100-59-4

Basic information

• Product Name: PHENYLMAGNESIUM CHLORIDE
• Synonyms: PHENYLMAGNESIUM CHLORIDE, 2.0M SOLUTION IN TETRAHYDROFURAN;Phenylmagnesium Chloride 2.0 M In Tetrahdyrofuran;PHENYLMAGNESIUM CHLORIDE 25 WT% IN THF;Phenylmagnesium chloride, 25 wt% solution in tetrahydrofuran;PHENYLMAGNESIUM CHLORIDE, 1 M in DIBUTYL ETHER;PHENYLMAGNESIUM CHLORIDE, 2 M in TETRAHYDROFURAN;Phenylmagnesiumchloride,2-3MinTHF;PHENYLMAGNESIUMCHLORIDE,25%INTETRAHYDROFURAN
• CAS NO: 100-59-4
• Molecular Formula: C₆H₅ClMg
• Molecular Weight: 136.86
• EINECS: 202-868-8
• Product Categories: Organometallics;Classes of Metal Compounds;Grignard Reagents;Grignard Reagents & Alkyl Metals;Mg (Magnesium) Compounds;Synthetic Organic Chemistry;Typical Metal Compounds;Aryl;Grignard Reagents;Organometallic Reagents;grignard reagent
• Mol File: 100-59-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 89-90℃
• Boiling Point: 230℃ (8 Torr)
• Flash Point: 1 °F
• Appearance: yellowish-brown to dark brown solution
• Density: 0.98 g/mL at 20 °C
• Vapor Pressure: 101mmHg at 25°C
• Storage Temp.: water-free area
• Water Solubility: It reacts violently with water.
• Sensitive: Air & Moisture Sensitive
• Merck: 14,7298
• BRN: 3587900
• CAS DataBase Reference: PHENYLMAGNESIUM CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYLMAGNESIUM CHLORIDE(100-59-4)
• EPA Substance Registry System: PHENYLMAGNESIUM CHLORIDE(100-59-4)

Safety Data

• Hazard Codes: F,C
• Statements: 14-19-20/21/22-34-67-65-63-48/20-11-40-37
• Safety Statements: 26-36/37/39-45-62-33-16
• RIDADR: UN 2924 3/PG 2
• WGK Germany: 2
• F: 10
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 100-59-4(Hazardous Substances Data)

Usage

Description

Phenylmagnetic chloride (PhMgCl) is a versatile organometallic compound, primarily used as a Grignard reagent in organic synthesis. It is a yellowish-brown to dark brown solution and has been enhanced for energy efficiency.

Uses

Used in Organic Synthesis:
Phenylmagnetic chloride is used as a Grignard reagent for the production of hydrocarbons, alcohols, ketones, organic acids, amines, silicones, and boranes. It plays a crucial role in various cross-coupling reactions, facilitating the formation of carbon-carbon bonds and enabling the synthesis of complex organic molecules.
Used in Pharmaceutical Synthesis:
Phenylmagnetic chloride is used as a reagent in the synthesis of specific pharmaceutical compounds, such as (?)-phenserine and stephacidin B. Its ability to form carbon-carbon bonds makes it a valuable tool in the development of novel drugs and therapeutic agents.
Used in Energy Storage:
Phenylmagnetic chloride can be used as an electrolyte solution, in combination with aluminium chloride (AlCl3), in the development of rechargeable magnesium batteries. This application highlights its potential in the energy storage industry, contributing to the advancement of more efficient and sustainable battery technologies.
Used in Green Chemistry:
Phenylmagnetic chloride is also employed as a Grignard reagent in greener solvents, such as 2-methyltetrahydrofuran (2-MeTHF). This application demonstrates its utility in promoting environmentally friendly and sustainable chemical processes, reducing the environmental impact of organic synthesis.

InChI:InChI=1/C6H5.ClH.Mg/c1-2-4-6-5-3-1;;/h1-5H;1H;/q-1;;+2/p-1

Upstream product

• 108-90-7 chlorobenzene 
• 591-50-4 iodobenzene 
• 7439-95-4 magnesium 

Downstream Products

• 4544-27-8 (3-methylpenta-1,2-dien-1-yl)benzene 
• 574-66-3 Benzophenone oxime 
• 91111-01-2 (R)-1-oxo-1-phenylpropan-2-yl acetate 
• 1579-80-2 (3,3,3-trifluoropropyl)benzene 
• 152361-78-9 diisopropylphenyl-2-propenylsilane 
• 10519-89-8 diallyldiisopropylsilane 
• 6145-09-1 (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)benzene 
• 1027201-30-4 C-(4-Benzyloxy-3-methoxy-phenyl)-C-phenyl-methyleneamine 
• 157690-42-1 (E)-diethyl (2-phenylpent-1-en-1-yl)phosphonate 
• 185621-29-8 Benzyl 5-(hydroxymethylphenyl)pyrrole-2-carboxylate 
• 185621-38-9 Benzyl 3-hexyl-5-(hydroxymethylphenyl)-4-methylpyrrole-2-carboxylate 
• 5682-83-7 (E)-2-benzylidenecyclohexanone 

Relevant articles and documents

Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides

Magnesium organometallic reagents occupy a central position in organic synthesis. The freshness of these compounds is the key for achieving a high conversion and reproducible results. Common methods for the synthesis of Grignard reagents from metallic magnesium present safety issues and exhibit a batch-to-batch variability. Tubular reactors of solid reagents combined with solution-phase reagents enable the continuous-flow preparation of organomagnesium reagents. The use of stratified packed-bed columns of magnesium metal and lithium chloride for the synthesis of highly concentrated turbo Grignards is reported. A low-cost pod-style synthesizer prototype, which incorporates single-use prepacked perfluorinated cartridges and bags of reagents for the automated on-demand lab-scale synthesis of carbon, nitrogen, and oxygen turbo magnesium bases is presented. This concept will provide access to fresh organomagnesium reagents on a discovery scale and will do so independent from the operator’s experience in flow and/or organometallic chemistry.

Movel photoacid generators, resist compositons, and patterning processes

Photoacid generators generate sulfonic acids of formula (1a) or (1c) upon exposure to high-energy radiation. ????????R1-COOCH(CF3)CF2SO3-H+?????(1a) ????????R1-O-COOCH(CF3)CF2SO3-H+?????(1c) R1 is a C20-C50 hydrocarbon group having a steroid structure. The photoacid generators are compatible with resins and can control acid diffusion and are thus suited for use in chemically amplified resist compositions.

Novel fluorohydroxyalkyl sulfonate salts and derivatives, photoacid generators, resist compositions, and patterning process

Sulfonate salts have the formula: CF3-CH(OH)-CF2SO3-M+ wherein M+ is a Li, Na, K, ammonium or tetramethylammonium ion. Because of inclusion within the molecule of a hydroxyl group which is a polar group, the sulfonic acids are effective for restraining the length of acid diffusion through hydrogen bond or the like. The photoacid generators that generate these sulfonic acids perform well during the device fabrication process including coating, pre-baking, exposure, post-exposure baking, and developing steps. The photoacid generators are little affected by water left on the wafer during the ArF immersion lithography.