2406-22-6

Basic information

• Product Name: (S)-2-Phenylpropane-1,2-diol
• Synonyms: (2S)-2-Phenyl-1,2-propanediol;(S)-2-Phenylpropane-1,2-diol;[S,(+)]-2-Phenyl-1,2-propanediol
• CAS NO: 2406-22-6
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19
• Mol File: 2406-22-6.mol
• Article Data: 105

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-2-Phenylpropane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-Phenylpropane-1,2-diol(2406-22-6)
• EPA Substance Registry System: (S)-2-Phenylpropane-1,2-diol(2406-22-6)

Safety Data

• Hazardous Substances Data: 2406-22-6(Hazardous Substances Data)

Usage

General Description

(S)-2-Phenylpropane-1,2-diol, also known as (S)-1,2-propanediol, is a chemical compound with the molecular formula C9H12O2. It is a colorless liquid with a floral, rose-like odor, commonly used in the production of perfumes and as a flavoring agent in food and beverages. It is also used in the pharmaceutical industry as a chiral building block for the synthesis of various compounds. Additionally, (S)-2-Phenylpropane-1,2-diol is known for its natural occurrence in certain plants and their essential oils, and is often used in the formulation of natural and organic skincare and beauty products due to its hydrating and soothing properties. (S)-2-Phenylpropane-1,2-diol has also been studied for its potential anti-inflammatory and antioxidant properties, making it a versatile and valuable ingredient in various industries.

Upstream product

• 98-83-9 isopropenylbenzene 
• 266694-57-9 Phenyl-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-methanone 
• 2085-88-3 2-methyl-2-phenyloxirane 
• 4217-66-7 1,2-dihydroxy-2-phenylpropane 
• 590-86-3 isovaleraldehyde 
• 75-07-0 acetaldehyde 
• 110-62-3 pentanal 
• 78-84-2 isobutyraldehyde 
• 2987-16-8 3,3-dimethylbutyrylaldehyde 
• 88292-45-9 (1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (R)-2-hydroxy-2-phenylpropanoate 
• 173031-59-9 Methyl 2-phenyl-2-(2,4,6-triisopropylbenzyloxy)propionate 
• 108-22-5 Isopropenyl acetate 
• 682352-12-1 (1S,2R,3S,5R,1'S,2'R)-6,6-dimethyl-3-(1'-ethoxy-2'-phenyl-2'-hydroxy-1'-propylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 
• 682352-19-8 (1S,2R,3S,5R,1'R,2'S)-6,6-dimethyl-3-(1'-ethoxy-2'-phenyl-2'-hydroxy-1'-propylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 

Downstream Products

• 135042-87-4 (R)-(+)-2-cyclohexylpropane-1,2-diol 
• 2453-58-9 (S)-1-tosyloxy-2-phenylpropan-2-ol 
• 17643-24-2 (R)-1-amino-2-phenylpropan-2-ol 
• 4361-50-6 (R)-2-hydroxy-2-phenylpropanaldehyde 
• 7782-26-5 (R)-2-Phenylpropionic acid 
• 7782-24-3 (S)-2-Phenylpropionic acid 
• 2085-88-3 (R)-2-methyl-2-phenyloxirane 
• 53777-08-5 (S)-2-phenyl-butan-2-ol 
• 2404-43-5 (2S)-2-methyl-2-phenyloxirane 
• 627076-70-4 (R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate 
• 37778-99-7 (S)-2-phenyl-1-propanol 
• 1123-85-9 (+)-(R)-2-phenylpropanol 

Relevant articles and documents

Synthesis and stereoselective evaluation of a (1R)-(–)-myrtenal-derived pseudo C2-symmetric dodecaheterocycle as a potential heterofunctional chiral auxiliary

The synthesis and diastereoselective performance of the pseudo C2-symmetric dodecaheterocycle 3 in nucleophilic and electrophilic reactions are reported. Compound 3 proved to be a highly diastereoselective template to generate a pair of enantiomeric moieties within its structure in a programmed manner. Hence, this study describes the synthesis of a novel potential heterobifunctional chiral auxiliary.

Chiral-auxiliary-controlled diastereoselectivity in the epoxidation of enecarbamates with DMD and mCPBA

(Matrix presented) Chiral oxazolidinone-substituted enecarbamates 1 are epoxidized in a diastereoselectivity up to 93:7 for both DMD and mCPBA. The diastereofacial differentiation depends on the steric interaction between the R1 substituent on the oxazolidinone ring and the incoming electrophile. The stereochemical course of epoxidation was assessed by chemical correlation with the known optically active diols.

An improved version of the Sharpless asymmetric dihydroxylation

The osmium catalyzed asymmetric dihydroxylation of olefins (Sharpless AD) was studied under controlled pH conditions. It was found that providing a constant pH value of 12.0 leads to improved reaction rates for internal olefins. Hydrolysis aids such as methanesulfonamide can be omitted. For terminal olefins, working at a constant pH of 10.0 at room temperature leads to higher enantioselectivities compared to AD reactions without pH control. (C) 2000 Elsevier Science Ltd.

Absolute stereochemical determination of 1,2-diols via complexation with dinaphthyl borinic acid

Rapid derivatization of chiral 1,2-diols with dinaphthyl borinic acid (DBA) leads to a cyclic boronate, enabling the absolute stereochemical prediction via exciton-coupled circular dichroic (ECCD) of the naphthyl groups. Aryl- and alkyl-substituted 1,2-diols derivatized with DBA yield a predictable ECCD, which is also in agreement with theoretical predictions derived from computationally minimized structures.

Syn-dihydroxylation of alkenes using a sterically demanding cyclic diacyl peroxide

The syn-dihydroxylation of alkenes is a highly valuable reaction in organic synthesis. Cyclic acyl peroxides (CAPs) have emerged recently as promising candidates to replace the commonly employed toxic metals for this purpose. Here, we demonstrate that the structurally demanding cyclic peroxide spiro[bicyclo[2.2.1]heptane-2,4′-[1,2]dioxolane]-3′,5′-dione (P4) can be effectively used for the syn-dihydroxylation of alkenes. Reagent P4 also shows an improved selectivity for dihydroxylation of alkenes bearing β-hydrogens as compared to other CAPs, where both diol and allyl alcohol products compete with each other. Furthermore, the use of enantiopure P4 (labeled P4′) demonstrates the potential of P4′ for a metal-free asymmetric syn-dihydroxylation of alkenes.