931-51-1

Basic information

• Product Name: Magnesium,chlorocyclohexyl-
• Synonyms: Chlorocyclohexylmagnesium;Cyclohexylmagnesium chloride;chloro-cyclohexyl-magnesium;Cyclohexylmagnesium chloride solution
• CAS NO: 931-51-1
• Molecular Formula: C₆H₁₁ClMg
• Molecular Weight: 142.9095
• EINECS: 213-237-1
• Product Categories: Alkyl;Grignard Reagents;Organometallic Reagents
• Mol File: 931-51-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 80.7ºC at 760 mmHg
• Flash Point: -40 °F
• Appearance: clear very dark brown solution
• Density: 0.871 g/mL at 25ºC
• Storage Temp.: Flammables + water-Freezer (-20°C)e area
• Water Solubility: It reacts violently with water.
• BRN: 3535440
• CAS DataBase Reference: Magnesium,chlorocyclohexyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Magnesium,chlorocyclohexyl-(931-51-1)
• EPA Substance Registry System: Magnesium,chlorocyclohexyl-(931-51-1)

Safety Data

• Hazard Codes: F+,C,F
• Statements: 12-14/15-19-22-34-67-66-14-65-48/20-40-37-11-63
• Safety Statements: 7-9-16-26-29-33-36/37/39-43-45-62
• RIDADR: UN 3399 4.3/PG 1
• WGK Germany: 1
• F: 1-3-10
• TSCA: Yes
• HazardClass: 4.2
• PackingGroup: I
• Hazardous Substances Data: 931-51-1(Hazardous Substances Data)

Usage

Chemical Properties

clear very dark brown solution

Uses

Different sources of media describe the Uses of 931-51-1 differently. You can refer to the following data:
1. Cyclohexylmagnesium chloride is used as a Grignard reagent in greener solvent, 2-methyltetrahydrofuran (2-MeTHF). It is used as a reagent for the introduction of the cyclohexyl group; metalation of CH-acidic compounds.
2. Nucleophilic reagent is commonly used in substitution and addition reactions.

InChI:InChI=1/C6H11.ClH.Mg/c1-2-4-6-5-3-1;;/h1H,2-6H2;1H;/q;;+1/p-1/rC6H11Mg.ClH/c7-6-4-2-1-3-5-6;/h6H,1-5H2;1H/q+1;/p-1

Upstream product

• 542-18-7 cyclohexyl chloride 
• 7439-95-4 magnesium 

Downstream Products

• 854696-45-0 cyclohexyl(tetrahydro-2H-pyran-4-yl)methanone 
• 858423-14-0 1-cyclohexyl-2-methyl-cyclopentene 
• 25246-83-7 cyclohexyl tert-butyl ether 
• 92-51-3 cyclohexylcyclohexane 
• 119-60-8 dicyclohexyl ketone 
• 17687-74-0 α,α-dicyclohexyl-cyclohexanemethanol 
• 945-49-3 cyclohexylphenylmethanol 
• 87839-87-0 α,α-Dicyclohexylbenzolmethanol 
• 50284-86-1 1-chloro-2-cyclohexylethyne 
• 109259-44-1 bis(isobutyloxy)cyclohexylborane 
• 82215-84-7 1-cyclohexyl-2-dimethylamino-propan-1-one 
• 4453-82-1 Dicyclohexylmethanol 
• 58435-70-4 cyclohexyl methoxymethyl ketone 
• 872267-21-5 cyclohexyl(cyclopentyl)methanol 

Relevant articles and documents

Iron-Catalyzed Cross-Coupling of Alkynyl and Styrenyl Chlorides with Alkyl Grignard Reagents in Batch and Flow

Transition-metal-catalyzed cross-coupling chemistry can be regarded as one of the most powerful protocols to construct carbon–carbon bonds. While the field is still dominated by palladium catalysis, there is an increasing interest to develop protocols that utilize cheaper and more sustainable metal sources. Herein, we report a selective, practical, and fast iron-based cross-coupling reaction that enables the formation of Csp?Csp3 and Csp2?Csp3 bonds. In a telescoped flow process, the reaction can be combined with the Grignard reagent synthesis. Moreover, flow allows the use of a supporting ligand to be avoided without eroding the reaction selectivity.

DIALKYL(2-ALKOXY-6-AMINOPHENYL)PHOSPHINE, THE PREPARATION METHOD AND USE THEREOF

The present invention relates to the compound of dialkyl(2-alkoxy-6-aminophenyl)phosphine and the preparation method thereof and the application in the palladium catalyzed coupling reactions of aryl chloride and ketone. The dialkyl(2-alkoxy-6-aminophenyl)phosphine of the present invention could coordinate with the palladium catalyst to highly selectively activate the inert carbon-chlorine bond, and to catalyze direct arylation reaction in the α-position of ketones to produce corresponding coupling compounds. The preparation method of the present invention is a simple one-step method which produces the air-stable dialkyl(2-alkoxy-6-aminophenyl)phosphine. Compared with the synthetic routes of ligands to be used in the activation of carbon-chlorine bonds in the prior arts, the preparation method of the present invention has the advantages of short route and easy operation.

STRUCTURE AND METHOD FOR SYNTHESIZING AND USING DIALKYL(2,4,6- OR 2,6-ALKOXYPHENYL)PHOSPHINE AND ITS TETRAFLUOROBORATE

The current invention relates to the structure, synthesis of dialkyl(2,4,6- or 2,6-alkoxyphenyl)phosphine or its tetrafluoroborate, as well as its applications in the palladium catalyzed carbon-chlorine bond activation for Suzuki coupling reactions and carbon-nitrogen bond formation reactions. The dialkyl(2,4,6- or 2,6-alkoxyphenyl)phosphine or its tetrafluoroborate could coordinate with the palladium catalyst to activate the inert carbon-chlorine bond highly selectively and catalyze Suzuki coupling reaction with arylboronic acid or carbon-nitrogen bond formation reaction with organic amines. The current invention uses only one step to synthesize dialkyl(2,4,6- or 2,6-alkoxyphenyl)phosphine and its tetrafluoroborate is stable in the air. Compared with known synthetic routes of ligands used in activating carbon-chlorine bonds, the method of current invention is short, easy to operate. Moreover, with this type of ligands, the Suzuki coupling products of optically active chlorolactones and arylboronic acids would maintain their configuration and optical purity.