533-98-2

Usage

Uses

Used in Chemical Synthesis:
1,2-Dibromobutane is used as a chemical intermediate for the production of various organic compounds. Its reactive bromine atoms make it a versatile building block for the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
1,2-Dibromobutane is used as a starting material for the synthesis of certain pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Research and Development:
1,2-Dibromobutane is employed in research and development for the study of various chemical reactions and mechanisms. The investigation of its reduction using Co(II) (N,N′-disalicylidene-ethylenediamine) catalyzed in DMF, as mentioned in the provided materials, is an example of how 1,2-DIBROMOBUTANE is utilized in scientific research to understand and optimize chemical processes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 3116, 1983 DOI: 10.1021/jo00166a041

InChI:InChI=1/C4H8Br2/c1-2-4(6)3-5/h4H,2-3H2,1H3

Upstream product

• 109-65-9 1-bromo-butane 
• 106-98-9 1-butylene 
• 107-00-6 but-1-yne 
• 2516-33-8 Cyclopropylmethanol 
• 78-76-2 s-butyl bromide 
• 593-71-5 Chloroiodomethane 
• 123-38-6 propionaldehyde 
• 7726-95-6 bromine 
• 109-69-3 n-Butyl chloride 
• 106-97-8 n-butane 
• 533-98-2 1,2-dibromobutane 
• 26256-82-6 (S)-2-bromo-butan-1-ol 
• 67-56-1 methanol 
• 616-27-3 1-chlorobutan-2-one 

Downstream Products

• 23074-36-4 2-bromobutene 
• 13814-27-2 1,2-butanediol diacetate 
• 106-98-9 1-butylene 
• 5408-86-6 2,3-dibromobutane 
• 584-03-2 1,2-dihydroxybutane 
• 4426-48-6 1,2-butanediamine 
• 3195-86-6 2-ethylthiirane 
• 78186-85-3 4-ethyl ethylene trithiocarbonate 
• 107-00-6 but-1-yne 
• 719-79-9 1,1-diphenylbutane 
• 31844-98-1 (E)/(Z)-1-bromo-1-butene 
• 1679-36-3 3-hexyn-2-one 
• 533-98-2 (S)-1,2-dibromobutane 
• 4096-21-3 N-phenylpyrrolidine 

Relevant academic research and scientific papers

Induced Fitting and Polarization of a Bromine Molecule in an Electrophilic Inorganic Molecular Cavity and Its Bromination Reactivity

Dodecavanadate, [V12O32]4? (V12), possesses a 4.4 ? cavity entrance, and the cavity shows unique electrophilicity. Owing to the high polarizability, Br2 was inserted into V12, inducing the inversion of one of the VO5 square pyramids to form [V12O32(Br2)]4? (V12(Br2)). The inserted Br2 molecule was polarized and showed a peak at 185 cm?1 in the IR spectrum. The reaction of V12(Br2) and toluene yielded bromination of toluene at the ring, showing the electrophilicity of the inserted Br2 molecule. Compound V12(Br2) also reacted with propane, n-butane, and n-pentane to give brominated alkanes. Bromination with V12(Br2) showed high selectivity for 3-bromopentane (64 %) among the monobromopentane products and preferred threo isomer among 2-,3-dibromobutane and 2,3-dibromopenane. The unique inorganic cavity traps Br2 leading the polarization of the diatomic molecule. Owing to its new reaction field, the trapped Br2 shows selective functionalization of alkanes.

Oxidative bromination of alkenes mediated with nitrite in ionic liquids

The oxidative bromination of C2-C8 alkenes with HBr-NaNO2-O2 in solutions of BMImBr, HMImBr or BMImBF 4 containing 16-28 wt% H2O was studied using volumetric method, GC-MS analysis, 14N NMR and UV-VIS spectroscopy. The optimal conditions to conduct the reaction at high selectivity for 1,2-dibromoalkanes in BMImBr were determined. The composition of ionic liquid affects the catalytic performance. Although in BMImBF4 the reaction runs with equal rate as in bromide ionic liquid, the fraction of bromohydrin in the reaction products increases to 20 %. Generated from NaNO2, NOx operated as a catalyst in the oxidation of Br- and was oxidized to catalytically inert NO3 - anions when complete conversion of HBr was attained. Graphical Abstract: Oxidative bromination of alkenes [Figure not available: see fulltext.]

Enantioselectivity of haloalkane dehalogenases and its modulation by surface loop engineering

In the loop: Engineering of the surface loop in haloalkane dehalogenases affects their enantiodiscrimination behavior. The temperature dependence of the enantioselectivity (lnE versus 1/T) of β-bromoalkanes by haloalkane dehalogenases is reversed (red data points) by deletion of the surface loop; the selectivity switches back when an additional single-point mutation is made. This behavior is not observed for -bromoesters.

CHLOROMETHYL-LITHIUM AND 1-CHLORO-2-METHYLPROP-1-ENYL-LITHIUM: USEFUL INTERMEDIATES IN THE SYNTHESIS OF UNSATURATED AND BIFUNCTIONALIZED COMPOUNDS

The reaction of in situ generated chloromethyl-lithium with ketones (5) at -78 deg C afforded, after lithiation with lithium naphthalenide at the same temperature, β-oxidoalkyl-lithium compounds (6), which on reaction with electrophiles (deuterium oxide, dimethyl disulphide, carbon dioxide, cyclohexanone, and allyl bromide) yielded bifunctionalized compounds (7).When the lithiation step was carried out with lithium powder and at temperatures ranging between -60 deg C and 20 deg C, the corresponding decomposition of intermediates (6) derived from aldehydes and ketones (5) took place spontaneously giving the corresponding terminal or exocyclic olefins (11) regioselectively.The use of in situ generated 1-chloro-2-methylprop-1-enyl-lithium as organolithium reagent in the addition to carbonyl compounds (5) at -110 deg C, followed by transformation of the resulting chlorohydrin (13) into the corresponding methyl ether (14) (successive treatment with sodium hydride and methyl iodide at 0-20 deg C) gave, after lithiation with lithium phenanthrenide at room temperature, the corresponding substituted cumulenes (12).

Bromochlorination of Alkenes with Dichlorobromate (1-) ion. IV. Regiochemistry of Bromochlorinations of Alkenes with Molecular Bromine Chloride and Dichlorobromate (1-) Ion

The regioselectivity of the addition of molecular bromine chloride to alkenes is dependent on both the steric and electronic effects of the alkyl substituent.In contrast, the regioselectivity of the addition of dichlorobromate (1-) ion to alkenes is controlled mainly by the steric effect of the substituent.

A reinvestigation of the vapor phase bromination of 2-bromobutane

The soltuion phase photobromination of 2-bromobutane yields 2,2-dibromobutane, meso-2,3-dibromobutane, dl-2,3-dibromo-dibromobutane, small amounts of 1,2-dibromobutane, and 2,2,3-tribromobutane.However, in the corresponding vapor phase bromination these products appear along with other polybrominated products.The yield of these polybromides increases with temperature.The increase in yield of the polyhalogenated materials is rationalized by considering the thermal instabilty of the β-bromoalkyl radical, which eliminates a bromine atom to form the corresponding alkene.It is demonstrated that in the vapor phase allylic bromination competes succesfully with bromine addition.Reaction schemes are suggested to explain the formation of polybromides.An explanation is also offered for the dicrepancy between these results and those of previously reported vapor phase work.

Alkyl Bromide Photobromination: Catalysis by Hydrogen Bromide and the Elimination-Readdition Pathway

In the photobromination of alkyl bromides, hydrogen bromide is shown to act as a catalyst and a kinetic study implies that two molecules of the acid are involved in catalysis.The catalysis is specific in two ways: only HBr is effective and it operates only with alkyl bromides having a β-hydrogen available for substitution.HBr favours the formation of 1,2-dibromides.This catalytic pathway is superimposed on the classical, uncatalysed mechanism.Isotopic labelling experiments show that an elimination-readdition pathway may also account for part of the reaction (maximum 20percent) but cannot explain the migration of bromine which is observed in the formation of β-dibromides.

SELECTIVITIES OF pi - AND sigma -SUCCINIMIDYL RADICALS IN SUBSTITUTION AND ADDITION REACTIONS. APPENDIX: RESPONSE TO WALLING, EL-TALIAWI, AND ZHAO.

A new method for studies of pi -succinimidyl (S// pi ) radicals is described, one that makes possible the study of reactions of this radical with a variety of substrates not accessible by the use of Br//2-NBS. NBS systems containing BrCCl//3 at mole fractions greater than 0. 3 show all the characteristics associated with S// pi behavior, and they function in the presence of olefins which serve as Br//2 scavengers. If CCl//4 is substituted for BrCCl//3, the system is clearly S// sigma . The S// pi behavior is contrasted with S// sigma and Br multiplied by (times) reactivities for H abstractions from a variety of substrates and for additions to tert-butylethylene, isobutylene, and 1,3-butadiene. In early-transition-state systems, for H transfer, the strength of the bond being broken and the strength of the bond being made are not the major factors in determining reactivities. The behavior in late-transition-state systems is influenced by both bond strengths. The S// pi radical shows intermediate behavior. These conclusions are supported by primary deuterium isotope effects for methylene chloride and chlororoform. The Appendix addresses a number of questions raised by the preliminary study of NBS reactions by Walling et al.

Hydrogenolysis of 3,5-Dimethoxybenzyl Bromide with n-Butylmagnesium Bromide

3,5-Dimethoxybenzyl bromide on coupling with n-butylmagnesium bromide furnishes 3,4-dimethoxytoluene in ca. 50percent yield.The formation of 3,5-dimethoxytoluene has been rationalized.