23665-09-0

Basic information

• Product Name: PHENYLZINC IODIDE
• Synonyms: PHENYLZINC IODIDE;PHENYLZINC IODIDE, 0.5M SOLUTION IN TETR A-HYDROFURAN;phenylzinc iodide solution;Iodophenylzinc;Phenylzinc iodide solution 0.5 in THF;phenylzinc(II) iodide;Phenylzinc iodide, 0.5 M solution in THF, SpcSeal;Phenylzinc iodide, 0.50 M in THF
• CAS NO: 23665-09-0
• Molecular Formula: C₆H₅IZn
• Molecular Weight: 269.4
• Product Categories: Aryl;Organozinc Halides;Reike and Organozinc Reagents
• Mol File: 23665-09-0.mol
• Article Data: 15

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: 1 °F
• Appearance: /
• Density: 0.966 g/mL at 25 °C
• Storage Temp.: 2-8°C
• Water Solubility: Reacts with water.
• Sensitive: Air Sensitive
• CAS DataBase Reference: PHENYLZINC IODIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYLZINC IODIDE(23665-09-0)
• EPA Substance Registry System: PHENYLZINC IODIDE(23665-09-0)

Safety Data

• Hazard Codes: F,C,Xn
• Statements: 11-14/15-19-34-40-36/37
• Safety Statements: 16-26-36/37/39-45-36/37
• RIDADR: UN 3399 4.3/PG 2
• WGK Germany: 1
• HazardClass: 4.3
• Hazardous Substances Data: 23665-09-0(Hazardous Substances Data)

Usage

General Description

Phenylzinc iodide, also known as phenylmagnesium bromide, is an organometallic compound that is widely used as a synthetic reagent in organic chemistry. It is commonly used in organic synthesis as a source of the phenyl anion. PHENYLZINC IODIDE is typically utilized in the Grignard reaction, where it can add to a variety of electrophiles, such as carbonyl compounds, to form new carbon-carbon bonds. Phenylzinc iodide is also used in the preparation of aryl ketones, as well as in the synthesis of pharmaceuticals and natural products. It is important to handle this compound with caution, as it is highly reactive and can undergo rapid decomposition in the presence of air or moisture. Overall, phenylzinc iodide is a versatile chemical that plays a key role in the development of various organic compounds.

InChI:InChI=1/C6H5.HI.Zn/c1-2-4-6-5-3-1;;/h1-5H;1H;/q;;+1/p-1/rC6H5IZn/c7-8-6-4-2-1-3-5-6/h1-5H

Upstream product

• 16002-63-4 phenylmagnesium iodide 
• 10139-47-6 zinc(II) iodide 
• 100-58-3 phenylmagnesium bromide 
• 7440-66-6 zinc 
• 591-50-4 iodobenzene 

Downstream Products

• 119-61-9 benzophenone 
• 2689-59-0 (furan-2-yl)(phenyl)methanone 
• 6136-67-0 3-methoxybenzophenone 
• 644-13-3 C₆H₅COC₁₀H₇ 
• 71-43-2 benzene 
• 1048958-14-0 1-phenyl-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 
• 1582284-70-5 1-methyl-1-phenyl-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 
• 1582284-71-6 1-ethyl-1-phenyl-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 
• 1582284-72-7 1-isopropyl-1-phenyl-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 
• 1582284-73-8 1-(4-tolyl)-1-phenyl-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Enantioselective Conjugate Addition of Stabilized Arylzinc Iodide to Enones: an Improved Protocol of the Hayashi Reaction

Stabilised arylzinc iodide, prepared by direct insertion of zinc into aryl iodides, were used as nucleophiles in the Hayashi Rh-catalysed enantioselective conjugate addition to enones. The reaction conditions were optimized in the addition of phenylzinc i

Nickel-Catalyzed α-Carbonylalkylarylation of Vinylarenes: Expedient Access to γ,γ-Diarylcarbonyl and Aryltetralone Derivatives

We report a Ni-catalyzed regioselective α-carbonylalkylarylation of vinylarenes with α-halocarbonyl compounds and arylzinc reagents. The reaction works with primary, secondary, and tertiary α-halocarbonyl molecules, and electronically varied arylzinc reagents. The reaction generates γ,γ-diarylcarbonyl derivatives with α-secondary, tertiary, and quaternary carbon centers. The products can be readily converted to aryltetralones, including a precursor to Zoloft, an antidepressant drug.

Ni-Catalyzed Regioselective β,δ-Diarylation of Unactivated Olefins in Ketimines via Ligand-Enabled Contraction of Transient Nickellacycles: Rapid Access to Remotely Diarylated Ketones

We disclose a [(PhO)3P]/NiBr2-catalyzed regioselective β, δ-diarylation of unactivated olefins in ketimines with aryl halides and arylzinc reagents. This diarylation proceeds at remote locations to the carbonyl group to afford, after simple H+ workup, diversely substituted β, δ-diarylketones that are otherwise difficult to access readily with existing methods. Deuterium-labeling and crossover experiments indicate that diarylation proceeds by ligand-enabled contraction of transient nickellacycles.