40434-87-5

Basic information

• Product Name: (R)-(-)-1-PHENYL-1,2-ETHANEDIOL 2-TOSYLATE
• Synonyms: (R)-(-)-2-HYDROXY-2-PHENYLETHYL P-TOLUENESULFONATE;(R)-(-)-1-PHENYL-1,2-ETHANEDIOL 2-TOSYLATE;(R)-(-)-1-PHENYLETHANEDIOL 2-TOSYLATE;2-hydroxy-2-phenylethyl [R-(-)]-p-toluenesulphonate;(R)-(-)-1-PHENYL-1,2-ETHANEDIOL 2-TOSYLATE, 98+%;(-)-p-Toluenesulfonic acid (R)-2-hydroxy-2-phenylethyl ester;p-Toluenesulfonic acid (R)-β-hydroxyphenethyl ester;(R)-(-)-2-Hydroxy-2-phenylethyl 4-methylbenzenesulfonate
• CAS NO: 40434-87-5
• Molecular Formula: C₁₅H₁₆O₄S
• Molecular Weight: 292.35
• EINECS: 254-918-3
• Mol File: 40434-87-5.mol
• Article Data: 29

Chemical Properties

• Melting Point: 79-81°C
• Boiling Point: 480.6 °C at 760 mmHg
• Flash Point: 244.5 °C
• Appearance: /
• Density: 1.274 g/cm³
• Vapor Pressure: 4.77E-10mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.95±0.20(Predicted)
• BRN: 5755931
• CAS DataBase Reference: (R)-(-)-1-PHENYL-1,2-ETHANEDIOL 2-TOSYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-1-PHENYL-1,2-ETHANEDIOL 2-TOSYLATE(40434-87-5)
• EPA Substance Registry System: (R)-(-)-1-PHENYL-1,2-ETHANEDIOL 2-TOSYLATE(40434-87-5)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 40434-87-5(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

InChI:InChI=1/C15H16O4S/c1-12-7-9-14(10-8-12)20(17,18)19-11-15(16)13-5-3-2-4-6-13/h2-10,15-16H,11H2,1H3

Upstream product

• 96-09-3 styrene oxide 
• 104-15-4 toluene-4-sulfonic acid 
• 40434-87-5 toluene-4-sulfonic acid 2-hydroxy-2-phenylethyl ester 
• 22651-87-2 cyclohexanecarboxylic acid anhydride 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 98-59-9 p-toluenesulfonyl chloride 
• 100-52-7 benzaldehyde 
• 100-42-5 styrene 
• 7257-94-5 1-phenyl-2-(p-tolylsulfonyloxy)ethanone 
• 611-71-2 (R)-Mandelic Acid 
• 27126-76-7 [hydroxy(tosyloxy)iodo]benzene 
• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 
• 93-56-1 phenylethane 1,2-diol 
• 61235-70-9 (+/-)4-phenyl-2,2-di-n-butyl-1,3,2-dioxa stannolan 

Downstream Products

• 127840-18-0 Acetic acid (S)-1-phenyl-2-(toluene-4-sulfonyloxy)-ethyl ester 
• 1445-91-6 (S)-1-phenylethanol 
• 106760-65-0 (1R)-2-N<(S)-1-phenylethyl>amino-1-phenylethanol 
• 110901-04-7 (R,R)-2-(1-phenylethyl)amino-1-phenylethanol 
• 134625-72-2 (R)-2-azido-1-phenylethanol 
• 194922-77-5 (R)-2-((R,R)-2-methoxy-1,2-diphenylethoxy)-1-phenylethanol 
• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 
• 4427-92-3 (4S)-4-phenyl[1,3]dioxolan-2-one 
• 1517-69-7 (R)-1-phenylethanol 
• 945985-19-3 C₂₁H₃₀O₄SSi 
• 945985-20-6 C₂₁H₂₆O₅ 
• 73627-97-1 (R)-3-phenyl-3-hydroxypropanenitrile 
• 1258048-39-3 C₂₀H₂₂O₆S 
• 40435-14-1 (S)-1-phenyl-2-(tosyloxy)ethanol 

Relevant articles and documents

Chiral guanidine catalyzed acylative kinetic resolution of racemic 2-bromo-1-arylethanols

In this study, chiral guanidine catalyzed acylative kinetic resolution of racemic 2-bromo-1-arylethanols was achieved with high selectivity. Irrespective of the electronic nature and the substitution patterns on the aromatic rings, a variety of substrates were suitable for this reaction. The branched acyl component was considered to be optimal for obtaining high s-values. The transition state of the reaction was proposed based on the absolute configuration of the obtained product.

Selective Asymmetric Transfer Hydrogenation of α-Substituted Acetophenones with Bifunctional Oxo-Tethered Ruthenium(II) Catalysts

A practical method for the asymmetric transfer hydrogenation of α-substituted ketones was developed utilizing oxo-tethered N-sulfonyldiamine-ruthenium complexes. Reduction by HCO2H and HCO2K in a mixed solvent of EtOAc/H2O allowed for the selective synthesis of halohydrins from 2-bromoacetophenone (98%) and 2-chloroacetophenone (>99%), leading to suppressed undesired side reactions stemming from formylation under the typical reaction conditions using an azeotropic 5:2 mixture of HCO2H and Et3N. A range of functional groups, such as halogens, methoxy, nitro, dimethylamino, and ester groups, were well tolerated, highlighting the potential of this method. Nearly complete selectivity with a preferable ee was maintained even with a substrate/catalyst (S/C) ratio of 5000. This catalyst system was also effective for the asymmetric reduction of α-sulfonated ketones without eroding the leaving group. (Figure presented.).

Study on a New Method for Synthesis of Mirabegron

Mirabegron is a muscle relaxing drug for the treatment of overactive bladder. The existing synthetic methods for mirabegron produced intermediate product 4-(2-(phenethylamino)ethyl)aniline, which complicated the final product purification process. In this study, we designed a new synthetic route for mirabegron with low cost starting materials and a production of mirabegron at a 99.6% purity and a 61% overall yield. Particularly, this new synthetic route did not produce side product 4-(2-(phenethylamino)ethyl)aniline, which significantly simplified the product purification process.