28987-79-3

Basic information

• Product Name: M-TOLYLMAGNESIUM BROMIDE
• Synonyms: M-TOLYLMAGNESIUM BROMIDE;3-METHYLPHENYLMAGNESIUM BROMIDE;Tolylmagnesiumbromide;M-TOLYLMAGNESIUM BROMIDE: 19% IN TETRAHYDROFURAN, 1M);m-Tolylmagnesium Bromide (19% in Tetrahydrofuran, ca. 1mol/L);3-Tolylmagnesium bromide;m-Methylphenylmagnesium bromide;m-Methyphenylmagnesium bromide
• CAS NO: 28987-79-3
• Molecular Formula: C₇H₇BrMg
• Molecular Weight: 195.34
• Product Categories: Classes of Metal Compounds;Grignard Reagents;Grignard Reagents & Alkyl Metals;Mg (Magnesium) Compounds;Synthetic Organic Chemistry;Typical Metal Compounds;Grignard Reagent
• Mol File: 28987-79-3.mol
• Article Data: 9

Chemical Properties

• Flash Point: -17°C (THF)
• Appearance: /
• CAS DataBase Reference: M-TOLYLMAGNESIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: M-TOLYLMAGNESIUM BROMIDE(28987-79-3)
• EPA Substance Registry System: M-TOLYLMAGNESIUM BROMIDE(28987-79-3)

Safety Data

• Statements: 11-14/15-19-34
• Safety Statements: 16-26-43-24/25
• RIDADR: 2924
• HazardClass: 3/8
• PackingGroup: II
• Hazardous Substances Data: 28987-79-3(Hazardous Substances Data)

Usage

General Description

M-Tolylmagnesium bromide is a chemical compound commonly used as a reagent in organic synthesis. It is a Grignard reagent, which means it is a key component in the formation of new carbon-carbon bonds in organic molecules. M-TOLYLMAGNESIUM BROMIDE is derived from toluene, a common aromatic hydrocarbon, and magnesium metal, through a reaction with bromine. M-Tolylmagnesium bromide is often used in the synthesis of various pharmaceuticals and fine chemicals. It is a highly reactive and potent nucleophile, making it valuable for the creation of complex organic molecules in a laboratory setting.

InChI:InChI=1/C7H7.BrH.Mg/c1-7-5-3-2-4-6-7;;/h2-3,5-6H,1H3;1H;/q;;+1/p-1/rC7H7BrMg/c1-6-3-2-4-7(5-6)9-8/h2-5H,1H3

Upstream product

• 591-17-3 meta-bromotoluene 
• 7439-95-4 magnesium 

Downstream Products

• 1875-89-4 2-(3-methylphenyl)ethanol 
• 112820-02-7 acetic acid-[2-(α-hydroxy-3,3'-dimethyl-benzhydryl)-anilide] 
• 114001-69-3 2-(4-ethoxy-phenyl)-3-m-tolyl-inden-1-one 
• 6957-08-0 1-(m-Methylphenyl)cyclohexanol 
• 585-74-0 3-Methylacetophenone 
• 860376-18-7 1-chloro-2-(3-methylbenzyl)benzene 
• 149243-82-3 (2-chlorophenyl)(m-tolyl)methanol 
• 53039-63-7 (4-methoxyphenyl)(3-methylphenyl)methanone 
• 21855-82-3 4-(3-methylphenyl)-1,2-dihydronaphthalene 
• 52056-23-2 2-hydroxy-1,2-diphenyl-2-m-tolyl-ethanone 
• 3333-20-8 1-allyl-3-methylbenzene 
• 96857-15-7 1-(1-ethyl-propyl)-3-methyl-benzene 
• 24826-67-3 (+/-)-2-hydroxy-1-m-tolyl-propane 
• 20808-44-0 1-chloro-3-m-tolyl-propan-2-ol 

Relevant articles and documents

Room-Temperature Palladium(II)-Catalyzed Direct 2-Arylation of Indoles with Tetraarylstannanes

A palladium(II)-catalyzed direct 2-arylation of indoles by tetraarylstannanes with oxygen (balloon) as the oxidant at room temperature has been developed. Various tetraarylstannanes can be employed as aryl sources for 2-arylation of indoles in up to 89% yield, providing a practical and efficient catalytic protocol for accessing 2-arylindoles.

Nickel-Catalyzed Asymmetric Kumada Cross-Coupling of Symmetric Cyclic Sulfates

Nickel-catalyzed enantioselective cross-couplings between symmetric cyclic sulfates and aromatic Grignard reagents are described. These reactions are effective with a broad range of substituted cyclic sulfates and deliver products with asymmetric tertiary carbon centers. Mechanistic experiments point to a stereoinvertive SN2-like oxidative addition of a nickel complex to the electrophilic substrate.

Bismuth-catalyzed synthesis of polycyclic aromatic hydrocarbons (PAHs) with a phenanthrene backbone via cyclization and aromatization of 2-(2-arylphenyl)vinyl ethers

The reaction of 2-(2-arylphenyl)vinyl ethers in the presence of a catalytic amount of bismuth(III) triflate gave substituted phenanthrenes in excellent yields under mild reaction conditions. The reaction was also applied to the construction of other polycyclic aromatic hydrocarbons (PAHs), such as chrysene, helicene, and pyrene having a phenanthrene backbone, via regioselective cyclization. This method has the advantages of easy availability of the cyclization precursors, operational simplicity, and high reaction efficiency.