543-59-9

Usage

Safety Profile

Dangerous fire hazard when exposed to heat or flame; can react with oxidizing materials. Moderately explosive in the form of vapor when exposed to heat or flame. To fight fire, use foam, CO2, dry chemical. Dangerous; when heated to decomposition it emits

InChI:InChI=1/C5H11Cl/c1-2-3-4-5-6/h2-5H2,1H3

Upstream product

• 632-02-0 3-chloropropyl p-toluenesulfonate 
• 60-29-7 diethyl ether 
• 925-90-6 ethylmagnesium bromide 
• 71-41-0 pentan-1-ol 
• 109-66-0 pentane 
• 16849-82-4 bis(pentyloxy)methane 
• 67-66-3 chloroform 
• 110-05-4 di-tert-butyl peroxide 
• 62101-23-9 n-pentyl chlorosulfite 
• 3397-76-0 N,N-Dimethylformamide Hydrochloride 
• 96449-48-8 pentyldiphenylbismutane 
• 94953-27-2 dipentyl (trichloromethyl)phosphonite 
• 628-17-1 amyl iodide 
• 2344-80-1 Chloromethyltrimethylsilane 

Downstream Products

• 91352-41-9 5-tert.-Amyl-brenzschleimsaeure-methylester 
• 87590-44-1 sesamyl n-pentylether 
• 2761-24-2 amyltriethoxysilane 
• 17957-65-2 (n-am)2Si(Oet)2 
• 628-71-7 1-Heptyne 
• 1595-10-4 1-n-hexyl-2-methylbenzene 
• 1595-01-3 1-hexyl-4-methyl-benzene 
• 66923-44-2 (2,4-dinitro-phenyl)-pentyl sulfide 
• 6249-76-9 N,N-dipentylaniline 
• 19692-40-1 2-methyl-2-phenyl-heptanenitrile 
• 628-73-9 hexanenitrile 
• 628-63-7 1-pentyl acetate 
• 63017-66-3 n-pentyl phenyl selenide 
• 538-68-1 pentylbenzene 

Relevant academic research and scientific papers

Highly selective halogenation of unactivated C(sp3)-H with NaX under co-catalysis of visible light and Ag@AgX

The direct selective halogenation of unactivated C(sp3)-H bonds into C-halogen bonds was achieved using a nano Ag/AgCl catalyst at RT under visible light or LED irradiation in the presence of an aqueous solution of NaX/HX as a halide source, in air. The halogenation of hydrocarbons provided mono-halide substituted products with 95% selectivity and yields higher than 90%, with the chlorination of toluene being 81%, far higher than the 40% conversion using dichlorine. Mechanistic studies demonstrated that the reaction is a free radical process using blue light (450-500 nm), with visible light being the most effective light source. Irradiation is proposed to cause AgCl bonding electrons to become excited and electron transfer from chloride ions induces chlorine radical formation which drives the substitution reaction. The reaction provides a potentially valuable method for the direct chlorination of saturated hydrocarbons.

A mild method for the replacement of a hydroxyl group by halogen. 1. Scope and chemoselectivity

α-Chloro-, bromo- and iodoenamines, which are readily prepared from the corresponding isobutyramides have been found to be excellent reagents for the transformation of a wide variety of alcohols or carboxylic acids into the corresponding halides. Yields are high and conditions are very mild thus allowing for the presence of sensitive functional groups. The reagents can be easily tuned allowing therefore the selective monohalogenation of polyhydroxylated molecules. The scope and chemoselectivity of the reactions have been studied and reaction mechanisms have been proposed.

Palladium nanoparticle catalysts in ionic liquids: Synthesis, characterisation and selective partial hydrogenation of alkynes to Z-alkenes

The simple heating (120 °C) of Pd(OAc)2 in 1-butyronitrile-3-methylimidazolium-N-bis(trifluoromethane sulfonyl)imide ((BCN)MI·NTf2) under reduced pressure leads to the formation of stable and small-sized Pd(0)-NPs (diameter: 7.3 ± 2.2 nm). These metal nanoparticles were characterised by means of TEM, HRTEM and XPS analysis techniques. Moreover, the potential for partial hydrogenation of alkynes in multiphase systems was evaluated. The hydrogenation of internal alkynes at 25 °C and under 1 bar of hydrogen yields Z-alkenes (up to 98% selectivity). Application of higher hydrogen pressure (4 bar) in these reactions always led to the formation of alkanes without the detection of any alkenes. TOF values were attained up to 1282 h-1 with a good recyclability of the system which does not lose its activity for at least 4 runs. The Royal Society of Chemistry 2011.

Synthesis of chlorothioformates from xanthates

The Vilsmeier reagent derived from N-formylmorpholine produces chlorothioformates from primary and secondary alkyl xanthates. The major side products are the corresponding alkyl chlorides. Secondary alkyl chlorothioformates give lower yields due to their instability. Treating xanthates with other common chlorinating agents (oxalyl chloride, thionyl chloride) gives only dialkyl thiodicarbonates. Georg Thieme Verlag Stuttgart.

Oxidation of monohydric and dihydric alcohols with CCl4 catalyzed by molybdenum compounds

Mo(CO)6 catalyzed oxidation of alcohols and diols with tetrachloromethane. Primary oxidation products in reaction of alcohols with CCl4 are alkyl hypochlorites, and final products depending on the structure of initial alcohol are aldehydes (as acetals), ketones, chloroketones, and esters.

Direct halogenation of alcohols and their derivatives with tert-Butyl halides in the ionic liquid [pmIm]Br under sonication conditions - A novel, efficient and green methodology

A novel halogenating reagent system for direct halogenation of alcohols has been developed. tert-Butyl bromide, chloride and iodide in combination with the ionic liquid [pmIm]Br have been found to convert alcohols into the corresponding bromides, chlorides and iodides under sonication conditions (or heating) in good yields. Although a variety of primary and secondary alcohols participated in this reaction without any difficulty, tertiary alcohols remained inert. Several alcohol derivatives such as OTMS, OTBDMS, OAc, OTS and OTHP are also transformed into the corresponding halides in one-pot fashion by this procedure. A plausible rationale for this transformation is also presented. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Generation of alkyl hypochlorites in oxidation of alcohols with carbon tetrachloride catalyzed by vanadium and manganese compounds

Primary alcohols and diols with various structures were subjected to transformations into esters, aldehydes, ketones, and lactones under the action of carbon tetrachloride in the presence of manganese compounds (MnCl 2, MnO2, Mn(OAc)2, Mn(acac)3) and vanadium compounds (VCl5, V2O5, VO(acac) 2) as catalysts. These transformation proceeded with the involvement of alkyl hypochlorites, which were generated in the course of oxidation of alcohols with carbon tetrachloride catalyzed by manganese or vanadium compounds. The optimum molar ratios between the catalyst and reagents were determined, and the reaction conditions for the highly selective synthesis of esters, aldehydes, ketones, and lactones from alcohols were found.

New versatile halogenating reagents for hydroxy groups

Two new halogenating reagents, viz. allyltriphenoxyphosphonium bromide (ATPB) and allyltriphenoxyphosphonium chloride (ATPC) have been prepared and characterised. These have been evaluated for their potential application in bromination/ chlorination of a variety of compounds including aliphatic straight chain alcohols, branched chain alcohols and also 3′- and 5′-hydroxy groups of deoxyribonucleosides.

BiX3 as an efficient and selective reagent for the halogen exchange reaction

Bismuth halides are efficient and selective reagents in the halogen exchange reactions carried out under mild conditions. This rapid, high yield reaction proceeds mainly with retention of configuration.