49801-14-1

Basic information

• Product Name: (R)-(-)-1-(2-NAPHTHYL)-1,2-ETHANEDIOL
• Synonyms: (R)-(-)-1-(2-NAPHTHYL)-1,2-ETHANEDIOL;(R)-(-)-1-(2-NAPHTHYL)-1,2-ETHANEDIOL, 9 8%
• CAS NO: 49801-14-1
• Molecular Formula: C₁₂H₁₂O₂
• Molecular Weight: 190.24
• Mol File: 49801-14-1.mol

Chemical Properties

• Melting Point: 131-135 °C(lit.)
• Boiling Point: 402.3°Cat760mmHg
• Flash Point: 202.3°C
• Appearance: /
• Density: 1.237g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.668
• CAS DataBase Reference: (R)-(-)-1-(2-NAPHTHYL)-1,2-ETHANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-1-(2-NAPHTHYL)-1,2-ETHANEDIOL(49801-14-1)
• EPA Substance Registry System: (R)-(-)-1-(2-NAPHTHYL)-1,2-ETHANEDIOL(49801-14-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 49801-14-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
(R)-(-)-1-(2-NAPHTHYL)-1,2-ETHANEDIOL is used as a chiral auxiliary in asymmetric synthesis for the preparation of chiral alcohols and amines. Its unique structure allows for the creation of enantiomerically pure compounds, which are crucial in the development of pharmaceuticals with specific biological activities.
Used in Chemical Synthesis:
In the field of chemical synthesis, (R)-(-)-1-(2-NAPHTHYL)-1,2-ETHANEDIOL serves as a resolving agent for racemic mixtures. This role is essential for separating enantiomers, which can exhibit different properties and effects, thus enabling the production of more effective and targeted chemical compounds.
Used in Drug Development:
(R)-(-)-1-(2-NAPHTHYL)-1,2-ETHANEDIOL is also utilized in drug development due to its potential pharmacological properties. It has been investigated for its role as a therapeutic agent in various diseases, highlighting its versatility and importance in the advancement of medical treatments.

InChI:InChI=1/C12H12O2/c13-8-12(14)11-6-5-9-3-1-2-4-10(9)7-11/h1-7,12-14H,8H2/t12-/m0/s1

Upstream product

• 86457-71-8 2-(naphthalen-2-yl)oxirane 
• 43210-74-8 (+/-)-1-(2-naphthalenyl)-ethane-1,2-diol 
• 98-88-4 benzoyl chloride 
• 100-52-7 benzaldehyde 

Downstream Products

• 153875-87-7 (+/-)-2-amino-2-(2-naphthalenyl)-ethanol 
• 43210-74-8 (S)-1-(naphthalen-2-yl)-1,2-ethanediol 
• 191109-49-6 (S)-2-amino-2-(β-naphthyl)-1-ethanol 
• 204851-80-9 (R)-2-amino-2-(2-naphthyl)ethanol 
• 354153-57-4 (S)-2-Hydroxy-N-((R)-2-hydroxy-1-naphthalen-2-yl-ethyl)-2-phenyl-acetamide 
• 354153-61-0 (S)-2-Hydroxy-N-((S)-2-hydroxy-1-naphthalen-2-yl-ethyl)-2-phenyl-acetamide 
• 93-09-4 naphthalene-2-carboxylate 
• 542-52-9 Dibutyl carbonate 
• 174198-96-0 4-(naphthalen-2-yl)-1,3-dioxolan-2-one 
• 827-54-3 2-naphthylethylene 
• 33741-78-5 DL-2-Amino-2-(2-naphthyl)acetic acid 
• 66-99-9 β-naphthaldehyde 
• 156942-67-5 (R)-α-methoxynaphthalen-2-ylacetic acid 

Relevant articles and documents

Kinetic Resolution of 1,2-Diols via NHC-Catalyzed Site-Selective Esterification

A kinetic resolution of 1,2-diols bearing both a secondary and a primary alcohol motif through an N-heterocyclic carbene-catalyzed oxidative acylation reaction has been developed. A site- and enantioselective esterification reaction is involved for this process. Both the monoacylated diols obtained and the remaining enantioenriched 1,2-diols are versatile building blocks for the preparation of functional molecules with proven biological activities.

Method for the dihydroxylation of olefins using transition metal catalysts

This invention relates to process for dihydroxylation of olefins using transition metal catalysts to obtain monofunctional, bifunctional, and/or polyfunctional 1,2-diols of the formula (I) R1R2C(OH)—C(OH)R3R4??(I) where R1to R4are defined herein, by reacting an olefin of the formula (II) R1R2C═CR3R4??(II) where R1to R4are defined as for formula (I), with molecular oxygen in the presence of an osmium, ruthenium, or manganese compound in water or a water-containing solvent mixture at a pH of from 7.5 to 13.

Nonenzymatic kinetic resolution of 1,2-diols catalyzed by an organotin compound

(matrix presented) A new nonenzymatic kinetic resolution method of 1,2-diols 1 using chiral organotin catalyst A with benzoyl chloride was developed. A remarkable effect due to an inorganic base such as sodium carbonate and a small portion of water on the ee of the main products 2 was observed. The reaction showed high enantio-and chemoselectivities to 1,2-diols 1.

Bismuth(III)-catalyzed oxidative cleavage of aryl epoxides: substituent effects on the kinetics of the oxidation reaction

Bismuth(III)mandelate catalyzes the oxidative C-C bond cleavage of a series of styrene epoxides in DMSO, to the corresponding aryl carboxylic acids.The reaction is accelerated in the presence of electron-donating groups substituting the phenyl ring.A good Hammet correlation of log kobs versus ? has been obtained, with a ρ of -1.08.Key words: Bismuth; Aryl epeoxide cleavage; Oxidation; Substituent effects; Bi(III) catalysis; Hammet correlation