Cyclohexylmagnesium chloride

Base Information

• Chemical Name: Cyclohexylmagnesium chloride
• CAS No.: 931-51-1
• Molecular Formula: C6H11ClMg
• Molecular Weight: 142.911
• Hs Code.: 29319090
• European Community (EC) Number: 213-237-1
• DSSTox Substance ID: DTXSID2061309
• Mol file: 931-51-1.mol

Synonyms:CYCLOHEXYLMAGNESIUM CHLORIDE;931-51-1;Magnesium, chlorocyclohexyl-;cyclohexylmagnesiumchloride;magnesium;cyclohexane;chloride;Chlorocyclohexylmagnesium;UNII-OAG686RDSU;Magnesium,chlorocyclohexyl-;HSDB 5772;EINECS 213-237-1;MFCD00003816;EC 213-237-1;cyclohexyl magnesium chloride;C6H11ClMg;Cyclohexylmagnesium cloride;OAG686RDSU;C6-H11-Cl-Mg;cyclohexyl-magnesium chloride;SCHEMBL351952;DTXSID2061309;CHLORO(CYCLOHEXYL)MAGNESIUM;WMJMABVHDMRMJA-UHFFFAOYSA-M;AKOS000121179;Cyclohexylmagnesium chloride, 1M in MeTHF;Cyclohexylmagnesium chloride, 1.0 M in 2-MeTHF;Cyclohexylmagnesium chloride 0.5 M in Tetrahydrofuran;Cyclohexylmagnesium chloride 1.0 M in Tetrahydrofuran;F0001-2245

Chemical Property of Cyclohexylmagnesium chloride

Chemical Property:

• Appearance/Colour: clear very dark brown solution
• Boiling Point: 80.7ºC at 760 mmHg
• Flash Point: -40 °F
• PSA: 0.00000
• Density: 0.871 g/mL at 25ºC
• LogP: 2.97780
• Storage Temp.: Flammables + water-Freezer (-20°C)e area
• Water Solubility.: It reacts violently with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 142.0399697
• Heavy Atom Count: 8
• Complexity: 35.5

Purity/Quality:

99% ^*data from raw suppliers

Cyclohexylmagnesium chloride solution ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F+;C
• 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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Metals -> Metals, Organic Compounds
• Canonical SMILES: C1CC[CH-]CC1.[Mg+2].[Cl-]
• Uses: 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. Nucleophilic reagent is commonly used in substitution and addition reactions.

Technology Process of Cyclohexylmagnesium chloride

There total 3 articles about Cyclohexylmagnesium chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

cyclohexyl chloride (542-18-7) → cyclohexylmagnesiumchloride (931-51-1)

Guidance literature:

With magnesium; In diethyl ether; for 2.5h; Heating;

DOI:10.1039/b210114a

Reference yield:

cyclohexyl chloride (542-18-7) + magnesium (7439-95-4) → cyclohexylmagnesiumchloride (931-51-1)

Guidance literature:

In tetrahydrofuran;

Reference yield:

→ cyclohexylmagnesiumchloride (931-51-1)

Guidance literature:

upstream raw materials:

cyclohexyl chloride

magnesium

Downstream raw materials:

cyclohexylethan-1-ol

2-cyclohexyl-2-hydroxy-propionic acid ethyl ester

cyclohexyl(tetrahydro-2H-pyran-4-yl)methanone

1-cyclohexyl-2-methyl-cyclopentene

Refernces

Kulinkovich-type reactions of thioamides: Similar to those of carboxylic amides?

10.1039/c2cc31394d

The study investigates the behavior of thioamides under Kulinkovich-type conditions and compares it with that of carboxylic amides. The main chemicals involved are thioamides (such as 1aS, 1bS, 1cS, etc.) and carboxylic amides (such as 1aO, 1bO, 1cO, etc.), which serve as the starting materials for the reactions. Alkoxytitanium(IV) species like Ti(OiPr)4 are used as reagents to mediate the transformations. Grignard reagents, including cyclopentylmagnesium chloride and cyclohexylmagnesium chloride, play a crucial role in the reactions. The study finds that thioamides exhibit dramatically different behaviors from carboxylic amides under these conditions. For instance, while carboxylic amides typically undergo intramolecular Kulinkovich–de Meijere reactions to form cyclopropylamines, thioamides can also undergo reductive alkylation processes to form tertiary amines, with the initially formed titanacyclopropane reacting faster with thioamide functions than with alkene groups. The researchers propose a mechanism involving the formation of a thia-titanacyclopropane intermediate, which can be trapped intramolecularly by an olefin group or lead to the production of secondary amines through a competitive pathway.

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