5978-55-2

Usage

Uses

Used in Organic Synthesis:
[R,(-)]-2-Bromooctane is used as a reagent in organic synthesis for the preparation of various organic compounds. Its unique structure allows for the formation of new chemical bonds and the synthesis of complex molecules.
Used in Pharmaceutical and Agrochemical Industries:
[R,(-)]-2-Bromooctane is used as a starting material in the synthesis of pharmaceuticals and agrochemicals. Its versatility and reactivity make it a valuable component in the development of new drugs and agricultural chemicals.
Used in Research Studies:
[R,(-)]-2-Bromooctane is used as a chiral auxiliary in research studies to develop new synthetic methodologies and investigate the stereochemistry of organic reactions. Its chiral nature provides a unique platform for understanding the behavior of chiral compounds in chemical reactions.
However, it is crucial to handle [R,(-)]-2-Bromooctane with care due to its toxic nature and potential to cause irritation to the skin, eyes, and respiratory system. Proper safety measures should be taken to minimize exposure and ensure the safe use of this chemical compound.

Upstream product

• 60-29-7 diethyl ether 
• 34817-25-9 (S)-1-methylheptyl tosylate 
• 506-96-7 Acetyl bromide 
• 7598-65-4 phosphorous acid tris-((S)-1-methyl-heptyl ester) 
• 6169-06-8 (S)-2-Octanol 
• 103514-67-6 C₁₄H₃₅N₃PS⁽¹⁺⁾ 
• 75808-97-8 (S)-(+)-2-octyl phenyl selenide 
• 10035-10-6 hydrogen bromide 
• 7789-60-8 phosphorus tribromide 
• 7789-69-7 phosphorus pentabromide 
• 776-74-9 Bromodiphenylmethane 
• 1809-04-7 (S)-(+)-2-iodooctane 
• 7726-95-6 bromine 
• 7598-65-4 (+)(S:S:S)-tris-(1-methyl-heptyl)-phosphite 

Downstream Products

• 6169-06-8 (S)-2-Octanol 
• 36978-30-0 (S)-2-ethoxy-octane 
• 13151-29-6 (4S)-4-methyldec-1-ene 
• 198956-40-0 (2S)-2-Benzyloctane 
• 111-65-9 octane 
• 5911-04-6 3-methyl-nonane 
• 111-66-0 oct-1-ene 
• 2801-86-7 7,8-Dimethyltetradecane 
• 37152-54-8 {[(1S)-1-methylheptyl]oxy}cyclohexane 
• 122289-47-8 methyl 3-bromo-4-<<(S)-1-methylheptyl>oxy>benzoate 
• 111265-18-0 (S)-(+)-2-octyl phenyl sulfide 
• 76003-59-3 (S_c)-methyl 2-(2-octylthio)benzoate 
• 116836-12-5 (S)-2-nitro-octane 
• 777-22-0 2-phenyloctane 

Relevant academic research and scientific papers

One-Pot Deoxygenation and Substitution of Alcohols Mediated by Sulfuryl Fluoride

Sulfuryl fluoride is a valuable reagent for the one-pot activation and derivatization of aliphatic alcohols, but the highly reactive alkyl fluorosulfate intermediates limit both the types of reactions that can be accessed as well as the scope. Herein, we report the SO2F2-mediated alcohol substitution and deoxygenation method that relies on the conversion of fluorosulfates to alkyl halide intermediates. This strategy allows the expansion of SO2F2-mediated one-pot processes to include radical reactions, where the alkyl halides can also be exploited in the one-pot deoxygenation of primary alcohols under mild conditions (52-95% yield). This strategy can also enhance the scope of substitutions to nucleophiles that are previously incompatible with one-pot SO2F2-mediated alcohol activation and enables substitution of primary and secondary alcohols in 54-95% yield. Chiral secondary alcohols undergo a highly stereospecific (90-98% ee) double nucleophilic displacement with an overall retention of configuration.

DESIGN AND REACTIVITY OF ORGANIC FUNCTIONAL GROUPS - 2-PYRIDYLSULFONATES AS NUCLEOFUGAL ESTERS: REMARKABLY MILD TRANSFORMATIONS INTO HALIDES AND OLEFINS

The novel 2-pyridylsulfonate esters are excellent leaving groups for the preparation of bromides and olefins under very mild reaction conditions.Displacements occur with inversion of configuration.

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.

STEREOSPECIFIC DISPLACEMENT OF SULFUR FROM CHIRAL CENTERS. ACTIVATION VIA THIAPHOSPHONIUM SALTS.

The first general method for direct displacement of sulfur from chiral carbon centers has been developed.Chiral mercaptans are readily converted to the corresponding thiaphosphonium salts by treatment with t-butyl hypochlorite and hexamethylphosphorous triamide.Metathesis with ammonium hexafluorophosphate provides stable, isolable, crystalline salts which undergo clean nucleophilic diplacement with a variety of heteroatom and carbon based nucleophiles, affording products in which the stereochemistry has been inverted.

New Stereoselective Routes from Alcohols to Secondary Alkyl Bromides with Retention of Configuration

Secondary alcohols can be converted into the corresponding bromides with high stereoselective retention of configuration; this two-step process proceeds by a double inversion involving the intermediate selenides.