56-7 4-chlorobenzamide 
• 16264-03-2 1-(4-chloro-benzyl)-4-(4-nitro-phenyl)-piperazine 

Relevant academic research and scientific papers

Iminophosphorane-mediated regioselective umpolung alkylation reaction of α-iminoesters

Umpolung reactions of imines, especially the asymmetric reactions, have been extensively studied as they provide access to important chiral amines in an efficient manner. The reactions studied range from simple Michael reactions to several kinds of other reactions such as the aza-benzoin reaction, aza-Stetter reaction, addition with MBH carbonate, and Ir-catalysed allylation. Herein, we report the first umpolung alkylation reaction of α-iminoesters with alkyl halides mediated by iminophosphorane as an organic superbase. The desired products were obtained in up to 82% yield with almost perfect regioselectivities. The key to the regioselectivity of this reaction was the use of 4-trifluoromethyl benzyl imines as a substrate. The products were successfully derivatised into the more functionalised molecules in good yields.

Conversion of Aryl Aldehydes to Benzyl Iodides and Diarylmethanes by H3PO3/I2

For the first time, H3PO3 was used as both the reducing reagent and the promotor in the reductive benzylation reactions with aryl aldehydes. By using a H3PO3/I2 combination, various aromatic aldehydes underwent iodination reactions and Friedel-Crafts type reactions with arenes via benzyl iodide intermediates, readily producing benzyl iodides and diarylmethanes in good yields. Intramolecular cyclization reactions also took place, giving the corresponding cyclic compounds. This new strategy features easy-handling, low-cost, and metal-free conditions.

Preparation method of benzyl iodide and derivatives thereof

The invention discloses a preparation method of benzyl iodide and derivatives thereof, which comprises the following steps: in a protective atmosphere, carrying out heating reaction on aryl aldehyde and iodine elementary substance in the presence of a solvent and phosphorous acid to obtain benzyl iodide and derivatives thereof. According to the method, cheap and green solid phosphorous acid is selected as a reduction reagent for reaction, elemental iodine is selected as an iodine source, the benzyl iodide and the derivatives thereof are efficiently prepared from the aryl aldehyde compounds which are simple and easy to obtain by a one-pot one-step method under mild conditions, and the method has the advantages of simplicity in operation, cheap and easily available reagents, environmental friendliness and the like; and the use of expensive silicon-hydrogen compounds and transition metal catalysts is avoided, and the yield can reach 94% at most, so that the method is beneficial to industrial production.

Method for preparing benzyl iodide and derivatives thereof

The invention discloses a method for efficiently preparing benzyl iodide and derivatives thereof. The preparation method is characterized in that a benzyl alcohol compound, iodine and hydrogen are used as the reaction raw materials and rhodium and phosphine ligand are used as the catalyst to perform one-step reaction in an organic solvent under a positive pressure condition to synthesize the target benzyl iodide and the derivatives thereof, and the reaction formula of the reaction is as shown in the specification. The method has the advantages that the iodination of the method can be easily achieved, reaction condition requirements are low, large-scale industrial production can be achieved, the yield of the benzyl iodide can reach 82% or above, and the yield of the derivatives of the benzyl iodide can reach 99% or above; the method is wide in application range, short in process flow, low in raw material cost and applicable to the industrial production of a series of benzyl iodide and the derivatives thereof.

Preparation method of benzyl iodide and derivatives thereof

The invention discloses a preparation method of benzyl iodide and derivatives thereof. The preparation method comprises the following steps: under the reduction action of sodium borohydride, a benzylalcohol compound shown as a formula I reacts with elemental iodine to obtain benzyl iodide shown as a formula II and derivatives thereof; in the formula I and the formula II, R represents one or moresubstituents on a benzene ring and is selected from at least one of aryl, substituted or unsubstituted alkyl, halogen and nitro. The preparation method of benzyl iodide and derivatives thereof is scientific and reasonable, sodium borohydride which is mild in reactivity, low in price and easily available is used as a reducing agent, and elemental iodine is convenient and easily available; in addition, the preparation method has the characteristics of simplicity and convenience in operation, high synthesis yield, easiness in product purification, environmental friendliness and the like.

Method for efficiently preparing benzyl iodide and derivatives thereof

The invention discloses a method for efficiently preparing benzyl iodide and derivatives thereof. The benzyl iodide and the derivatives thereof are prepared by using a benzaldehyde compound as the initial raw material through complex reaction, main reaction and post-reaction. The method specifically includes: placing rhodium and phosphine ligand into a reaction container, adding an organic solvent, stirring for complexing to obtain a reaction system a, adding iodine, stirring under room temperature, adding the initial material benzaldehyde compound to continuously perform stirring reaction toobtain reaction liquid b, transferring into a high-pressure reaction kettle, performing gas replacement, filling hydrogen, keeping positive pressure, performing reaction under room temperature for 4-48 hours to obtain reaction liquid c, and performing vacuum concentration and column chromatography purification to obtain the target benzyl iodide and the derivatives thereof. The method is cheap in used substrate, simple to operate, good in reaction operation safety, environmentally friendly, high in yield, high in the purity of the benzyl iodide and the derivatives thereof, easy to achieve large-scale production and capable of achieving industrial production to satisfy social medical requirements.

A new HPLC-UV derivatization approach for the determination of potential genotoxic benzyl halides in drug substances

Benzyl halides, widely used as alkylation reagents in drug synthesis, are potential genotoxic impurities (PGTIs) required to be controlled at trace levels. However, the existing analytical methods for benzyl halides often suffer from matrix interferences or low derivatization efficiency of benzyl chlorides. In this paper, a simple derivatization HPLC-UV method was developed for the analysis of these residual trace benzyl halides in drug substances. 1-(4-Nitrophenyl) piperazine (4-NPP) was selected as a new derivatization reagent because it shifted well the benzyl halides derivatives away to the near visible range (392 nm), which could minimize the matrix interferences from the drug substances and related impurities. Meanwhile, potassium iodide (KI) was used to convert the mixed benzyl halides into benzyl iodides before derivatization. The derivatization parameters were also optimized using the design of experiments (DoE) for achieving the best reaction efficiency. The results showed that the new approach had high specificity and sensitivity, and the LOQs were 7-9 μg g-1 relative to 5 mg mL-1 antipyrine and 17.5-22.5 μg g-1 relative to 2 mg mL-1 oroxylin A. The method is a valuable alternative for the determination of residual benzyl halides in the drug substances.

Synthesis of Alkyl Halides from Aldehydes via Deformylative Halogenation

An unprecedented deformylative halogenation of aldehydes to alkyl halides is presented. Under oxidative conditions, 1,4-dihydropyridine (DHP), derived from an aldehyde, generated a C(sp3)- radical that coupled with a halogen radical that was generated from inexpensive and atom-economical halogen sources (NaBr, NaI, or HCl), to yield an alkyl halide. Because of the mild conditions, a wide range of functional groups were tolerated, and excellent site selectivity was achieved.

Rhodium-Catalyzed Generation of Anhydrous Hydrogen Iodide: An Effective Method for the Preparation of Iodoalkanes

The preparation of anhydrous hydrogen iodide directly from molecular hydrogen and iodine using a rhodium catalyst is reported for the first time. The anhydrous hydrogen iodide generated was proven to be highly active in the transformations of alkenes, phenyl aldehydes, alcohols, and cyclic ethers to the corresponding iodoalkanes. Therefore, the present methodology not only has provided convenient access to anhydrous hydrogen iodide but also offers a practical preparation method for various iodoalkanes in excellent atom economy.

N-Hydroxyphthalimide-Mediated Electrochemical Iodination of Methylarenes and Comparison to Electron-Transfer-Initiated C-H Functionalization

An electrochemical method has been developed for selective benzylic iodination of methylarenes. The reactions feature the first use of N-hydroxyphthalimide as an electrochemical mediator for C-H oxidation to nonoxygenated products. The method provides the basis for direct (in situ) or sequential benzylation of diverse nucleophiles using methylarenes as the alkylating agent. The hydrogen-atom transfer mechanism for C-H iodination allows C-H oxidation to proceed with minimal dependence on the substrate electronic properties and at electrode potentials 0.5-1.2 V lower than that of direct electrochemical C-H oxidation.