224622-38-2

Usage

Uses

Used in Pharmaceutical Industry:
(S)-α-(3'-bromophenyl)propanol is used as a synthetic intermediate for the production of various pharmaceuticals. Its unique chiral structure allows for the creation of enantiomer-specific drugs, which can have different effects on the body and are crucial in developing targeted treatments for specific medical conditions.
Used in Organic Compound Synthesis:
In the field of organic chemistry, (S)-α-(3'-bromophenyl)propanol serves as a key building block for synthesizing a wide range of organic compounds. Its versatility in reacting with other molecules makes it an essential component in the development of new materials and chemicals with diverse applications.

Upstream product

• 3132-99-8 m-bromobenzoic aldehyde 
• 557-20-0 diethylzinc 
• 108-05-4 vinyl acetate 
• 74157-47-4 (+/-)-1-(3-bromophenyl)propanol 
• 1019940-69-2 C₁₁H₁₃BrO₂ 
• 19829-31-3 1-(3-bromophenyl)-1-propanone 

Downstream Products

• 594854-57-6 (R)-3-(tert-Butyl-dimethyl-silanyloxy)-1-[3-((S)-1-hydroxy-propyl)-phenyl]-2-methyl-propan-1-one 
• 613-87-6 (S)-1-phenyl-1-propanol 
• 594855-07-9 (2R,4S)-4-((Z)-(S)-5-{3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-phenyl}-4-methyl-2-methylsulfanyl-pent-2-enyl)-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester 
• 594855-17-1 (2R,4S)-4-((Z)-(S)-5-{3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-phenyl}-2-chloro-4-methyl-pent-2-enyl)-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester 
• 594855-10-4 C₃₁H₃₈O₅S 
• 594855-20-6 C₃₀H₃₅ClO₅ 
• 594855-09-1 (2R,4S)-4-{(Z)-(S)-5-[3-((S)-1-Acetoxy-propyl)-phenyl]-4-methyl-2-methylsulfanyl-pent-2-enyl}-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester 
• 594855-19-3 (2R,4S)-4-{(Z)-(S)-5-[3-((S)-1-Acetoxy-propyl)-phenyl]-2-chloro-4-methyl-pent-2-enyl}-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester 
• 594855-22-8 C₃₁H₃₇ClO₅ 
• 594855-21-7 C₃₁H₃₇ClO₅ 
• 594855-18-2 (2R,4S)-4-{(Z)-(S)-2-Chloro-5-[3-((S)-1-hydroxy-propyl)-phenyl]-4-methyl-pent-2-enyl}-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester 
• 594855-08-0 (2R,4S)-4-{(Z)-(S)-5-[3-((S)-1-Hydroxy-propyl)-phenyl]-4-methyl-2-methylsulfanyl-pent-2-enyl}-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester 
• 594854-60-1 dithiocarbonic acid O-(3-(tert-butyl-dimethyl-silanyloxy)-1-{3-[1-(tert-butyl-dimethyl-silanyloxy)-propyl]-phenyl}-2-methyl-propyl) ester S-methyl ester 
• 594854-59-8 3-(tert-butyl-dimethyl-silanyloxy)-1-{3-[1-(tert-butyl-dimethyl-silanyloxy)-propyl]-phenyl}-2-methyl-propan-1-ol 

Relevant academic research and scientific papers

Abiotic reduction of ketones with silanes catalysed by carbonic anhydrase through an enzymatic zinc hydride

Enzymatic reactions through mononuclear metal hydrides are unknown in nature, despite the prevalence of such intermediates in the reactions of synthetic transition-metal catalysts. If metalloenzymes could react through abiotic intermediates like these, then the scope of enzyme-catalysed reactions would expand. Here we show that zinc-containing carbonic anhydrase enzymes catalyse hydride transfers from silanes to ketones with high enantioselectivity. We report mechanistic data providing strong evidence that the process involves a mononuclear zinc hydride. This work shows that abiotic silanes can act as reducing equivalents in an enzyme-catalysed process and that monomeric hydrides of electropositive metals, which are typically unstable in protic environments, can be catalytic intermediates in enzymatic processes. Overall, this work bridges a gap between the types of transformation in molecular catalysis and biocatalysis. [Figure not available: see fulltext.]

Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Using Novel Thiophene-Based Chiral Ligands

Abstract: Chiral norephedrine-derived β-amino alcohols with a thiophene moiety were synthesized from thiophene carbaldehydes (methyl- or ethyl-substituted) and chiral amino alcohols, such as both enantiomers of norephedrine and 2-aminopropanol. The synthesized ligands were applied to the catalytic asymmetric addition of diethylzinc to aldehydes to obtain optically active alcohols with a high conversion (92%) and excellent enantioselectivities (ee up to 99%). The highest enantioselectivity (ee 99%) was obtained with p-trifluorobenzaldehyde as the substrate containing the strongly electron-acceptor CF3 group.

Chiral P,N-ligands for the highly enantioselective addition of diethylzinc to aromatic aldehydes

A new sterically hindered chiral P,N-ligand was synthesized and successfully applied to copper catalyzed asymmetric addition of diethylzinc to aromatic aldehydes. Various aromatic aldehydes can react smoothly to give the corresponding addition products with good to excellent enantioselectivities, which provides a readily accessible method for the preparation of chiral secondary alcohols.

New chiral amino alcohol ligands for catalytic enantioselective addition of diethylzincs to aldehydes

A study aimed at the synthesis and structure optimization of new, efficient, optically active β-amino alcohol ligands with a structure suitable for immobilization on magnetite nanoparticles has been carried out. The optimized homogeneous amino alcohol catalysts 13a and 13b, the chirality of which arises from the Sharpless epoxidation of suitable allyl alcohols, were tested by employing the well-established enantioselective amino alcohol-promoted addition of diethylzinc to benzaldehyde, giving the corresponding benzyl alcohol with nearly quantitative yield and ee = 95%. Then, their broad applicability as chiral catalysts was evaluated by carrying out the same reaction on a family of aldehydes, including variously substituted aromatic ones as well as an aliphatic analogue. The results have confirmed the validity of the fine-tuning process performed on ligands 13a and 13b. In fact, both exhibited excellent catalytic activity as demonstrated by the chemical yields and ee obtained from all the tested aldehydes, almost independent of the position and type of substitution in the aromatic ring.

Development of Axially Chiral Cyclo-Biaryldiol Ligands with Adjustable Dihedral Angles

A new type of axially chiral cyclo-[1,1′-biphenyl]-2,2′-diol (CYCNOL) ligands with adjustable dihedral angles have been developed by varying the bridge chain length. Eight-, nine- and ten-membered cyclo-ligands were prepared and evaluated by using two representative examples: enantioselective additions of diethylzinc to aldehydes and organometallic reagents to enones. The results revealed that the fine regulation of dihedral angles through variation of the bridge chain length was effective in the asymmetric synthesis.

Synthesis of quinazolinone-based aziridine diols as chiral ligands: Dual stereoselectivity in the asymmetric ethylation of aryl aldehydes Dedicated to Professor Dr. Metin Balci on the occasion of his retirement

A new class of quinazoline-based enantiomerically pure aziridine diols 4a-d were prepared from the aziridination of mesityl oxide 3 with in situ generated 3-acetoxyaminoquinazolinone (S)-2b followed by NaBH4 reduction. Aziridine diols 4a-d were purified by means of column chromatography on silica gel and their stereochemistries were assigned by X-ray crystallography and NMR analysis. These aziridine diols 4 were evaluated as chiral ligands in the asymmetric addition of diethylzinc to aryl aldehydes, and ligand (S,R,R)-4a yielded (R)-1-phenylpropanol derivatives with up to 92% ee, while the diastereomer (S,S,R)-4c gave the opposite enantiomers (S)-1-phenylpropanol derivatives with up to 86% ee. The results demonstrate that switching the configuration of the aziridine alcohol moiety in ligand gives a remarkable reversal of enantioselectivity in the asymmetric addition of diethylzinc to aryl aldehydes.

Vasicine as tridentate ligand for enantioselective addition of diethylzinc to aldehydes

The first report of natural l-vasicine as tridentate chiral ligand for the enantioselective addition of diethylzinc to a variety of aliphatic and aromatic aldehydes is described. The ligand generates R-isomer of the secondary alcohols upto 98% ee. The qui

Thermophysical properties of imidazolium-functionalized binols and their application in asymmetric catalysis

We report here the thermophysical properties of a new family of imidazolium-functionalized binaphthols. These properties are influenced by the position of the imidazolium moieties on the binaphthol skeleton, the counteranions, and the length of the carbon chain on the imidazolium moieties. The ionic character of these molecules was also exploited to develop ligands for the catalytic aldehyde ethylation reaction in ionic liquid media. We were able to easily recover both the ionic ligands and the ionic liquid solvent, and the reaction afforded good to excellent yields, with average selectivity.

2-Pyridylsulfinamides as effective catalysts in the asymmetric alkylation of aldehydes with diethylzinc Dedicated to Dr. N.N. Joshi, National Chemical Laboratory, Pune, India

Chiral 2-pyridylsulfinamides were shown to be effective catalysts in the alkylation of aryl and alkyl aldehydes with diethylzinc providing the corresponding alcohols in excellent enantioselectivity. Sulfinamide catalysts possessing solitary chirality at the sulfur center produced the product phenethyl alcohol in good enantioselectivity. Diastereomeric sulfinamides possessing chirality at the carbon-bearing nitrogen and at the sulfur of the sulfinamide increased the enantioselectivity of the product alcohols up to >99%. However, there is no effect of the match-mismatch pair of sulfinamide diastereomers on the outcome of the chiral induction of the product phenethyl alcohols. It was conclusively proved that chirality at the sulfur center is mandatory for obtaining good enantioselectivity in the reaction.