5787-33-7

Usage

Uses

Used in Pharmaceutical Industry:
[R,(-)]-2-Bromobutane is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to facilitate the formation of desired molecular structures through organic reactions.
Used in Agrochemical Industry:
[R,(-)]-2-Bromobutane is used as a precursor in the production of agrochemicals, contributing to the development of effective compounds for agricultural applications.
Used in Flavor Industry:
[R,(-)]-2-Bromobutane is used as a building block in the creation of flavors, leveraging its reactivity to produce specific aromatic compounds.
Used in Organic Synthesis:
[R,(-)]-2-Bromobutane is used as a versatile solvent and intermediate in organic synthesis, enabling the production of a wide range of organic compounds for various applications.
Used in Organic Chemistry Research:
[R,(-)]-2-Bromobutane is used as a reagent in nucleophilic substitution reactions, aiding researchers in understanding and advancing the field of organic chemistry.

Upstream product

• 14898-79-4 (2R)-butan-2-ol 
• 4221-99-2 (S)-2-butanol 
• 62736-86-1 (R)-(-)-triisopropyl-sec-butyltin 
• 106251-39-2 (R)-(-)-diisopropylneopentyl-sec-butyltin 
• 78-76-2 s-butyl bromide 
• 357-57-3 brucine 

Downstream Products

• 35778-39-3 3-methyl-4-nonanone 
• 22156-93-0 (R)-2-ethylsulfanyl-butane 
• 16725-75-0 -(-)-1-methylpropyl phenyl ketone 
• 60053-31-8 2-bromo-2-chloro-butane 
• 19246-45-8 threo-2-bromo-3-chlorobutane 
• 49623-68-9 (R)-1-bromo-2-chloro-butane 
• 49623-65-6 (2S)-erythro-2-bromo-3-chloro-butane 
• 49623-67-8 (S)-3-bromo-1-chloro-butane 
• 119785-70-5 (S)-(+)-s-butyl phenyl sulfide 
• 77080-43-4 trans-15,16-dimethyl-1,4,8,11-ethanediylidene<14>annulene 
• 139942-99-7 trans-15-sec-butyl-16-methyl-1,4,8,11-ethanediylidene<14>annulene 
• 122876-32-8 trans-15,16-di-sec-butyl-1,4,8,11-ethanediylidene<14>annulene 
• 139914-65-1 C₂₄H₂₈ 
• 81928-51-0 (C₆H₅)3SnCH(CH₃)C₂H₅ 

Relevant academic research and scientific papers

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.

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.

Asymmetric Alkylation of β-Keto Esters with Optically Active Sulfonium Salts

Alkylation of the cyclic β-keto ester2-(methoxycarbonyl)-1-indanone (2) with racemic alkylsulfonium salts 1a-h gave 2-alkylindanones 3 and 4 in 60-96percent yields.The relative reactivities of the alkyl substituents of aryldialkylsulfonium salts 1e and 1f were quite different from those in SN2 alkylations.Asymmetric induction occured upon alkylation of 2 with optically active sulfonium salts. (R)-2-Ethyl-2-(methoxycarbonyl)cyclohexanone (11) was obtained in up to 16percent ee by alkylation of the enolate ion of 2-(methoxycarbonyl)cyclohexanone (9) with optically active (R)-(+)-(p-chlorophenyl)ethylmethylsulfonium d-10-camphorsulfonate (1k).Alkylation of the enolate ion of 2 with sulfonium salts containing optically active alkyl groups afforded C-alkylated products with inversion of configuration at the asymmetric alkyl carbon atom.These alkylations appear to proceed via an S-O sulfurane intermediate or a tight ion pair with subsequent stereoselective alkyl migration to the enolate.

Stereochemistries and mechanisms of reactions of electrophiles with organotin compounds

The effect of solvent and electrophile on halodemetalation reactions of carbon-tin bonds has been investigated. Both stereochemical results and 119Sn NMR have been used as mechanistic probes. The effect of solvent is extreme; reactions performed in polar solvents such as acetonitrile and dimethylformamide yield cleavage products with predominantly inversion of configuration, whereas nonpolar solvents yield products with predominantly retention. Polar-aprotic solvents appear to be highly efficient in promoting inversion stereochemistry. Polar-protic solvents are not as efficient. This is explained in terms of some very specific solvation phenomena. Also, 119Sn NMR studies of several trialkyltin halides in various solvents show that these specific solvation phenomena can be qualitatively assessed. The nature of the electrophile also plays an important role in eventual stereochemistry; Br2, I2, ICl, and IBr are compared and discussed.