131320-21-3

Basic information

• Product Name: (S)-1-(4-BROMOPHENYL)-1-PROPANOL
• Synonyms: (S)-1-(4-BROMOPHENYL)-1-PROPANOL;(S)-1-(4-broMophenyl)propanol;(S)-1-(4-broMophenyl)propan-1-ol
• CAS NO: 131320-21-3
• Molecular Formula: C₉H₁₁BrO
• Molecular Weight: 215.08704
• Mol File: 131320-21-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-1-(4-BROMOPHENYL)-1-PROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-(4-BROMOPHENYL)-1-PROPANOL(131320-21-3)
• EPA Substance Registry System: (S)-1-(4-BROMOPHENYL)-1-PROPANOL(131320-21-3)

Safety Data

• Hazardous Substances Data: 131320-21-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-1-(4-BROMOPHENYL)-1-PROPANOL is used as a building block for the production of pharmaceuticals due to its unique chiral structure. It plays a crucial role in the synthesis of various biologically active compounds, contributing to the development of new drugs and therapies.
Used in Agrochemical Industry:
In the agrochemical sector, (S)-1-(4-BROMOPHENYL)-1-PROPANOL is utilized as an intermediate in the synthesis of various agrochemicals. Its chiral nature allows for the creation of targeted and effective products for agricultural use.
Used in Organic Synthesis:
(S)-1-(4-BROMOPHENYL)-1-PROPANOL serves as an essential intermediate in organic synthesis, where it is employed to produce a wide range of fine chemicals. Its unique structure enables the creation of complex molecules with specific properties.
Used in Asymmetric Synthesis:
As a chiral auxiliary, (S)-1-(4-BROMOPHENYL)-1-PROPANOL is used in asymmetric synthesis to control the stereochemistry of reactions, leading to the production of enantiomerically pure compounds. This is particularly important in the pharmaceutical industry, where the desired biological activity is often associated with a specific enantiomer.
Used in Material Science:
(S)-1-(4-BROMOPHENYL)-1-PROPANOL has potential applications in the development of new materials, where its unique properties can be harnessed to create innovative and advanced materials with specific characteristics.
Used in Asymmetric Catalysis:
(S)-1-(4-BROMOPHENYL)-1-PROPANOL can also serve as a starting material for the preparation of chiral ligands used in asymmetric catalysis. The chiral ligands are essential in promoting enantioselective reactions, which are vital for producing optically active compounds with high purity and specificity.

Upstream product

• 557-20-0 diethylzinc 
• 1122-91-4 4-bromo-benzaldehyde 
• 108-05-4 vinyl acetate 
• 4489-22-9 (+/-)-1-(4-bromophenyl)propanol 
• 10342-83-3 4'-Bromopropiophenone 
• 97-93-8 triethylaluminum 
• 876-27-7 4-chlorophenyl acetate 
• 256378-84-4 acetic acid 1-(4-bromo-phenyl)-propyl ester 
• 760-19-0 Et₂AlBr 
• 100-58-3 phenylmagnesium bromide 
• 873-75-6 4-bromobenzenemethanol 
• 58824-56-9 1-(p-bromophenyl)prop-2-en-1-ol 
• 16184-89-7 4'-bromo-2,2,2-trifluoroacetophenone 
• 153457-05-7 1-(4-bromo-phenyl)-propanone oxime 

Relevant articles and documents

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.

Observation of hyperpositive non-linear effect in catalytic asymmetric organozinc additions to aldehydes

Asymmetric amplification is a phenomenon that is believed to play a key role in the emergence of homochirality in life. In asymmetric catalysis, theoretical and experimental models have been investigated to provide an understanding of how chiral amplification is possible, in particular based on non-linear effects. Interestingly, it has been proposed a quarter century ago that chiral catalysts, when not enantiopure might even be more enantioselective than their enantiopure counterparts. We show here that such hyperpositive non-linear effect in asymmetric catalysis is indeed possible. An in-depth study into the underlying mechanism was carried out, and the scheme we derive differs from the previous proposed models.

SECONDARY ARYL ALCOHOL AND METHOD OF SYNTHESIZING THEREOF

The present invention relates to secondary aryl alcohol and a method for synthesizing the same and, specifically, to synthesizing secondary aryl alcohol having high optical selectivity through a hydrosilylation reaction using ketone containing an aryl group. In the method for synthesizing secondary aryl alcohol according to an embodiment of the present invention, secondary aryl alcohol is synthesized by making ketone react with hydrosilane under a chiral boron Lewis acid catalyst.COPYRIGHT KIPO 2020

Isosterically designed chiral catalysts: Rationale, optimization and their application in enantioselective nucleophilic addition to aldehydes

Proline-based N,N′-dioxide ligands were designed on the basis of isosteric approach, and were successfully applied in enantioselective nucleophilic addition to aldehydes. In the presence of 10 mol% of chiral ligand 1b, enantioselective addition of diethylzinc to aldehydes provided the corresponding secondary alcohols in up to 90% isolated yield and up to 99% ee. Similarly, using 3e as chiral ligand, enantioselective arylation and alkynylation of aldehydes also proceeded readily, leading to the desired chiral alcohols in up to 92% isolated yield at 99% ee and 80% isolated yields and up to 84% ee, respectively. The current work would shed light on expanding the structure diversity in the design of chiral ligands and chiral catalysts.

Binaphthyl-based chiral ligands: Design, synthesis and evaluation of their performance in enantioselective addition of diethylzinc to aromatic aldehydes

The design strategy and the performance of binaphthyl-based chiral ligands were evaluated with computation and enantioselective addition of diethylzinc to aromatic aldehydes. Under optimized conditions, enantioselective addition of diethylzinc to aromatic aldehydes provided the desired optically active secondary alcohols in high isolated yields (up to 91%) and excellent enantiomeric excesses (up to 98% ee).

Linear β-amino alcohol catalyst anchored on functionalized magnetite nanoparticles for enantioselective addition of dialkylzinc to aromatic aldehydes

A linear β-amino alcohol ligand, previously found to be a very efficient catalyst for enantioselective addition of dialkylzinc to aromatic aldehydes, has been anchored on differently functionalized superparamagnetic core-shell magnetite-silica nanoparticles (1a and 1b). Its catalytic activity in the addition of dialkylzinc to aldehydes has been evaluated, leading to promising results, especially in the case of 1b for which the recovery by simple magnetic decantation and reuse was successfully verified. This journal is

Chiral zinc amidate catalyzed additions of diethylzinc to aldehydes

A series of bifunctional spiro ligands bearing “carboxamide–phosphine oxide” groups and ethylzinc carboxamidates from these ligands as catalysts for Et2Zn additions to aldehydes were reported. Excellent yields were obtained with moderate ee′s in Et2Zn additions to benzaldehyde derivatives, implying effectiveness of our newly designed catalytic structures as well as mediocre stereocontrol by these chiral ligands. Possible transition states were suggested based on the crystal structures of two ligands.

One-Pot Transformation of Ketoximes into Optically Active Alcohols and Amines by Sequential Action of Laccases and Ketoreductases or ω-Transaminases

An enzymatic one-pot process for asymmetric transformation of prochiral ketoximes into alcohols or amines was developed by sequential coupling of a laccase-catalyzed deoximation either with a ketone reduction (ketoreductase, KRED) or bioamination (ω-transaminase, ω-TA) in aqueous medium. An accurate selection of biocatalysts provided the corresponding products in excellent enantiomeric excesses and overall conversions ranging from 83 to >99 % for alcohols and 70 to >99 % for amines. Likewise, the employment of exclusively 1 % (w/w) of Cremophor, a polyethoxylated castor oil, as co-solvent enabled to reach concentrations up to 100 mM in the chiral alcohols cascade.

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.

Chiral 2-(2-hydroxyaryl)alcohols (HAROLs) with a 1,4-diol scaffold as a new family of ligands and organocatalysts

Efficient and modular syntheses of chiral 2-(2-hydroxyaryl)alcohols (HAROLs), novel 1,4-diols carrying one phenolic and one alcohol hydroxyl group, have been developed which led to generation of a small library of structurally diverse HAROLs in enantiomerically pure form. Of the different HAROLs examined, a HAROL based on the indan backbone exhibited the highest activity and enantioselectivity in the 1,2-addition of certain organometallic compounds to aldehydes in the presence of Ti(OiPr)4 (up to 97% y, 88% ee) and performed as a hydrogen-bond donor organocatalyst in the Morita-Baylis-Hillman reaction, promoted by trialkylphosphines.