Cyclopentylmagnesium chloride

Base Information

• Chemical Name: Cyclopentylmagnesium chloride
• CAS No.: 32916-51-1
• Molecular Formula: C5H9ClMg
• Molecular Weight: 128.884
• Hs Code.: 29319090
• European Community (EC) Number: 629-215-3
• Mol file: 32916-51-1.mol

Synonyms:cyclopentylmagnesium chloride;32916-51-1;Cyclopentyl magnesium chloride;magnesium;cyclopentane;chloride;cylopentylmagnesium chloride;Cyclopentylmagnesium cloride;SCHEMBL4985;cylopentyl magnesium chloride;GROGEABZCKQTJW-UHFFFAOYSA-M;MFCD00001357;Cyclopentylmagnesium chloride, 1M in MeTHF;Cyclopentylmagnesium chloride, 1.0 M in THF;Cyclopentylmagnesium chloride, 1.0 M in 2-MeTHF

Chemical Property of Cyclopentylmagnesium chloride

Chemical Property:

• Vapor Pressure: 314mmHg at 25°C
• Boiling Point: 49.2°C at 760 mmHg
• Flash Point: -40 °F
• PSA: 0.00000
• Density: 0.86 g/cm³
• LogP: 2.58770
• Sensitive.: Air & Moisture Sensitive
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 128.0243197
• Heavy Atom Count: 7
• Complexity: 27.3

Purity/Quality:

97% ^*data from raw suppliers

Cyclopentylmagnesium chloride solution 2.0M in diethyl ether ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F+,C
• Hazard Codes: F+,C,F
• Statements: 12-14/15-19-22-34-66-67-11
• Safety Statements: 26-36/37/39-43-45-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC[CH-]C1.[Mg+2].[Cl-]

Technology Process of Cyclopentylmagnesium chloride

There total 2 articles about Cyclopentylmagnesium 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:

cyclopentyl chloride (930-28-9) → cyclopentylmagnesium chloride (32916-51-1)

Guidance literature:

With iodine; magnesium; ethylene dibromide; In diethyl ether; for 6h; Reflux; Inert atmosphere;

Reference yield:

cyclopentyl chloride (930-28-9) + magnesium (7439-95-4) → cyclopentylmagnesium chloride (32916-51-1)

Guidance literature:

In tetrahydrofuran;

Reference yield: 90.0%

carbon dioxide (124-38-9,18923-20-1) + cyclopentylmagnesium chloride (32916-51-1) → cyclopentanecarboxylic acid (3400-45-1) + cis β-deuteriated cyclopentanecarboxylic acid

Guidance literature:

cyclopentylmagnesium chloride; With titanium(IV) isopropylate; In diethyl ether; at -78 - -50 ℃; for 0.216667h;

carbon dioxide; In diethyl ether; at -78 - -30 ℃; for 0.5h;

With water-d2; In diethyl ether; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2006.08.117

upstream raw materials:

cyclopentyl chloride

magnesium

Downstream raw materials:

2-cyclopentyl-ethanol

1-amino-cyclopentanemethanol

formaldehyde-(bis-cyclopentylmethyl-acetal)

1-cyclopentyl-2-methoxyethanone

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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