1,4-Dibromobutane: Properties, Cycloalkylation Role, and Cyclopentane Derivative Synthesis

Aug 29,2025

1,4-Dibromobutane is a colorless to pale yellow liquid. It is often noted for its transparency and is generally free from suspended particles. 1,4-Dibromobutane reaction with atactic poly(2-vinylpyridine) leads to the formation of long-range 3D molecular ordering in polymer chains. It was used to investigate the metabolism of two halopropanes: 1,3-dichloropropane and 2,2-dichloropropane. It was used as reagent during the synthesis of diazadioxa oxovanadium(IV) macrocyclic complexes.

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Cycloalkylation of phenylacetonitrile with 1,4-dibromobutane

The problems associated with the organic bi-phase reactions were not solved until Jarrouse discovered the catalyzing effect of quaternary ammonium salt in the aqueous/organic phase reaction systems. The quaternary ammonium salt, which served as a phase-transfer catalyst in the two-phase reactions, has then emerged as an important tool and has become a fascinating subject of research interest. This paper reports a kinetic study of the cycloalkylation of phenylacetonitrile (PAN) with an excess of 1,4-dibromobutane using the new water soluble Diquat, Dq-Br, under PTC conditions and also proposes a suitable mechanism. The effect of varying stirring speed on the rate of cycloalkylation of PAN with 1,4-dibromobutane using the new phase transfer reagent, Dq-Br, was studied in the range 200–800 rpm. An increase in the rate of reaction was noticed as the stirring speed was enhanced. The effect of varying stirring speed was well documented for the interfacial mechanisms which are transfer rate limited (the rate constants increase with stirring) below a given stirring speed (600–800 rpm) and intrinsic reaction rate limited (the rate constants are nearly a constant value) above this stirring speed.[1]

The kinetic experiments were performed in an ordinary smooth-walled 150 ml three-necked flask fitted with a flat-bladed stirring paddle and reflux condenser. 1,4-Dibromobutane (66.98 mmol) preheated to 70°C was added to the reaction mixture. The stirring speed was adjusted to 500 rpm. The samples from the organic layer were withdrawn by a hypodermic syringe and analyzed by gas chromatography (Shimadzu GC 14B with flame ionization detector using 100% methylpolysiloxane, db 1 capillary column, 15 m × 0.525 mm and nitrogen as carrier gas). The reaction was followed by estimating the disappearance of PAN. The effect of varying stirring speed on the rate of cycloalkylation of PAN with 1,4-dibromobutane using the new phase transfer reagent, Dq-Br, was studied in the range 200–800 rpm. An increase in the rate of reaction was noticed as the stirring speed was enhanced.

Synthesis of cyclopentane derivatives in the presence of 1,4-dibromobutane

The cathodic electrolysis of compounds with an activated methylene group in the presence of 1,4-dibromobutane leads to 1,1-disubstituted cyclopentanes. In previous work, we have shown that the cathodic electrolysis of compounds with an activated methylene group (CAMG) in 1,2-dichloroethane leads to cyclopropane derivatives. In a continuation of this work, we studied the feasibility of the cathodic synthesis of five- membered alicyclic compounds upon the electrolysis of compounds with an activated methylene group in the presence of 1,4-dibromobutane. The electrolysis was carried out in a diaphragm cell. A 35 cm 2 sheet of platinum foil treated in concentrated nitric acid and annealed on a Bunsen burner served as the cathode. A 2 x 10-mm vitreous carbon plate served as the anode. The catholyte consisted of 37 ml ace- tonitrile, 3 ml 1,4-dibromobutane, 3 g Bu4NBr , and 5 mmoles CAMG [acetylacetone (I), malono- dinitrile (II), ethyl acetoacetate (III), ethyl cyanoacetate (IV), diethyl malonate (V), ethyl phenylacetate (VI), and phenylacetonitrile (VII)]. The anolyte consisted of 20 ml acetonitrile, 1.5 g Bu4NBr , and 2 ml cyclohexene used as a trap for the Br 2 formed. The electrolysis was carried out at 20~ with rapid stirring using a magnetic stirrer in a gal- vanostatic mode (I - 80 mA, Q - 2.2 F per mole starting CAMG). The catholyte was analyzed by gas-liquid chromatography during the electrolysis on a Chrom 5 chromatograph using a 2.4-m column packed with SE-30 on Chromaton.

On the whole, the yield of the cyclopentane derivatives is significantly greater than for the cyclopropane derivatives. This discrepancy is related to the great- er difficulty in reducing 1,4-dibromobutane in comparison with 1,2-dichloroethane, in which the vicinal halogen atoms are relatively easily lost on the cathode with the formation of ethylene. This process, which competes with reduction of the CH-acid (see above), de- creases the yield of the cyclic product. Thus, the cathodic electrolysis of several compounds with an activated methylene group in the presence of 1,4-dibromobutane may be used for the preparation of l,l-disubstituted cyclopentanes in addition to various chemical reactions [2].

References

[1]Jayachandran, J. P., & Wang, M. - L. (2000). Cycloalkylation of phenylacetonitrile with 1,4 - dibromobutane catalyzed by aqueous sodium hydroxide and a new phase transfer reagent, Dq - Br. Applied Catalysis A: General, 198(1 - 2), 127 - 137. https://www.sciencedirect.com/science/article/pii/S0926860X99005037

[2]Tatarinova, V. I., Vasil’ev, A. A., & Petrosyan, V. A. (1990). Synthesis of cyclopentane derivatives in the cathodic electrolysis of compounds with an activated methylene group in the presence of 1,4 - dibromobutane. Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science, 39, 2399 - 2401. https://link.springer.com/article/10.1007/BF00958865

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