620-05-3

Basic information

• Product Name: BENZYL IODIDE
• Synonyms: BENZYL IODIDE;α-Iodotoluene;IODOMETHYLBENZENE;(iodomethyl)-benzen;alpha-Iodotoluene;benzene,iodomethyl-;Fraissite;Iodophenylmethane
• CAS NO: 620-05-3
• Molecular Formula: C₇H₇I
• Molecular Weight: 218.03
• EINECS: 210-623-1
• Mol File: 620-05-3.mol

Chemical Properties

• Melting Point: 280-282℃
• Boiling Point: 218℃
• Flash Point: 98℃
• Appearance: /
• Density: 1.750
• Vapor Pressure: 0.188mmHg at 25°C
• Refractive Index: 1.6330
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: BENZYL IODIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL IODIDE(620-05-3)
• EPA Substance Registry System: BENZYL IODIDE(620-05-3)

Safety Data

• RIDADR: 2653
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 620-05-3(Hazardous Substances Data)

Usage

Uses

Used in Tear Gas Industry:
BENZYL IODIDE is used as a sensory irritant in the tear gas industry, causing discomfort and irritation to the eyes and respiratory system when inhaled or when it comes into contact with the skin.
Used in Chemical Industry:
BENZYL IODIDE is used as a chemical intermediate in the chemical industry due to its unique properties. It is soluble in alcohol, carbon disulfide, and ether, making it a versatile compound for various chemical reactions and processes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 3667, 1983 DOI: 10.1021/jo00169a010Tetrahedron Letters, 36, p. 609, 1995 DOI: 10.1016/0040-4039(94)02315-3Synthesis, p. 853, 1980 DOI: 10.1055/s-1980-29239

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Look at benzyl chloride, benzyl bromide.

Hazard

Powerful irritant.

Health Hazard

TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

InChI:InChI=1/C7H7I/c8-6-7-4-2-1-3-5-7/h1-5H,6H2

Upstream product

• 64-17-5 ethanol 
• 67-66-3 chloroform 
• 142-96-1 dibutyl ether 
• 4909-77-7 benzyl 2,4,6-trimethylbenzoate 
• 16002-63-4 phenylmagnesium iodide 
• 56463-13-9 1-benzyl-3-methyl-1H-benzimidazol-3-ium iodide 
• 25458-39-3 methylallylbenzylphenylammonium iodide 
• 71-43-2 benzene 
• 98-87-3 benzylidene dichloride 
• 629-45-8 dibutyl disulfide 
• 78985-13-4 (2,3,5,6-tetramethylphenyl)methanol 
• 2154-56-5 benzyl radical 
• 2978-10-1 N,N'-diisopropyl-O-benzyl isourea 
• 13274-43-6 4-methyl-1,2,4-triazoline-3,5-dione 

Downstream Products

• 10316-00-4 4-benzyl-morpholine 
• 15787-39-0 2-benzylisoquinolin-2-ium iodide 
• 56463-13-9 1-benzyl-3-methyl-1H-benzimidazol-3-ium iodide 
• 28386-89-2 2-benzyl-5-phenyl-2H-tetrazole 
• 5441-77-0 2,6-bis-benzylsulfanyl-7⁽⁹⁾H-purine 
• 121238-79-7 N,N-dibenzyl-2-methylpropan-1-amine 
• 20736-40-7 2-(benzyloxy)-1,2-diphenylethanone 
• 6343-54-0 N-benzylformamide 
• 104-57-4 benzyl formate 
• 103-81-1 Benzeneacetamide 
• 140-11-4 Benzyl acetate 

Relevant articles and documents

A novel synthetic route to pentaalkylcyclopentadienylgallium(I) compounds

The reaction of 'GaI' with potassium cyclopentadienides allows a simple access to cyclopentadienylgallium(I)-complexes. Thus, the compounds Me5C5Ga 1 and Me4EtC5Ga 2 have been prepared in high yields. Performing the synthesis of 'GaI' under ultrasonic conditions not in toluene but in benzene as solvent, avoids the formation of benzyl iodide as side product.

Photoinduced Radical Chain Reactions between Alkylcobalt(III) Complexes and Iodide

Cobalt-carbon bonds of various alkylcobalt(III) complexes, cis-ClO4 (R=Me, Et, or PhCH2; bipy = 2,2'-bipyridine), trans->CoMe2(L)> (L=3,9-dimethyl-4,8-diazaundeca-3,8-diene-2,10-dione dioximate), and (R=Me or Et; Hdmg = dimet

Iodine-catalyzed oxidative functionalization of purines with (thio)ethers or methylarenes for the synthesis of purin-8-one analogues

An efficient oxidative functionalization of purine-like substrates with (thio)ethers or methylarenes under mild conditions is described. Using I2as the catalyst, and TBHP as the oxidant, this protocol provides a valuable synthetic tool for the assembly of a wide range of 9-alkyl(benzyl)purin-8-one derivatives with high atom- and step-economy and exceptional functional group tolerance.

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.

Two-Step Protocol for Iodotrimethylsilane-Mediated Deoxy-Functionalization of Alcohols

We have developed a two-step protocol for iodotrimethylsilane-mediated deoxy-functionalization of primary and secondary alcohols to afford products containing a C?N, C?S, or C?O bond. In the first step the alcohol undergoes iodination with iodotrimethylsilane, and in the second, the iodine atom is replaced by a N, S, or O nucleophile. Compared with traditional Mitsunobu reaction, non-acidic pre-nucleophiles can be used, and the reaction proceeds with retention of configuration. This operationally simple, highly efficient protocol can be used for some natural products and small-molecule drugs containing hydroxy-group.

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.

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.

Ligand Free Palladium-Catalyzed Synthesis of α-Trifluoromethylacrylic Acids and Related Acrylates by Three-Component Reaction

Aryl iodides and 2-(trifluoromethyl)acrylic acid reacted together in ligand-free Mizoroki-Heck reaction furnishing a quick and efficient access to highly valuable α-trifluoromethylacrylic acids. The useful transformation was independent with regard to the electronic nature of the aryl group substituent. A three-component one-pot version was also developed to give diverse substituted acrylates. The versatility of α-trifluoromethylacrylic acids was demonstrated by quick access to 3-CF3-coumarins as well as fluorinated analogues of therapeutic or cosmetic agents. Finally, we proposed a catalytic cycle based on the silver carboxylate salt, identified as a key intermediate in the reaction. (Figure presented.).

Discovery of Tyrosine Kinase 2 (TYK2) Inhibitor (PF-06826647) for the Treatment of Autoimmune Diseases

Tyrosine kinase 2 (TYK2) is a member of the JAK kinase family that regulates signal transduction downstream of receptors for the IL-23/IL-12 pathways and type I interferon family, where it pairs with JAK2 or JAK1, respectively. On the basis of human genetic and emerging clinical data, a selective TYK2 inhibitor provides an opportunity to treat autoimmune diseases delivering a potentially differentiated clinical profile compared to currently approved JAK inhibitors. The discovery of an ATP-competitive pyrazolopyrazinyl series of TYK2 inhibitors was accomplished through computational and structurally enabled design starting from a known kinase hinge binding motif. With understanding of PK/PD relationships, a target profile balancing TYK2 potency and selectivity over off-target JAK2 was established. Lead optimization involved modulating potency, selectivity, and ADME properties which led to the identification of the clinical candidate PF-06826647 (22).