103548-16-9

Basic information

• Product Name: (R)-1-PHENYL-1,3-PROPANEDIOL
• Synonyms: (R)-PHENYL-1,3-PROPANEDIOL;(R)-1-PHENYL-1,3-PROPANEDIOL;R(+)-1-PHENYL-1,3-PROPANEDIOL;(R)-1-Phenyl-1,3-propanediol,98%
• CAS NO: 103548-16-9
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19
• Product Categories: Chiral Building Blocks;Organic Building Blocks;Polyols
• Mol File: 103548-16-9.mol
• Article Data: 48

Chemical Properties

• Melting Point: 62-66 °C
• Boiling Point: 234.66°C (rough estimate)
• Flash Point: 153.9°C
• Appearance: White/Crystalline Solid
• Density: 1.0505 (rough estimate)
• Vapor Pressure: 0.000255mmHg at 25°C
• Refractive Index: 1.4910 (estimate)
• PKA: 13.95±0.20(Predicted)
• BRN: 4741114
• CAS DataBase Reference: (R)-1-PHENYL-1,3-PROPANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-PHENYL-1,3-PROPANEDIOL(103548-16-9)
• EPA Substance Registry System: (R)-1-PHENYL-1,3-PROPANEDIOL(103548-16-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 103548-16-9(Hazardous Substances Data)

Usage

Description

(R)-1-PHENYL-1,3-PROPANEDIOL, also known as (1R)-1-Phenyl-1,3-propanediol, is a white crystalline solid with unique chemical properties. It is an organic compound that plays a significant role in various chemical reactions and synthesis processes, particularly in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
(R)-1-PHENYL-1,3-PROPANEDIOL is used as a key intermediate in the synthesis and characterization of cytochrome P450 3A-activated prodrugs. These prodrugs are specifically designed for targeting phosph(on)ate-based drugs to the liver, enhancing the efficiency and specificity of drug delivery.
Used in Chemical Synthesis:
In the field of chemical synthesis, (R)-1-PHENYL-1,3-PROPANEDIOL is utilized in the synthesis of 1,3-diols. This is achieved through a diarylprolinol-catalyzed aldol reaction of acetaldehyde with aldehydes, followed by a reduction process. The compound's unique properties make it a valuable asset in creating various chemical products and intermediates.

InChI:InChI=1/C9H12O2/c10-7-6-9(11)8-4-2-1-3-5-8/h1-5,9-11H,6-7H2/t9-/m1/s1

Upstream product

• 58692-70-9 methyl (R)-3-hydroxy-3-phenylpropanoate 
• 72656-47-4 ethyl (R)-3-hydroxy-3-phenylpropanoate 
• 104196-23-8 (2S,3S)-2,3-epoxy-3-phenyl-1-propanol 
• 112763-31-2 (S)-4-benzyloxy-3-methyl-2-butanone 
• 100-52-7 benzaldehyde 
• 72656-48-5 tert-butyl (R)-3-hydroxy-3-phenylpropanoate 
• 139017-16-6 4-phenyl-1-oxa-5-silaspiro<4.5>decane 
• 153562-84-6 3-[(4S,5S)-4,5-Bis(1-methoxycyclopentyl)-1,3,2-dioxoborolan-2-yl]propiophenone 
• 133271-00-8 (R)-3-phenyl-3-hydroxypropanal 
• 104758-27-2 (3'R,4S)-3-(3'-hydroxy-3'-phenylpropionyl)-4-(1-methylethyl)-2-oxazolidinone 
• 212615-53-7 (2R,4R)-2,4-diphenyl-1,3-dioxane 
• 337508-81-3 (2E,5R)-5-hydroxy-5-phenyl-2-pentenoic acid ethyl ester 
• 821775-49-9 (+)-(7R,4E)-7-hydroxy-2,2-dimethyl-7-phenyl-4-hepten-3-one 
• 821775-48-8 (+)-(5R,2E)-5-hydroxy-1,5-diphenyl-2-penten-1-one 

Downstream Products

• 96854-35-2 (3R)-3-hydroxy-3-phenylpropyl pivalate 
• 139054-14-1 (2R,6R,8R,9S)-4-phenyl-8,9-dimethyl-1,5,7-trioxaspiro<5.5>undecane 
• 139054-14-1 (4R,6R,8S,9R)-4-phenyl-8,9-dimethyl-1,5,7-trioxaspiro<5.5>undecane 
• 139054-20-9 (2R,6R,9R)-4-phenyl-9-ethyl-1,5,7-trioxaspiro<5.5>undecane 
• 139054-20-9 (4R,6R,9S)-4-phenyl-9-ethyl-1,5,7-trioxaspiro<5.5>undecane 
• 139054-22-1 (2R,6R,8S)-4-phenyl-8-n-hexyl-1,5,7-trioxaspiro<5.5>undecane 
• 139054-22-1 (4R,6R,8R)-4-phenyl-8-n-hexyl-1,5,7-trioxaspiro<5.5>undecane 
• 103574-68-1 (R)-1-phenylpropane-1,3-diol mono-t-butyldimethylsilyl ether 
• 865777-22-6 (R)-3-methoxy-3-phenyl-propionaldehyde 
• 865789-42-0 (R)-3-Methoxy-3-phenyl-propan-1-ol 
• 865777-21-5 tert-butyl-(3-methoxy-3-phenyl-propoxy)-dimethyl-silane 
• 54910-89-3 (R)-fluoxetine 
• 115290-81-8 (R)-N-methyl-3-phenyl-3-hydroxypropylamine 

Relevant articles and documents

A general synthesis of homochiral β-hydroxy N-acetylcysteamine thioesters

A convenient and efficient route for the enantioselective synthesis of functionalised β-hydroxy N-acetylcysteamine thioesters is described. The route allows the facile incorporation of vicinal 13C labelling to produce intermediates required for biosynthetic studies on a wide range of polyketide metabolites, e.g. 6-MSA, monocerin, colletodiol and strobilurins.

Directed Asymmetric Reduction of a Carbonyl Group via a New Homochiral Boronate Ester

Homochiral β-boronate carbonyl derivative 4 directs the asymmetric reduction of the ketone moiety, providing 89percent enantiomeric excess of the (S)-diol 6, using borane-tetrahydrofuran as the reducing agent.

Asymmetric catalysis. Asymmetric catalytic intramolecular hydrosilation and hydroacylation

Catalysts of the type [Rh(chiral diphosphine)]+ efficiently catalyse the intramolecular hydrosilation of silyl ethers derived from allylic alcohols. The products can be converted to chiral 1,3-diols. High enantiomeric excesses (ee's) are observ

Enantioselective synthesis of (+)-sedamine and (-)-allosedamine

Two different approaches to the enantioselective syntheses of (+)-sedamine and (-)-allosedamine are described, both using the Sharpless asymmetric epoxidation as the key step. Regioselective reduction of epoxides, chemoselective oxidation of alcohols, ring-closing metathesis, and nucleophilic displacements were the other key steps employed. Georg Thieme Verlag Stuttgart.

A site isolation-enabled organocatalytic approach to enantiopure γ-amino alcohol drugs

Solid support-enabled site isolation has previously allowed to use paraldehyde as an acetaldehyde surrogate in aldol reactions. However, only electron-poor aldehydes were tolerated by the system. Herein, we show that the temporary conversion of benzaldehyde into η6-benzaldehyde Cr(CO)3 circumvents this limitation. Asymmetric synthesis of (R)-Phenoperidine, as well as formal syntheses of (R)-Fluoxetine and (R)-Atomoxetine, illustrate the benefits of this strategy.

Enantioselective β-hydroxy thioesters formation via decarboxylative aldol reactions of malonic acid half thioesters with aldehydes promoted by chloramphenicol derived sulfonamides

A highly enantioselective synthesis of chiral β-hydroxy thioesters that uses a decarboxylative aldol reaction of malonic acid half thioesters and aldehydes catalyzed by a chloramphenicol base-derived bifunctional organocatalyst is reported. The resulting

The Catalytic Asymmetric Intermolecular Prins Reaction

Despite their significant potential, catalytic asymmetric reactions of olefins with formaldehyde are rare and metal-free approaches have not been previously disclosed. Here we describe an enantioselective intermolecular Prins reaction of styrenes and paraformaldehyde to form 1,3-dioxanes, using confined imino-imidodiphosphate (iIDP) Br?nsted acid catalysts. Isotope labeling experiments and computations suggest a concerted, highly asynchronous addition of an acid-activated formaldehyde oligomer to the olefin. The enantioenriched 1,3-dioxanes can be transformed into the corresponding optically active 1,3-diols, which are valuable synthetic building blocks.

Chiral Ion-Pair Organocatalyst-Promoted Efficient Enantio-selective Reduction of α-Hydroxy Ketones

The enantioselective reduction of α-hydroxy ketones with catecholborane has been developed employing 5 mol% of an 1,1′-bi-2-naphthol (BINOL)-derived ion-pair organocatalyst. This methodology provides a straightforward access to the corresponding aromatic 1,2-diols in high yields (up to 90%) with excellent enantioselectivities (up to 97%). Furthermore, the α-amino ketones also could be reduced with moderate ee values under mild reaction condition. (Figure presented.).