158635-38-2

Basic information

• Product Name: (S)-1-(2-chloro-phenyl)-propan-1-ol
• Synonyms: (S)-1-(2-chloro-phenyl)-propan-1-ol;(S)-1-(2-chlorophenyl)propanol
• CAS NO: 158635-38-2
• Molecular Formula: C₉H₁₁ClO
• Molecular Weight: 170.63604
• Mol File: 158635-38-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-1-(2-chloro-phenyl)-propan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-(2-chloro-phenyl)-propan-1-ol(158635-38-2)
• EPA Substance Registry System: (S)-1-(2-chloro-phenyl)-propan-1-ol(158635-38-2)

Safety Data

• Hazardous Substances Data: 158635-38-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-1-(2-chloro-phenyl)-propan-1-ol is used as a building block for the development of various pharmaceuticals. Its unique structure allows for the creation of new chemical entities that can be applied in the treatment and management of different health conditions.
Used in Agrochemical Industry:
In the agrochemical sector, (S)-1-(2-chloro-phenyl)-propan-1-ol serves as a crucial component in the synthesis of compounds used for pest control, crop protection, and other agricultural applications. Its incorporation into these products enhances their effectiveness and contributes to increased crop yields.
Used in Asymmetric Synthesis:
(S)-1-(2-chloro-phenyl)-propan-1-ol is utilized as a chiral auxiliary in asymmetric synthesis. This application is significant in the production of enantiomerically pure compounds, which are essential in various chemical and pharmaceutical processes due to their distinct biological activities and properties.
Used in Organic Chemistry Research:
As a versatile intermediate, (S)-1-(2-chloro-phenyl)-propan-1-ol is also employed in organic chemistry research. It aids in the exploration of new reaction pathways, the development of innovative synthetic methods, and the creation of novel chemical compounds with potential applications in various industries.

Upstream product

• 557-20-0 diethylzinc 
• 89-98-5 2-chloro-benzaldehyde 
• 97-93-8 triethylaluminum 
• 536-74-3 phenylacetylene 
• 6323-18-8 2-chloropropiophenone 
• 2386-64-3 ethylmagnesium chloride 
• 97-94-9 triethyl borane 

Relevant articles and documents

Deciphering the mechanism behind efficient enantioselective ethylation with thiazolidine-based amino alcohols

Taking advantage of the opposite chirality of two privileged starting materials, l-cysteine and d-penicillamine, a wide range of thiazolidine-based amino alcohols was synthesized. l-Cysteine derivatives were more efficient chiral inductors than the d-peni

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.

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.

Supramolecular Interlocked Biphenyl Ligands for Enantioselective Ti-Catalyzed Alkylation of Aromatic Aldehydes

The substitution of tropos 2,2′-biphenols with (S)-amino-acid-derived interaction sites in the 5,5′-position results in a spontaneous desymmetrization. This process is driven by well-defined intermolecular hydrogen bonding, which leads to diastereoselecti

Noscapine Derivatives as New Chiral Catalysts in Asymmetric Synthesis: Highly Enantioselective Addition of Diethylzinc to Aldehydes

Noscapine, a natural alkaloid, has never been used as a parent scaffold in chiral induction. The first examples of noscapinoid compounds as efficient catalysts in asymmetric synthesis are now reported. Three derivatives of noscapine were synthesized from its reaction with different Grignard reagents. Asymmetric addition of diethylzinc to aldehydes was performed in the presence of these catalysts in high yields and good to excellentees.

Chiral thiazolidines in the enantioselective ethylation of aldehydes: An experimental and computational study

A library of new chiral thiazolidines was prepared starting from L-cysteine and D-penicillamine in a simple, one-step procedure. 2-Arylthiazolidines were obtained, as diastereoisomeric mixtures, with good yields and in short reaction times, through a new and greener procedure, using microwave irradiation. Their use as chiral ligands in the enantioselective ethylation of aromatic aldehydes was studied and optimized, originating good to excellent conversions and ee up to 94% in 6 h. A series of heteroaromatic and aliphatic substrates were also enantioselectively ethylated with success, with ee up to 77%. The distinct opposite chirality in L-cysteine and D-penicillamine makes the use of these ligands an interesting approach for obtaining both the (S) and (R) enantiomers of the chiral alcohols, compounds with potential applications in the area of fine chemistry. NMR studies were carried out using a diastereoisomeric mixture of thiazolidines, allowing the identification of the most stable structure. Computational studies confirmed this result and also gave important insight into the species involved in the catalytic cycle of the enantioselective alkylation.

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.

Enantioselective alkylation of aromatic aldehydes with (+)-camphoric acid derived chiral 1,3-diamine ligands

A series of chiral 1,3-diamine ligands derived from (+)-camphoric acid were prepared from the reaction of 1,3-diamino-1,2,2-trimethylcyclopentane with aromatic aldehydes, followed by reduction of the corresponding diimines. These newly synthesized ligands

Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by Chiral O,N,O-tridentate Phenol Ligands Derived from Camphor

Chiral O,N,O-tridentate phenol ligands bearing a camphor backbone were found to be effective chiral catalysts for the enantioselective addition of diethylzinc to aromatic aldehydes, resulting in high enantioselectivities (80-95% ee) at room temperature.