126624-06-4

Basic information

• Product Name: (R)-(+)-1-(2'-Methylphenyl)-1-propanol
• Synonyms: (R)-(+)-1-(2'-Methylphenyl)-1-propanol;(R)-1-(2-tolyphenyl)-1-propanol
• CAS NO: 126624-06-4
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.21756
• Mol File: 126624-06-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-(+)-1-(2'-Methylphenyl)-1-propanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1-(2'-Methylphenyl)-1-propanol(126624-06-4)
• EPA Substance Registry System: (R)-(+)-1-(2'-Methylphenyl)-1-propanol(126624-06-4)

Safety Data

• Hazardous Substances Data: 126624-06-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agricultural Chemical Synthesis:
(R)-(+)-1-(2'-Methylphenyl)-1-propanol is used as a chiral auxiliary in the synthesis of various pharmaceuticals and agricultural chemicals. Its unique chirality allows for the creation of specific enantiomers, which can have different biological activities and are crucial in the development of effective and safe drugs.
Used in Fragrance Industry:
(R)-(+)-1-(2'-Methylphenyl)-1-propanol is used as a fragrance ingredient due to its pleasant, floral aroma. It is often included in perfumes and other scented products, adding a desirable scent and enhancing the overall fragrance experience.
Used in Flavoring Industry:
In addition to its use in fragrances, (R)-(+)-1-(2'-Methylphenyl)-1-propanol is also used as a flavoring agent in the food products industry. Its floral aroma can be used to add a unique and appealing taste to various food items.
Used in Development of New Materials:
(R)-(+)-1-(2'-Methylphenyl)-1-propanol has potential applications in the development of new materials due to its unique chirality and reactivity. It can be used as a building block or a starting material for the synthesis of novel compounds with specific properties, which can be applied in various fields, such as electronics, plastics, and coatings.
Used in Organic Synthetic Chemistry:
(R)-(+)-1-(2'-Methylphenyl)-1-propanol is also utilized in organic synthetic chemistry as a versatile reagent or intermediate for the synthesis of complex organic molecules. Its unique structure and reactivity make it a valuable tool for chemists in designing and creating new compounds with specific functions and applications.

Upstream product

• 557-20-0 diethylzinc 
• 529-20-4 2-methylphenyl aldehyde 
• 2040-14-4 2-methylpropiophenone 
• 925-90-6 ethylmagnesium bromide 
• 89-95-2 2-methyl-benzyl alcohol 
• 117-34-0 2,2-diphenylacetic acid 
• 61017-92-3 1-(2-methylphenyl)-1-propanol 
• 39627-62-8 1-(o-tolyl)-2-propen-1-ol 

Relevant articles and documents

2,2′-Bipyridine-α,α′-trifluoromethyl-diol ligand: Synthesis and application in the asymmetric Et2Zn alkylation of aldehydes

A chiral 2,2′-bipyridine ligand (1) bearing α,α′-trifluoromethyl-alcohols at 6,6′-positions was designed in five steps affording either the R,R or S,S enantiomer with excellent stereoselectivities, i.e. 97% de, >99% ee and >99.5% de, >99.5% ee, respectively. The key step for reaching high levels of stereoselectivity was demonstrated to be the resolution of the α-CF3-alcohol using (S)-ibuprofen as the resolving agent. An initial application for the 2,2′-bipyridine-α,α′-CF3-diol ligand was highlighted in the ZnII-catalyzed asymmetric ethylation reaction of aromatic, heteroaromatic, and aliphatic aldehydes. Synergistic electron deficiency and steric hindrance properties of the newly developed ligand afforded the corresponding alcohols in good to excellent yields (up to 99%) and enantioselectivities (up to 95% ee). As observed from single crystal diffraction analysis, the complexation of the 2,2′-bipyridine-α,α′-CF3-diol ligand generates an unusual hexacoordinated ZnII.

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

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).

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.

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.

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

Abstract: Chiral oxazoline ligands containing an aromatic ring were prepared fromnorephedrine and pyrrole-2-carbonitrile or 2-hydroxybenzoyl chloride. Thesynthesized ligands were used in the copper-catalyzed asymmetric addition ofdiethylzinc to aromatic aldehydes to provide optically active 1-arylpropan-1-olswith high conversion (92%) and enantioselectivity (up to 99% 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

Enantioselective addition of diethylzinc to aldehydes catalyzed by 5-cis-substituted proline derivatives

5-Cis-substituted prolinols, prolinamines, and prolinamine sulfonamides proved to be efficient ligands for the enantioselective addition of diethylzinc to aldehydes, providing up to 99% ee. The sense of asymmetric induction can be controlled by the nature

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.

Chiral Lithium Amido Zincates for Enantioselective 1,2-Additions: Auto-assembling Reagents Involving a Fully Recyclable Ligand

A methodology consisting in carrying out enantioselective nucleophilic 1,2-additions (ee values up to 97 %) from cheap, easily accessible, and never described before, chiral lithium amido zincates is presented. These multicomponent reactants auto-assemble when mixing, in a 1:1 ratio, a homoleptic diorganozinc (R2Zn) with a chiral lithium amide (CLA). The latter, obtained after a single reductive amination, plays the role of the chiral inductor and is fully recoverable thanks to a simple acid–base wash, allowing being recycled and re-use without loss of stereochemical information.