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 
• 4563-33-1 phenyl-methanesulfonic acid amide 
• 173165-16-7 3,6-bis-benzyloxy-2,5-dihydro-pyrazine 
• 74-88-4 methyl iodide 
• 56463-13-9 1-benzyl-3-methyl-1H-benzimidazol-3-ium iodide 
• 103200-08-4 S-Benzyl-S-methyl iminodithiocarbonate hydroiodide 
• 108-24-7 acetic anhydride 
• 100-39-0 benzyl bromide 
• 7596-28-3 1-benzyl-1-methyl-piperidinium; iodide 
• 100-44-7 benzyl chloride 

Downstream Products

• 10316-00-4 4-benzyl-morpholine 
• 2116-65-6 4-benzyl pyridine 
• 101-82-6 2-Benzylpyridine 
• 620-95-1 3-benzylpyridine 
• 46210-32-6 1-benzylpyridin-1-ium iodide 
• 74332-95-9 4-benzylsulfanyl-2,6-dimethyl-pyrylium; iodide 
• 15787-39-0 2-benzylisoquinolin-2-ium iodide 
• 43120-26-9 2-benzyl-2H-indazole 
• 56463-13-9 1-benzyl-3-methyl-1H-benzimidazol-3-ium iodide 

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

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.

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.

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.

Cuprous complex containing diphospho-ortho-carborane ligand as well as preparation method and application thereof (by machine translation)

The method comprises the following steps, adding :1) solution to the ortho-carborane solution n - BuLi, reacting, at room temperature for 30 - 60min;2), adding, and reacting 1 - 3h;3) with high yield CuI, of the monovalent copper complex to react alcohol and iodide to synthesize the iodo-hydrocarbon 3 - 6h, and synthesizing the iodo-hydrocarbon; through post-treatment at room temperature for synthesizing the iodo-copper complex, by the following steps: reacting the alcohol with the iodide at room temperature and carrying out post-treatment to obtain the monovalent copper complex . The preparation method comprises the following steps: catalyzing alcohol and iodide to react with the iodide, to synthesize the iodo- hydrocarbyl complex; and the method comprises the following steps: catalyzing alcohol and iodide to react. (by machine translation)

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 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.