10604-60-1

Basic information

• Product Name: 1-iodo-1-phenylethane
• Synonyms: 1-iodo-1-phenylethane;(α-Iodoethyl)benzene;1-Iodoethylbenzene;α-Methylbenzyl iodide
• CAS NO: 10604-60-1
• Molecular Formula: C₈H₉I
• Molecular Weight: 232.06153
• EINECS: 234-228-9
• Mol File: 10604-60-1.mol
• Article Data: 45

Chemical Properties

• Melting Point: 65-66 °C
• Boiling Point: 220.6°Cat760mmHg
• Flash Point: 91.3°C
• Appearance: /
• Density: 1.636g/cm³
• Vapor Pressure: 0.166mmHg at 25°C
• Refractive Index: 1.603
• CAS DataBase Reference: 1-iodo-1-phenylethane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-iodo-1-phenylethane(10604-60-1)
• EPA Substance Registry System: 1-iodo-1-phenylethane(10604-60-1)

Safety Data

• Hazardous Substances Data: 10604-60-1(Hazardous Substances Data)

Usage

General Description

1-Iodo-1-phenylethane, also known as benzyl iodide, is a chemical compound with the formula C8H9I. It is a colorless liquid with a strong and unpleasant odor. It is used as a reagent in organic synthesis, particularly in the formation of carbon-carbon bonds. It is also used as a precursor for the synthesis of other important chemicals, including pharmaceuticals and agrochemicals. Benzyl iodide is considered to be hazardous, as it is toxic if inhaled, swallowed, or in contact with skin, and can cause irritation to the respiratory system and skin. It is flammable and may release dangerous gases when in contact with water or acids.

InChI:InChI=1/C8H9I/c1-7(9)8-5-3-2-4-6-8/h2-7H,1H3

Upstream product

• 96-09-3 styrene oxide 
• 98-85-1 1-Phenylethanol 
• 92976-56-2 tert-butyldimethyl(1-phenylethoxy)silane 
• 105966-39-0 2-(1-phenylethoxy)-tetrahydro-2H-pyran 
• 100-41-4 ethylbenzene 
• 672-65-1 (1-chloroethyl)benzene 
• 14856-75-8 1-phenyl-1-trimethylsilyloxyethane 
• 100-42-5 styrene 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 98-86-2 acetophenone 
• 104745-42-8 1-phenylethyldimethylphenylammonium iodide 
• 677-22-5 tert-butylmagnesium chloride 
• 74-88-4 methyl iodide 
• 94073-86-6 (1-methoxymethoxy)ethylbenzene 

Downstream Products

• 672-65-1 (1-chloroethyl)benzene 
• 100-42-5 styrene 
• 4613-11-0 2,3-diphenylbutane 
• 2726-21-8 2,3-diphenylbutane 
• 32366-25-9 1-azidoethylbenzene 
• 4809-56-7 N-(1-phenylethyl)-p-toluenesulfonamide 
• 98-86-2 acetophenone 
• 10340-49-5 4-phenyl-1-pentene 
• 492-37-5 hydratropic acid 
• 1100569-50-3 C₁₄H₁₅NO₂ 
• 70096-24-1 (η5-C5H5)Fe(CO)(CN)(α-phenylethyl isocyanide) 
• 60263-93-6 S-(1-phenylethyl)-2-thiopyridine N-oxide 

Relevant articles and documents

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Iodination of alcohols using triphenylphosphine/iodine under solvent-free conditions using microwave irradiation

A straightforward and effective procedure for the conversion of benzylic, allylic and aliphatic alcohols to the corresponding iodides using Ph3P/I2 under solvent-free conditions using microwave irradiation is reported.

Silica chloride in the presence of NaI is a useful system for the efficient and selective conversion of TMS, TBDMS and THP ethers into their corresponding iodides

Direct and highly selective conversion of benzylic, allylic and propargylic TMS, TBDMS and THP ethers into their corresponding iodides with the SiO2-Cl/NaI system is described. Reactions were conducted in CH3CN at room temperature. Aliphatic silyl and tetrahydropyranyl ethers remained almost intact under similar reaction conditions.

An expedient stereoselective synthesis of (Z)- and (E)-allyl iodides from Baylis-Hillman adducts along with selective iodination of benzylic alcohols using the polymethylhydrosiloxane-iodine system

A stereoselective method has been developed for the synthesis of (Z)- and (E)-allyl iodides from Baylis-Hillman adducts using polymethylhydrosiloxane (PMHS) and iodine in chloroform at room temperature. In addition, the reagent system has been utilized for the iodination of benzylic alcohols selectively.

Iodination of alcohols using triphenylphosphine/iodine in ionic liquid under solvent-free conditions

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An efficient and facile hydroiodination of alkenes and alkynes PI using polymethylhydrosiloxane-iodine system

A mild and efficient method has been developed for the synthesis of alkyl and alkenyl iodides from alkenes and alkynes using polymethylhydrosiloxane (PMHS) and iodine in chloroform at room temperature. The reagent system generates hydrogen iodide which regioselectively adds to the alkenes and alkynes. Copyright

Convenient and efficient method for the iodination of benzylic and aliphatic alcohols by using Al(HSO4)3/KI in nonaqueous solution

A simple and efficient method for the iodination of benzylic and aliphatic alcohols by using Al(HSO4)3/KI in n-hexane as solvent is reported. Mild reaction conditions and good to excellent yields of the products are the noteworthy advantages of the method. Copyright Taylor & Francis LLC.

An expedient and highly selective iodination of alcohols using a KI/BF3·Et2O system

Alkyl iodides are prepared in high yields by treatment of allylic and benzylic alcohols with an equimolar amount of KI in the presence of BF3·Et2O in dioxane under mild conditions.

Allyl and benzyl iodides by the anomalous action of iodotrimethylsilane

Iodotrimethylsilane (TMSI), routinely used for the dealkylation of ethers and esters, has been found to efficiently convert allyl and benzyl phosphotriesters into the corresponding iodides under mild, Bronsted-neutral conditions. In contrast, alkyl and aryl phosphotriesters were dealkylated to the corresponding phosphates under identical conditions.

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.

Ready access to organoiodides: Practical hydroiodination and double-iodination of carbon-carbon unsaturated bonds with I2

By using I2 or I2/H3PO3 system, various alkenes and alkynes were converted to the corresponding alkyl and alkenyl iodides in good yields. In the presence of I2, alkynes could be di-iodinated using H2O as the solvent in air at room temperature. This method also features the simple work-up procedure since the pure product could be obtained by extraction. Additionally, for the first time, combining with the non-toxic and cheap phosphonic acid H3PO3, alkenes and alkynes were also hydroiodinated successfully, which provides a simple and practical approach for synthesis of organoiodides.

Silica gel-mediated hydrohalogenation of unactivated alkenes using hydrohalogenic acids under organic solvent-free conditions

Silica gel-mediated hydrochlorination of unactivated alkenes using 35% hydrochloric acid under organic solvent-free conditions proceeded to give the corresponding chlorides in good yields. Hydrobromination or hydriodination using 47% hydrobromic acid or 55% hydriodic acid afforded the corresponding halides, respectively. Silica gel could be recycled five times without any significant loss of activities.