4883-87-8

Upstream product

• 589-98-0 rac-3-octanol 
• 455-16-3 p-toluenesulfonyl fluoride 
• 904922-21-0 3-(trimethylsilyloxy)octane 
• 27770-99-6 R(-)-octyl tosylate 
• 76-05-1 trifluoroacetic acid 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 14850-22-7 cis-3-octene 
• 14919-01-8 (E)-3-octene 
• 7642-04-8 cis-2-octene 
• 13389-42-9 trans-2-Octene 
• 999-64-4 3-bromooctane 
• 1117-79-9 3-chlorooctane 

Relevant academic research and scientific papers

Structure-odor correlations in homologous series of alkanethiols and attempts to predict odor thresholds by 3d-qsar studies

Homologous series of alkane-1-thiols, alkane-2-thiols, alkane-3-thiols, 2-methylalkane-1-thiols, 2-methylalkane-3-thiols, 2-methylalkane-2-thiols, and alkane-1,??-dithiols were synthesized to study the influence of structural changes on odor qualities and odor thresholds. In particular, the odor thresholds were strongly influenced by steric effects: In all homologous series a minimum was observed for thiols with five to seven carbon atoms, whereas increasing the chain length led to an exponential increase in the odor threshold. Tertiary alkanethiols revealed clearly lower odor thresholds than found for primary or secondary thiols, whereas neither a second mercapto group in the molecule nor an additional methyl substitution lowered the threshold. To investigate the impact of the SH group, odor thresholds and odor qualities of thiols were compared to those of the corresponding alcohols and (methylthio)alkanes. Replacement of the SH group by an OH group as well as S-methylation of the thiols significantly increased the odor thresholds. By using comparative molecular field analysis, a 3D quantitative structure-activity relationship model was created, which was able to simulate the odor thresholds of alkanethiols in good agreement with the experimental results. NMR and mass spectrometric data for 46 sulfur-containing compounds are additionally supplied.

A facile and green protocol for nucleophilic substitution reactions of sulfonate esters by recyclable ionic liquids [bmim][X]

Ionic liquids [bmim][X] (X = Cl, Br, I, OAc, SCN) are highly efficient reagents for nucleophilic substitution reactions of sulfonate esters derived from primary and secondary alcohols. The counter anions (X-) of the ionic liquids, [bmim][X], effectively replace the sufonates affording the corresponding substitution products such as alkyl halides, acetates, and thiocyanides in excellent yields. The newly developed protocol is very environmentally attractive because the reactions use stoichiometric amounts of ionic liquids as sole reagents in most cases and do not require additional solvents, any other activating reagents, non-conventional equipment, or special precautions. Moreover, these ionic liquids can be readily recycled without loss of reactivity, making the whole process greener.

A facile and green protocol for nucleophilic substitution reactions of sulfonate esters by recyclable ionic liquids [bmim][X]

Ionic liquids [bmim][X] (X = Cl, Br, I, OAc, SCN) are highly efficient reagents for nucleophilic substitution reactions of sulfonate esters derived from primary and secondary alcohols. The counter anions (X-) of the ionic liquids, [bmim][X], effectively replace the sufonates affording the corresponding substitution products such as alkyl halides, acetates, and thiocyanides in excellent yields. The newly developed protocol is very environmentally attractive because the reactions use stoichiometric amounts of ionic liquids as sole reagents in most cases and do not require additional solvents, any other activating reagents, non-conventional equipment, or special precautions. Moreover, these ionic liquids can be readily recycled without loss of reactivity, making the whole process greener. Georg Thieme Verlag KG Stuttgart · New York.

Amphiphilic organocatalyst for schotten-baumann-type tosylation of alcohols under organic solvent free condition

A Tosylation of primary alcohol with tosyl chloride was performed effectively with an W-hexadecylimidazole catalyst in water containing K 2CO3 aggregation of the catalyst carrying a hydrophobic methylene chain worked as a substitute for organic solvent.

An efficient organocatalyzed interconversion of silyl ethers to tosylates using DBU and p-toluenesulfonyl fluoride

A mild and efficient interconversion from silyl ethers to sulfonates esters is reported with good yields. This silyl-sulfonyl exchange proceeds readily in acetonitrile at room temperature in the presence of p-toluenesulfonyl fluoride and a catalytic amount of 1,8-diazabicyclo[5.4.0]undec-7ene (DBU). This method can be used with trimethysilyl (TMS), triethylsilyl (TES) and tert-butyldimethylsilyl (TBDMS) ethers. Georg Thieme Verlag Stuttgart.

General, robust, and stereocomplementary preparation of β-ketoester enol tosylates as cross-coupling partners utilizing TsCl-N-methylimidazole agents

(Chemical Equation Presented) We have developed a general, robust, and cost-effective method for the (E)- or (Z)-stereocomplementary enol tosylation of β-ketoesters using TsCl-N-methylimidazole (NMI)-Et3N or LiOH. TsCl coupled with NMI formed a

Facile and practical methods for the sulfonylation of alcohols using Ts(Ms)Ci and Me2N(CH2)(n)NMe2 as a key base

Several alcohols were smoothly and practically tosylated by two Methods A and B. Method A uses the TsCl/Me2N(CH2)(n)NMe2 (n = 3 or 6) reagent and Method B uses TsCl/Et3N/catalytic Me2N(CH2)

Practical and efficient methods for sulfonylation of alcohols using Ts(Ms)Cl/Et3N and catalytic Me3N · HCl as combined base: Promising alternative to traditional pyridine

Several alcohols were smoothly and practically tosylated by two methods A and B. Method A uses the TsCl/Et3N (1.5 - 2.5 equiv)/cat. Me3N · HCl (0.1 - 1.0 equiv) reagent. Compared with the traditional Py-solvent method, the method A has merits of its much higher reaction rate, operational simplicity, economy in the use of the amine, and circumvention of the undesirable side reaction from R-OTs to R-CL. Method B uses TsCl/KOH [or Ca(OH)2]/cat. Et3N (0.1 equiv)/cat. Me3N · HCl (0.1 equiv) as the reagent, which will be suited for practical and large scale production for primary alcohols. On both methods A and B, a clear joint action of Et3N and Me3N · HCl catalysts was observed. 1H NMR measurements support the proposed mechanism of the catalytic cycle. Related methanesulfonylation using Et3N and cat. Me3N · HCl in toluene solvent also successfully proceeded, wherein the clear joint action was also observed.

Stereochemistry of Trifluoroacetolysis of Optically Active 2-Butyl Tosylate. A Test for Hydrogen Bridging

Trifluoroacetolysis of (R)-(-)-2-butyl tosylate at 25 deg C gives 2-butyl trifluoroacetate with 7 +/- 1percent net inversion.The ratio of the polarimetric and spectrophotometric rate constants is 1.55, and this decreases to 1.05 in the presence of 0.125 M NaO2CCF3.These results are most simply and plausibly interpreted in terms of formation of an ion pair consisting of an open 2-butyl cation and a tosylate anion which gives racemized tosylate by ion-pair return and by elimination/readdition, with competitive nucleophilic solvent attack with a small overall preference for substitution on the side opposite the anion.A published proposal based on deuterium labeling studies that a hydrogen-bridged butyl cation is the predominant intermediate in this reaction does not give a simple prediction of these results.