5787-31-5

Usage

Uses

Used in Organic Synthesis Industry:
(±)-2-Bromobutane is used as a solvent for facilitating various chemical reactions in organic synthesis. Its properties enable it to dissolve a wide range of organic compounds, making it a versatile component in the synthesis process.
Used in Chemical Production:
(±)-2-Bromobutane is used as a reagent in the production of other chemicals. Its reactivity and ability to participate in different types of chemical reactions make it a valuable intermediate in the synthesis of a variety of chemical products.
Used in Pharmaceutical Manufacturing:
(±)-2-Bromobutane is used as an intermediate in the manufacturing of pharmaceuticals. Its versatility in chemical reactions allows it to be a key component in the synthesis of various drug molecules.
Used in Pesticide Production:
(±)-2-Bromobutane is used in the production of pesticides. Its chemical properties make it suitable for use in the creation of active ingredients or as a component in the formulation of pesticide products.
Used in Synthesis of Other Organic Compounds:
(±)-2-Bromobutane is used as an intermediate in the synthesis of other organic compounds. Its ability to undergo elimination, substitution, and nucleophilic substitution reactions makes it a useful building block in the creation of a wide range of organic molecules.

Upstream product

• 109-65-9 1-bromo-butane 
• 106-98-9 1-butylene 
• 78-86-4 s-butyl chloride 
• 78-77-3 Isobutyl bromide 
• 2465-56-7 methylene 
• 75-26-3 isopropyl bromide 
• 118725-88-5 dibromophosphoric acid sec-butyl ester 
• 78-92-2 iso-butanol 
• 590-18-1 (Z)-2-Butene 
• 7581-97-7 2,3-dichlorobutane 
• 2211-67-8 racemic 2,3-dichlorobutane 
• 105-46-4 sec-Butyl acetate 
• 115-10-6 Dimethyl ether 
• 109-69-3 n-Butyl chloride 

Downstream Products

• 25991-45-1 1-(1-methylpropyl)piperidine 
• 101582-56-3 N-sec-butyl-toluene-4-sulfonanilide 
• 61248-62-2 (+/-)-2-mesityloxy-butane 
• 101286-68-4 (3-sec-butoxy-phenyl)-phenyl-amine 
• 51241-44-2 (+/-)-2-m-tolyloxy-butane 
• 51241-46-4 p-tolyl s-butyl ether 
• 18936-17-9 2-methylbutanenitrile 
• 10574-17-1 but-2-yl phenyl ether 
• 10108-61-9 N-(1-methylpropyl)phthalimide 
• 924-43-6 sec-butyl nitrite 
• 600-24-8 2-nitrobutane 
• 109-65-9 1-bromo-butane 
• 5408-86-6 2,3-dibromobutane 
• 533-98-2 1,2-dibromobutane 

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.

METHOD FOR PRODUCING FLUORINATED HYDROCARBON

PROBLEM TO BE SOLVED: To provide an industrially advantageous method for producing a fluorinated hydrocarbon such as 2-fluorobutane useful as etching gas for a dry etching process. SOLUTION: There is provided a method for producing a fluorinated hydrocarbon represented by formula (3) by bringing an ether compound represented by formula (1) into contact with an acid fluoride represented by formula (2) in a halogenated hydrocarbon solvent in the presence of a metal halide represented by formula (4): MX3 (M represents a metal atom; X represents a chlorine atom or a bromine atom) (R1 and R2 each independently represent an alkyl group having 1-3 carbon atoms; R1 and R2 may be bonded to form a ring structure; R3 represents H, a methyl group or an ethyl group; R4 and R5 each independently represent a methyl group or an ethyl group.) SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Iron-copper cooperative catalysis in the reactions of alkyl grignard reagents: Exchange reaction with alkenes and carbometalation of alkynes

Iron-copper cooperative catalysis is shown to be effective for an alkene-Grignard exchange reaction and alkylmagnesiation of alkynes. The Grignard exchange between terminal alkenes (RCH=CH2) and cyclopentylmagnesium bromide was catalyzed by FeCl3 (2.5 mol %) and CuBr (5 mol %) in combination with PBu3 (10 mol %) to give RCH2CH 2MgBr in high yields. 1-Alkyl Grignard reagents add to alkynes in the presence of a catalyst system consisting of Fe(acac)3, CuBr, PBu3, and N,N,N″,N″-tetramethylethylenediamine to give β-alkylvinyl Grignard reagents. The exchange reaction and carbometalation take place on iron, whereas copper assists with the exchange of organic groups between organoiron and organomagnesium species through transmetalation with these species. Sequential reactions consisting of the alkene-Grignard exchange and the alkylmagnesiation of alkynes were successfully conducted by adding an alkyne to a mixture of the first reaction. Isomerization of Grignard reagents from 2-alkyl to 1-alkyl catalyzed by Fe-Cu also is applicable as the first 1-alkyl Grignard formation step.

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.

Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone as a new, selective and neutral system for the facile conversion of alcohols, thiols and selenols to alkyl halides in the presence of halide ions

A mixture of triphenylphosphine (Ph3P) and 2,3-dichloro-5,6-dicyanobenzoquinone in CH2Cl2 affords a complex which in the presence of R4NX (X=Cl, Br, I) converts alcohols, thiols and selenols into their corresponding alkyl halides in high yields at room temperature. The method is highly selective for the conversion of 1° alcohols in the presence of 2° ones and also 1° and 2° alcohols in the presence of 3° alcohols, thiols, epoxides, trimethylsilyl- and tetrahydropyranyl ethers, 1,3 dithianes, disulfides, and amides.

A new supported reagent for the photochemical generation of radicals in solution

matrix presented A new polymer-supported radical source was developed by loading an N-hydroxy thiazole 2(3)-thione on a Wang resin. This new supported reagent can be employed for a solid-phase version of the Hunsdiecker reaction or to liberate free alkoxy radicals, in a variant of the "catch and release" technique, under very mild conditions (irradiation with a discharge lamp) and simplifying the purification procedure.

Mild conversion of alcohols to alkyl halides using halide-based ionic liquids at room temperature

Formula presented Alcohols were efficiently converted to alkyl halides using 1-n-butyl-3-methylylimidazolium halides (ionic liquids) in the presence of Bronsted acids at room temperature. The alkyl halide products were easily isolated from the reaction mixture via simple decantation or extraction, and the 1-n-butyl-3-methylimidazolium cation could be recycled for further uses.

Complete inversion of configuration in aliphatic nucleophilic substitution reactions with small inner-sphere stabilization

The stereochemistry of the nucleophilic reaction of the enolate anion of 1,4-dihydro-4-methoxycarbonyl-1-methylpyridine (1-) with (R)-(-)- and (S)-(+)-2-bromobutane has been investigated and correlated with the inner-sphere stabilization of the reactions calculated from the ratio kSUB/kET, where kSUB is the rate of substitution and kET the expected rate of electron transfer. It was shown that 1- reacts with 2-bromobutane with nearly complete inversion of configuration (99.7%). A complete shift in stereochemistry of the nucleophilic reactions of 1- with alkyl halides from racemization to complete inversion is induced by a small increase in the inner-sphere stabilization of the transition state from 0 to 3 kcal mol-1. The results in this work suggest that the SN2 inversion process in general is extremely sensitive towards inner-sphere stabilization. Acta Chemica Scandinavica 1998.

Functionalization of saturated hydrocarbons by aprotic superacids 4. Ionic bromination of ethane and other alkanes and cycloalkanes with molecular bromine in the presence of systems based on polyhalomethanes and AlBr3 under mild conditions

Aprotic organic superacids CBr4 · 2AlBr3, CBr4 · AlBr3, · CCl4 · 2AlBr3, CCl4 · 2AlBr3, and C6F5CF3 · 2AlBr3 efficiently catalyze the bromination of alkanes and cycloalkanes with Br2. Ethane is selectively brominated at 55-65 °C to give mostly 1,2-dibromoethane (stoichiometric reaction). Propane, butane, cyclopentane, cyclohexane, and methyl-cyclopentane react with Br2 at -40 to -20 °C with good selectivity affording monobromides in high yields (catalytic reactions).

Ionic Bromination of Ethane and Other Alkanes (Cycloalkanes) with Bromine Catalyzed by the Polyhalomethane*2AlBr3 Aprotic Organic Superacids under Mild Conditions

The polyhalomethane*2AlBr3 aprotic organic superacids were shown to effectively catalyze low-temperature ionic bromination of (cyclo)alkanes.Ethane readily reacts with Br2 at 55-65 deg C, affording mainly 1,2-dibromoethane.Propane, butane, and C5-C6 cycloalkanes react at -40 - -20 deg C, resulting in monobromides with high yields and good selectivity.