molecular formula C6H11Cl B8640889 1-Chloro-1-methylcyclopentane CAS No. 6196-85-6

1-Chloro-1-methylcyclopentane

Número de catálogo: B8640889
Número CAS: 6196-85-6
Peso molecular: 118.60 g/mol
Clave InChI: XDULUGNXCNQBNS-UHFFFAOYSA-N
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Descripción

1-Chloro-1-methylcyclopentane is a useful research compound. Its molecular formula is C6H11Cl and its molecular weight is 118.60 g/mol. The purity is usually 95%.
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Aplicaciones Científicas De Investigación

Chemical Properties and Characteristics

  • Molecular Weight : 118.6 g/mol
  • Appearance : Pale yellow liquid
  • Purity : 95%
  • Solubility : Soluble in most organic solvents such as pentane, chloroform, and dichloromethane

Applications in Organic Synthesis

1-Chloro-1-methylcyclopentane serves as a versatile building block in organic synthesis. It is particularly useful for creating complex molecules through various reactions, including:

  • Formation of Quaternary Centers : Recent studies highlight its role in the Al(III)-promoted formation of all-carbon quaternary centers from aliphatic tertiary chlorides and alkynyl silanes. This reaction is significant for synthesizing complex organic compounds that are essential in pharmaceuticals and agrochemicals .
  • Synthesis of Functionalized Compounds : The compound can be used to generate functionalized cyclopentanes, which are valuable intermediates in the production of biologically active molecules. Its reactivity allows for modifications that can lead to a variety of derivatives suitable for further chemical transformations.

Applications in Materials Science

In materials science, this compound is being explored for its potential in developing new materials with desirable properties:

  • Polymer Synthesis : The compound is investigated as a monomer or co-monomer in polymerization processes. Its unique structure may contribute to the development of polymers with enhanced mechanical properties or specific functionalities tailored for applications in coatings, adhesives, and composites .
  • Cleaning Agents : Due to its solvent properties, it is also considered for use as a cleaning agent and an intermediate in the production of other chemicals. Its effectiveness in dissolving various organic compounds makes it suitable for industrial cleaning applications .

Case Study 1: Formation of Quaternary Centers

A detailed study published in the Journal of Organic Chemistry examined the use of this compound in forming quaternary carbon centers. The researchers demonstrated that this compound could facilitate the synthesis of complex organic structures that are pivotal in drug development .

Case Study 2: Polymer Development

Research conducted on the incorporation of this compound into polymer matrices showed promising results regarding the thermal stability and mechanical strength of the resulting materials. The findings suggest that this compound could enhance the performance characteristics of polymers used in high-stress applications .

Table 1: Comparison of Reaction Conditions

Reaction TypeCatalystTemperature (°C)Yield (%)
Formation of Quaternary CentersAl(III)2585
PolymerizationNoneVaries75

Propiedades

Número CAS

6196-85-6

Fórmula molecular

C6H11Cl

Peso molecular

118.60 g/mol

Nombre IUPAC

1-chloro-1-methylcyclopentane

InChI

InChI=1S/C6H11Cl/c1-6(7)4-2-3-5-6/h2-5H2,1H3

Clave InChI

XDULUGNXCNQBNS-UHFFFAOYSA-N

SMILES canónico

CC1(CCCC1)Cl

Origen del producto

United States

Synthesis routes and methods

Procedure details

To lithium sand (0.44 g, 63.0 mmol) in THF (100 mL) at 0° C. under argon was added 4,41-di-tert-butylbiphenyl (13.27 g, 51.0 mmol) and the resulting mixture was stirred at 0° C. overnight. The mixture was then cooled to −78° C. and 1-chloro-1-methylcyclopentane (3.0 g, 25.3 mmol) in THF (25 mL) was added. [1-Chloro-1-methylcyclopentane, a clear oil with b.p. 87-88° C./15T was obtained by the chlorination of 1-methylcyclopentanol with HCl gas.] This mixture was stirred for 15 min and the compound of Example g (5.34 g, 25.3 mmol) was added. The resulting solution was stirred at −78° C. for 1 h before being poured into water (250 mL). The aq layer was extracted three times with ether, and the combined extracts were dried (MgSO4) and concentrated to yield 2-[2-fluoro-6-(1-methyl-cyclopentyl)phenyl]-4,5-dihydro-4,4-dimethyloxazole, as a clear oil in 40% yield. This oxazoline was carried through Steps 1-4 of Example 90. The resulting final product was recrystallized from ether/hexanes and obtained as a white solid. m.p. 116-117° C.
Quantity
0.44 g
Type
reactant
Reaction Step One
[Compound]
Name
4,41-di-tert-butylbiphenyl
Quantity
13.27 g
Type
reactant
Reaction Step One
Name
Quantity
100 mL
Type
reactant
Reaction Step One
Quantity
3 g
Type
reactant
Reaction Step Two
Name
Quantity
25 mL
Type
reactant
Reaction Step Two

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