999-07-5

Usage

Uses

Used in Laboratory and Scientific Research:
4-CHLOROOCTANE is used as a solvent for its ability to dissolve a wide range of substances, facilitating numerous laboratory processes and scientific research applications.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 4-CHLOROOCTANE is utilized as a crucial intermediate in the synthesis of various medications, contributing to the development of new drugs and therapies.
Used in Pesticide Manufacturing:
4-CHLOROOCTANE plays a significant role in the production of pesticides, acting as an intermediate to help create effective and targeted pest control solutions.
Used in Organic Chemical Synthesis:
This chloroalkane is employed as an intermediate in the synthesis of other organic chemicals, highlighting its importance in the chemical industry for creating a diverse array of products.

InChI:InChI=1/C8H17Cl/c1-3-5-7-8(9)6-4-2/h8H,3-7H2,1-2H3/t8-/m1/s1

Upstream product

• 101883-01-6 bis-[(1-propyl-pentyloxy)-methyl]-ether 
• 111-65-9 octane 
• 4128-31-8 rac-octan-2-ol 
• 1174658-48-0 C₁₇H₂₃NO₃S 
• 1309251-35-1 C₁₃H₂₁NO₃S 
• 5978-70-1 (R)-Octan-2-ol 
• 56772-63-5 (R)-octan-2-yl methanesulfonate 
• 592-99-4 4-octene 
• 6169-06-8 (S)-2-Octanol 
• 34817-25-9 (S)-1-methylheptyl tosylate 
• 589-62-8 octan-4-ol 
• 1174658-47-9 C₁₇H₂₃NO₃S 
• 1174658-46-8 C₂₀H₃₂O₇S 
• 1028-12-2 2-Octyl tosylate 

Relevant academic research and scientific papers

Metal-free regioselective hydrochlorination of unactivated alkenes via a combined acid catalytic system

A combined acid HCl/DMPU-acetic acid catalytic system was used in the hydrochlorination of a wide range of unactivated alkenes. This hydrochlorination strategy is remarkably greener than previous reported methods in terms of high atom efficiency, no toxic waste generated and metal-free process. The higher efficiency, compared with other commercially available HCl reagents, was augmented by the good regioselectivity and functionality tolerance found. A stepwise mechanism for this hydrochlorination process was proposed based on kinetic studies.

Stereoretentive chlorination of cyclic alcohols catalyzed by titanium(IV) tetrachloride: Evidence for a front side attack mechanism

A mild chlorination reaction of alcohols was developed using the classical thionyl chloride reagent but with added catalytic titanium(IV) chloride. These reactions proceeded rapidly to afford chlorination products in excellent yields and with preference for retention of configuration. Stereoselectivities were high for a variety of chiral cyclic secondary substrates including sterically hindered systems. Chlorosulfites were first generated in situ and converted to alkyl chlorides by the action of titanium tetrachloride which is thought to chelate the chlorosulfite leaving group and deliver the halogen nucleophile from the front face. To better understand this novel reaction pathway, an ab initio study was undertaken at the DFT level of theory using two different computational approaches. This computational evidence suggests that while the reaction proceeds through a carbocation intermediate, this charged species likely retains pyramidal geometry existing as a conformational isomer stabilized through hyperconjugation (hyperconjomers). These carbocations are then essentially "frozen" in their original configurations at the time of nucleophilic capture.

Iron(III)-catalyzed halogenations by substitution of sulfonate esters

A novel halogenation reaction from sulfonates catalyzed by iron(III) is described. The reaction can be performed as a stoichiometric or a catalytic version. This reaction provides a convenient strategy for the efficient access to structurally diverse secondary chlorides, bromides and iodides. The stereochemical course of the reaction is governed by the substrate and the experimental conditions. Secondary alcohols modified as quisylates or pysylates are substantially more reactive. Aliphatic quisylates proceed with overall inversion of configuration under catalytic conditions. Chemoselectivity in bismesylates was observed in favour of the secondary mesylate. Additionally, based on the experimental results, a possible catalytic cycle for the halogenation has been proposed.

Clarification of the stereochemical course of nucleophilic substitution of arylsulfonate-based nucleophile assisting leaving groups

(Chemical Equation Presented) Secondary alcohols modified as tosylates, PEG-sulfonates, or quisylates undergo inversion of configuration at the reacting center when treated with lithium halide in acetone at reflux, where the PEG-sulfonates and quisylates are substantially more reactive. In sterically hindered cases, elimination is a competing process. In contrast, when treated with TiCl4, simple secondary sulfonates give chloride products with partial inversion of configuration. Any observed retention of configuration in a given alkyl sulfonate substrate under these conditions is likely due to neighboring group participation or diastereoselective attack on a carbocation (or ion pair) rather than an SNi mechanism.

Reactivity of bismuth(III) halides towards alcohols. A tentative to mechanistic investigation

The reactivity of bismuth(III) halides (BiX3; X=Cl, Br and I) towards a series of alcohols has been investigated. Three different reactions have been studied, namely: halogenation, dehydration and etherification. The behaviour of these bismuth derivatives was found to depend on the nature of the halide bonded to the bismuth atom. Their reactivities can be interpreted on the basis of the Hard and Soft Acids and Bases (HSAB) principle. A mechanism is proposed which involves the formation of a complex of the alcohol with Bi(III).

Activation of the silicon-halogen bond by bismuth (III) halides. Halogenation of alcohols: prospective and mechanism

In the presence of catalytic amount of BiCl3, chloromethylsylanes can be used as chlorinating agents for alcohols, and as chloro-dealkylating agents for silyl ethers and carboxylic and sulfonic esters.The chlorination of (R)-(-)-octan-2-ol and the (R)-(-)-2-mesyloctane by TMSCl gave predominantly the (S)-(+)-2-chlorooctane with inversion of configuration at secondary carbon.According to the class of alcohol, the mechanism involves SN2, SN2' or SN1 processes.This new activation of the Si-Cl bond, probably trough a Si-Cl...BiCl3 interaction gives a hard-soft reagent that can generate a silicenium cation, was also observed with Me3SiBr, BiBr3 and Me3SiI, BiI3 systems.The reaction is also presented as a possible alcoholysis of chlorosilanes, which can lead to siloxanes in non-aqueous conditions. catalysis / halogenation / alcohol / ester / silyl ether / chlorosilane / chlorotrimethylsilane / bromotrimethylsilane / iodotrimethylsilane / siloxane / bismuth (III) halide

CHLORIERENDE METHYLIERUNG VON ALDEHYD- UND KETOGRUPPEN MIT NIOB-REAGENZIEN SOWIE AUFKLAERUNG DES MECHANISMUS

The reagents MeNbCl4 and Me2NbCl3, applied as isolated pure compounds, react with ketones in preparatively useful yields according to RR'CO -> RR'C(Cl)CH3.Whereas benzaldehyde reacts with MeNbCl4 analogously, the aliphatic aldehyde heptanal forms beside the expected product two cinechlorination products, indicating a mechanism via radicals.MeNbCl4 is highly aldehyde-vs.-ketone selective.Conversely, high ketone-vs.-aldehyde selectivity is achievable by application of MeNbCl4*PPh3 or NbCl5*PPh3 + 1.5 Me2Zn.