1556-08-7

Basic information

• Product Name: chlorocyclooctane
• Synonyms: chlorocyclooctane
• CAS NO: 1556-08-7
• Molecular Formula: C₈H₁₅Cl
• Molecular Weight: 146.6577
• EINECS: 216-309-0
• Mol File: 1556-08-7.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 200.5°Cat760mmHg
• Flash Point: 64°C
• Appearance: /
• Density: 0.95g/cm³
• Vapor Pressure: 0.459mmHg at 25°C
• Refractive Index: 1.454
• CAS DataBase Reference: chlorocyclooctane(CAS DataBase Reference)
• NIST Chemistry Reference: chlorocyclooctane(1556-08-7)
• EPA Substance Registry System: chlorocyclooctane(1556-08-7)

Safety Data

• Hazardous Substances Data: 1556-08-7(Hazardous Substances Data)

Usage

Description

Chlorocyclooctane, with the chemical formula C8H15Cl, is a colorless liquid chemical compound that features a cyclooctane ring with a chlorine atom attached. It is known for its mild, sweet odor and relative stability under normal conditions, and it is commonly used as a solvent in various industrial and laboratory applications.

Uses

Used in Industrial Applications:
Chlorocyclooctane is utilized as a solvent for its ability to dissolve a wide range of substances, facilitating various chemical processes and reactions in different industries.
Used in Laboratory Applications:
In laboratories, chlorocyclooctane serves as a solvent, enabling researchers to carry out experiments and reactions that require a stable and effective medium.
Used in Pesticide Production:
Chlorocyclooctane is employed as an intermediate in the synthesis of pesticides, contributing to the development of agricultural chemicals that protect crops from pests and diseases.
Used in Organic Compound Synthesis:
chlorocyclooctane is also used in the production of other organic compounds, highlighting its versatility as a building block in organic chemistry.
Note: It is important to handle chlorocyclooctane with care due to its flammable nature and potential harmful effects, ensuring safety precautions are taken during its use.

InChI:InChI=1/C8H15Cl/c9-8-6-4-2-1-3-5-7-8/h8H,1-7H2

Upstream product

• 292-64-8 Cyclooctan 
• 931-88-4 cis-Cyclooctene 
• 696-71-9 cyclooctanol 
• 110-86-1 pyridine 
• 75-71-8 Dichlorodifluoromethane 
• 75-91-2 tert.-butylhydroperoxide 
• 80-15-9 Cumene hydroperoxide 
• 931-88-4 1,2-cyclooctene 

Downstream Products

• 6688-11-5 cyclooctylcarboxaldehyde 
• 4103-15-5 cyclooctanecarboxylic acid 
• 6713-50-4 Cyclooctylmethylketon 

Relevant articles and documents

Spectroscopic Analyses on Reaction Intermediates Formed during Chlorination of Alkanes with NaOCl Catalyzed by a Nickel Complex

The spectroscopic, electrochemical, and crystallographic characterization of [(Me,HPyTACN)NiII(CH3CN)2](OTf)2 (1) (Me,HPyTACN = 1-(2-pyridylmethyl)-4,7-dimethyl-1,4,7-triazacyclononane, OTf = CF3SO3) is described together with its reactivity with NaOCl. 1 catalyzes the chlorination of alkanes with NaOCl, producing only a trace amount of oxygenated byproducts. The reaction was monitored spectroscopically and by high resolution electrospray-mass spectrometry (ESI-MS) with the aim to elucidate mechanistic aspects. NaOCl reacts with 1 in acetonitrile to form the transient species [(L)NiII-OCl(S)]+ (A) (L = Me,HPyTACN, S = solvent), which was identified by ESI-MS. UV/vis absorption, electron paramagnetic resonance, and resonance Raman spectroscopy indicate that intermediate A decays to the complex [(L)NiIII-OH(S)]2+ (B) presumably through homolytic cleavage of the O-Cl bond, which liberates a Cl? atom. Hydrolysis of acetonitrile to acetic acid under the applied conditions results in the formation of [(L)NiIII-OOCCH3(S)]2+ (C), which undergoes subsequent reduction to [(L)NiII-OOCCH3(S)]2+ (D), presumably via reaction with OCl- or ClO2-. Subsequent addition of NaOCl to [(L)NiII-OOCCH3(S)]+ (D) regenerates [(L)NiIII-OH(S)]2+ (B) to a much greater extent and at a faster rate. Addition of acids such as acetic and triflic acid enhances the rate and extent of formation of [(L)NiIII-OH(S)]2+ (B) from 1, suggesting that O-Cl homolytic cleavage is accelerated by protonation. Overall, these reactions generate Cl? atoms and ClO2 in a catalytic cycle where the nickel center alternates between Ni(II) and Ni(III). Chlorine atoms in turn react with the C-H bonds of alkanes, forming alkyl radicals that are trapped by Cl? to form alkyl chlorides.

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A General Strategy for Aliphatic C-H Functionalization Enabled by Organic Photoredox Catalysis

Synthetic transformations that functionalize unactivated aliphatic C-H bonds in an intermolecular fashion offer unique strategies for the synthesis and late-stage derivatization of complex molecules. Herein we report a general approach to the intermolecular functionalization of aliphatic C-H bonds using an acridinium photoredox catalyst and phosphate salt under blue LED irradiation. This strategy encompasses a range of valuable C-H transformations, including the direct conversions of a C-H bond to C-N, C-F, C-Br, C-Cl, C-S, and C-C bonds, in all cases using the alkane substrate as the limiting reagent. Detailed mechanistic studies are consistent with the intermediacy of a putative oxygen-centered radical as the hydrogen atom-abstracting species in these processes.

Silica gel-mediated hydrohalogenation of unactivated alkenes using hydrohalogenic acids under organic solvent-free conditions

Silica gel-mediated hydrochlorination of unactivated alkenes using 35% hydrochloric acid under organic solvent-free conditions proceeded to give the corresponding chlorides in good yields. Hydrobromination or hydriodination using 47% hydrobromic acid or 55% hydriodic acid afforded the corresponding halides, respectively. Silica gel could be recycled five times without any significant loss of activities.