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Phenylmagnesium iodide, with the chemical formula C6H5MgI, is a Grignard reagent, an organometallic compound known for its high reactivity and versatility in organic synthesis. It is synthesized by reacting bromobenzene with magnesium in the presence of an iodine catalyst. PHENYLMAGNESIUM IODIDE serves as a potent nucleophile, facilitating the formation of carbon-carbon bonds, including aryl-aryl, aryl-alkyl, and aryl-heteroatom bonds. Its applications extend to the synthesis of pharmaceuticals, natural products, and a variety of other organic compounds. Due to its reactivity, phenylmagnesium iodide must be carefully handled and stored under anhydrous and inert conditions to prevent unwanted reactions.

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  • 16002-63-4 Structure
  • Basic information

    1. Product Name: PHENYLMAGNESIUM IODIDE
    2. Synonyms: PHENYLMAGNESIUM IODIDE;42%inethyletherca.2mol/L;Phenylmagnesium Iodide (42% in Ethyl Ether, ca. 2mol/L);Phenyliodomagnesium;PhenylMagnesiuM Iodide PhenylMagnesiuM Iodide (ca. 42% in Ethyl Ether, ca. 2Mol/L);Phenylmagnesium iodide, 0.50 M in THF
    3. CAS NO:16002-63-4
    4. Molecular Formula: C6H5IMg
    5. Molecular Weight: 228.31
    6. EINECS: N/A
    7. Product Categories: Classes of Metal Compounds;Grignard Reagents;Grignard Reagents & Alkyl Metals;Mg (Magnesium) Compounds;Synthetic Organic Chemistry;Typical Metal Compounds;Pharm intermediate
    8. Mol File: 16002-63-4.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: PHENYLMAGNESIUM IODIDE(CAS DataBase Reference)
    10. NIST Chemistry Reference: PHENYLMAGNESIUM IODIDE(16002-63-4)
    11. EPA Substance Registry System: PHENYLMAGNESIUM IODIDE(16002-63-4)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. RIDADR: UN 2924 3/8/PG I
    5. WGK Germany:
    6. RTECS:
    7. HazardClass: 3/8
    8. PackingGroup: I
    9. Hazardous Substances Data: 16002-63-4(Hazardous Substances Data)

16002-63-4 Usage

Uses

Used in Organic Synthesis:
Phenylmagnesium iodide is used as a nucleophilic agent for the formation of carbon-carbon bonds, which is crucial in the synthesis of complex organic molecules. Its ability to form aryl-aryl, aryl-alkyl, and aryl-heteroatom bonds makes it a valuable reagent in constructing molecular frameworks.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, phenylmagnesium iodide is utilized as a key intermediate in the synthesis of various drugs. Its reactivity allows for the creation of specific molecular structures that are essential for the development of new medicinal compounds.
Used in Natural Product Synthesis:
Phenylmagnesium iodide is employed as a synthetic building block in the preparation of natural products. Its versatility in forming different types of carbon-carbon bonds is particularly useful in mimicking the complex structures found in natural substances.
Used in Academic Research:
In academic research, phenylmagnesium iodide is used as a tool to explore new reaction pathways and mechanisms in organic chemistry. Its reactivity provides opportunities for studying the fundamental principles of chemical bond formation and the development of novel synthetic methods.

Check Digit Verification of cas no

The CAS Registry Mumber 16002-63-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,0,0 and 2 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 16002-63:
(7*1)+(6*6)+(5*0)+(4*0)+(3*2)+(2*6)+(1*3)=64
64 % 10 = 4
So 16002-63-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H5.HI.Mg/c1-2-4-6-5-3-1;;/h1-5H;1H;/q;;+1/p-1/rC6H5IMg/c7-8-6-4-2-1-3-5-6/h1-5H

16002-63-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name Phenylmagnesium Iodide&nbsp

1.2 Other means of identification

Product number -
Other names phenyl-lithiu

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:16002-63-4 SDS

16002-63-4Relevant articles and documents

An N-Fluorinated Imide for Practical Catalytic Imidations

Adachi, Akiya,Aikawa, Kohsuke,Hashimoto, Takuya,Ishibashi, Yuichiro,Oe, Yuno,Okazoe, Takashi,Tanaka, Airi,Yoshida, Ryuhei

supporting information, (2022/02/10)

Catalytic imidation using NFSI as the nitrogen source has become an emerging tool for oxidative carbon-nitrogen bond formation. However, the less than ideal benzenesulfonimide moiety is incorporated into products, severely detracting its synthetic value.

Efficient C(sp3)-H bond functionalization of isochroman by azadol catalysis

Muramatsu, Wataru,Nakano, Kimihiro

supporting information, p. 1549 - 1552 (2015/03/30)

A novel organocatalytic C(sp3)-H bond functionalization of isochroman under practical conditions has been developed. In the presence of 5.0 mol % of AZADOL, the catalysis proceeded successfully with a broad range of substrates and nucleophiles in excellent yields.

PLATINUM COMPLEXES

-

Page/Page column 32, (2008/06/13)

The invention aims at providing platinum complexes useful as materials for light emitting devices and extremely excellent in heat stability, luminous characteristics, and luminous efficiency, and a process for effective preparation thereof. The invention relates to platinum complexes represented by the general formula [1]: wherein any two of A, B and C are each independently an optionally substituted nitrogenous aromatic heterocyclic group and the other is optionally substituted aryl or optionally substituted heteroaryl; and Y is halogeno or an optionally substituted aryl or heteroaryl group which is bonded either directly or through oxygen (-O-) or sulfur (-S-) (with the proviso that when the adjacent two rings are nitrogenous aromatic heterocyclic groups, the cases wherein Y is chloro are excepted, while when the nonadjacent two rings are nitrogenous aromatic heterocyclic groups, the cases wherein Y is not halogeno are excepted).

Nodulisporic acid derivatives

-

, (2008/06/13)

The present invention relates to novel nodulosporic acid derivatives, which are acaricidal, antiparasitic, insecticidal and anthelmintic agents.

Kinetics and Thermodynamics of Oxidation of Magnesium with Phenyl Halides in Benzene in the Presence of Diethyl Ether

Maslennikov,Spirina

, p. 274 - 276 (2007/10/03)

The equilibrium constants and the enthalpies and entropies of adsorption of phenyl chloride and phenyl iodide on the surface of magnesium during oxidation in benzene were determined. The reaction scheme explaining acceleration of conversion and increase in the fraction of products of the Wuertz reaction with increasing concentration of oxidant was suggested.

OXIDATION OF METALLIC MAGNESIUM WITH ARYL HALIDES IN DIPOLAR APROTIC SOLVENTS

Kondin, A. V.,Smirnova, M. Yu.,Maslennikov, V. P.

, p. 32 - 34 (2007/10/02)

The dependence of the specific rate of oxidation of metallic magesium with aryl halides on the donor number of the ligand used has an extremum character.This demonstrates the selectivity of adsorption of the complexing agent participating in the process o

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