Decyl bromide

Decyl alcohol, dl6 Decyl bromide, b315 Decyl chloride, c94 Decylic acid, dl5 Decyl iodide, i29 Decyl mercaptan, dl4... 

Decyl bromide [112-29-8] Daphnia pulex EC50 (48-h) -1.13 Smith et ak, 1988... 

Alkylation, of diethyl malonate with 3-chlorocyclopentene, 32, 52 of diethyl methylmalonate with M-decyl bromide, 38, 49 of diethyl phthalimidomalonate,... 

Later Takahashi et al.19 have reported an alternative synthesis of the cyanooxirane (40a,b) by carrying out the reaction between decyl bromide and potassium cyanide in the presence of quaternary ammonium catalysts. Compounds prepared by this method are similar to those obtained by the Darzens condensation with benzaldehyde in a two-phase system.78... 

Fig. 2. Examples of nucleophilic substitution reactions performed in microemulsions. Scheme 1 synthesis of decyl sulfonate from decyl bromide and hydrogen sulfite. Scheme 2 synthesis of 2-hydroxyoctyl sulfonate from 1,2-epoxyoctane and hydrogen sulfite. Scheme 3 reaction of 4-nitrobenzylpyridine (NBP) with an alkyl halide (RX) followed by alkaline hydrolysis of the N-alkyl derivative (NBP-R+) formed. Scheme 4 a reaction involving displacement of the trinitrophenoxide ion by bromide...

Oh et al. [16] have demonstrated that a microemulsion based on a nonionic surfactant is an efficient reaction system for the synthesis of decyl sulfonate from decyl bromide and sodium sulfite (Scheme 1 of Fig. 2). Whereas at room temperature almost no reaction occurred in a two-phase system without surfactant added, the reaction proceeded smoothly in a micro emulsion. A range of microemulsions was tested with the oil-to-water ratio varying between 9 1 and 1 1 and with approximately constant surfactant concentration. NMR self-diffusion measurements showed that the 9 1 ratio gave a water-in-oil microemulsion and the 1 1 ratio a bicontinuous structure. No substantial difference in reaction rate could be seen between the different types of micro emulsions, indicating that the curvature of the oil-water interface was not decisive for the reaction kinetics. More recent studies on the kinetics of hydrolysis reactions in different types of microemulsions showed a considerable dependence of the reaction rate on the oil-water curvature of the micro emulsion, however [17]. This was interpreted as being due to differences in hydrolysis mechanisms for different types of microemulsions. 

Fig. 8. Reaction profiles for synthesis of sodium decyl sulfonate from decyl bromide and sodium sulfite in either a microemulsion or a two-phase system with or without added phase transfer agent (from [50])...

Fig. 9. Reaction steps involved in the synthesis of decyl sulfonate from decyl bromide and sodium sulfite using phase transfer catalysis. Q stands for tetrabutylammonium...

It has been shown that the addition of a small amount of the anionic surfactant sodium dodecyl sulfate (SDS) to a microemulsion based on nonionic surfactant increased the rate of decyl sulfonate formation from decyl bromide and sodium sulfite (Scheme 1 of Fig. 2) [59,60]. Addition of minor amounts of the cationic surfactant tetradecyltrimethylammonium gave either a rate increase or a rate decrease depending on the surfactant counterion. A poorly polarizable counterion, such as acetate, accelerated the reaction. A large, polarizable counterion, such as bromide, on the other hand, gave a slight decrease in reaction rate. The reaction profiles for the different systems are shown in Fig. 12. More recent studies indicate that when chloride is used as surfactant counterion the reaction may at least partly proceed in two steps, first chloride substitutes bromide to give decyl chloride, which reacts with the sulfite ion to give the final product [61]. 

Decyl bromide [112-29-8] M 221.2, b 117-118°/15.5mm, d 1.066. Shaken with H2SO4, washed with water, dried with K2CO3, and fractionally distd. 

Alkyl metals are not suitable for the metallation of tiiese compounds. For example, BuaU reacts at -78 C on the seletuum atom of selenonium salts and produces a novel organolithium in which the carb-aruonic center is more stabilized (Scheme 50, a and b), whereas alkylmagnesium bronudes and chlmides unexpectedly lead to decyl bromide and chloride respectively on reaction with decyl phenyl selenrme (Scheme 50, c). 

For example, reaction of n-decyl bromide with -butylmagnesium chloride... 

AI3-28586 1-Bromodecane Decane, 1-bromo- Decyl bromide 1-Oecyl bromide n-Oecyl bromide EINECS 203-955-3 NSC 8780. Chemical intermediate and solvent. Liquid mp = -29.2° bp 240.6° d = 1.0702 insoluble in H2O, soluble in CCI4, very soluble in EtOH, CHCI3 Ethicon Inc. Great Lakes Fine Chem. Hunpirey. 

Not too high-boiling alkyl bromides (up to C6) are distilled directly from the reaction mixture, distillation being continued until no more water-insoluble material passes over (about 1 h). The crude bromide, which contains alcohol, ether, etc., is separated from the aqueous phase of the distillate or the reaction mixture can be distilled in steam, a procedure that has proved valuable for isolation of w-butyl and /i-decyl bromide.908... 

Decyl bromide (475 g) and potassium cyanide (150 g) are heated under reflux on a water-bath for about 10 h in 96% ethanol (1.51) and water (250 ml). After cooling, the potassium bromide is filtered off, the ethanol is distilled off on a water-bath, and the residual oil is distilled under diminished pressure. The crude nitrile is purified by hydrolysis with concentrated hydrochloric acid in the cold, recrystallization of the resulting amide from ethanol, and removal of water therefrom by phosphoric oxide to give the nitrile (for details of these procedures see ref. 106, Vol. 8, pages 293, 330). The pure nitrile, b.p. 139.6-139.8°, is then obtained in 84% yield. 

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