213267-92-6

Basic information

• Product Name: (1S)-1-(3-Methylphenyl)-1-propanol
• Synonyms: (1S)-1-(3-Methylphenyl)-1-propanol;(S)-1-(3-tolyphenyl)-1-propanol
• CAS NO: 213267-92-6
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.21756
• Mol File: 213267-92-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1S)-1-(3-Methylphenyl)-1-propanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-1-(3-Methylphenyl)-1-propanol(213267-92-6)
• EPA Substance Registry System: (1S)-1-(3-Methylphenyl)-1-propanol(213267-92-6)

Safety Data

• Hazardous Substances Data: 213267-92-6(Hazardous Substances Data)

Usage

Uses

Used in Fragrance and Perfume Industry:
(1S)-1-(3-Methylphenyl)-1-propanol is used as a fragrance ingredient for its floral, fruity scent, adding a pleasant aroma to perfumes and other scented products.
Used in Flavoring Industry:
(1S)-1-(3-Methylphenyl)-1-propanol is used as a flavoring ingredient, enhancing the taste and aroma of various food and beverage products.
Used in Cosmetic and Personal Care Products:
(1S)-1-(3-Methylphenyl)-1-propanol is used in the manufacturing of cosmetic and personal care products, contributing to their scent and potentially providing some skin conditioning properties.
However, it is important to note that (1S)-1-(3-Methylphenyl)-1-propanol is known for its potential skin irritation and sensitization properties. Therefore, it should be handled with care in industrial and laboratory settings to minimize any adverse effects on users and workers.

Upstream product

• 557-20-0 diethylzinc 
• 620-23-5 m-tolyl aldehyde 
• 587-03-1 3-methylbenzyl alcohol 
• 17271-70-4 β-methyl-3-methylstyrene 
• 536-74-3 phenylacetylene 
• 403501-31-5 (1R,2S)-1-(3-methylphenyl)-1-propene oxide 

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.

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.

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.

New C2-symmetric six-membered carbene ligands for asymmetric diethylzinc addition of arylaldehydes

A series of new six-membered NHC precursors were prepared by simply esterification of their parent compounds. Their applicability in asymmetric diethylzinc addition of arylaldehydes has been demonstrated and the corresponding secondary alcohol was obtained with good yields and moderate enantioselectivities. (Figure pressented)

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.

Nickel-Catalyzed Enantioconvergent Borylation of Racemic Secondary Benzylic Electrophiles

Nickel-catalyzed cross-coupling has emerged as the most versatile approach to date for achieving enantioconvergent carbon–carbon bond formation using racemic alkyl halides as electrophiles. In contrast, there have not yet been reports of the application of chiral nickel catalysts to the corresponding reactions with heteroatom nucleophiles to produce carbon–heteroatom bonds with good enantioselectivity. Herein, we establish that a chiral nickel/pybox catalyst can borylate racemic secondary benzylic chlorides to provide enantioenriched benzylic boronic esters, a highly useful family of compounds in organic synthesis. The method displays good functional group compatibility (e.g., being unimpeded by the presence of an indole, a ketone, a tertiary amine, or an unactivated alkyl bromide), and both of the catalyst components (NiCl2?glyme and the pybox ligand) are commercially available.

Stereoselective Synthesis and Modelling-Driven Optimisation of Carane-Based Aminodiols and 1,3-Oxazines as Catalysts for the Enantioselective Addition of Diethylzinc to Benzaldehyde

The reductive amination of (-)-2-carene-3-aldehyde, prepared in two steps from (-)-perillaldehyde, furnished 2-carene-based allylamines. tert-Butyloxycarbonyl (Boc) or carbobenzyloxy (Cbz) protection of the resulting amines, followed by stereoselective dihydroxylation in highly stereospecific reactions with OsO4 and subsequent deprotection, resulted in N-benzylaminodiols, which were transformed to primary and tertiary aminodiols. The reactions of the N-benzyl- and N-(1-phenylethyl)-substituted derivatives with formaldehyde led to highly regioselective ring closure, resulting in carane-fused 1,3-oxazines. The aminodiols and their 1,3-oxazine derivatives were applied as chiral catalysts in the enantioselective addition of diethylzinc to aldehydes. The best (R) enantioselectivity was observed in the case of the N-((R)-1-phenylethyl)-substituted aminodiol, whereas the opposite chiral direction was preferred when the 1,3-oxazines were applied. Through the use of molecular modelling at an ab initio level, this phenomenon was interpreted in terms of competing reaction pathways. Molecular modelling at the RHF/LANL2DZ level of theory was successfully applied for a mechanism-based interpretation of the stereochemical outcome of the reactions leading to the development of further 1,3-oxazine-based ligands, which display excellent (S) enantioselectivity (95 and 98 % ee) in the examined transformation.

Mechanistic implications of the enantioselective addition of alkylzinc reagents to aldehydes catalyzed by nickel complexes with α-amino amide ligands

The enantioselective alkylation of aldehydes catalysed by nickel(ii)-complexes derived from α-amino amides was studied by means of density functional theory (DFT) and ONIOM (B3LYP:UFF) calculations. A mechanism was proposed in order to investigate the origin of enantioselectivity. The chirality-determining step for the alkylation was the formation of the intermediate complexes with the involvement of a 5/4/4-fused tricyclic transition state. The predominant products predicted theoretically were of (S)-configuration, in good agreement with experimental observations. The scope of the reaction was examined and high yields and enantioselectivities were observed for the enantioselective addition of Et2Zn and Me2Zn to aromatic and aliphatic aldehydes.