116204-39-8

Basic information

• Product Name: (R,R)-(+)-1,2-DI(1-NAPHTHYL)-1,2-ETHANEDIOL
• Synonyms: (R,R)-(+)-1,2-DI(1-NAPHTHYL)-1,2-ETHANEDIOL;(R,R)-1,2-DI(1-NAPHTHYL)-1,2-ETHANEDIOL;(R,R)-(+)-1,2-DI(1-NAPTHYL)-1,2-ETHANEDIOL;(R,R)-(+)-1,2-Di(1-naphthyl)-1,2-ethanediol,98%
• CAS NO: 116204-39-8
• Molecular Formula: C₂₂H₁₈O₂
• Molecular Weight: 314.38
• Product Categories: Chiral Compound
• Mol File: 116204-39-8.mol

Chemical Properties

• Melting Point: 149-151 °C(lit.)
• Boiling Point: 549.7°C at 760 mmHg
• Flash Point: 258.5°C
• Appearance: /
• Density: 1.269g/cm³
• Vapor Pressure: 6.47E-13mmHg at 25°C
• Refractive Index: 1.731
• PKA: 13.01±0.20(Predicted)
• CAS DataBase Reference: (R,R)-(+)-1,2-DI(1-NAPHTHYL)-1,2-ETHANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R,R)-(+)-1,2-DI(1-NAPHTHYL)-1,2-ETHANEDIOL(116204-39-8)
• EPA Substance Registry System: (R,R)-(+)-1,2-DI(1-NAPHTHYL)-1,2-ETHANEDIOL(116204-39-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 116204-39-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R,R)-(+)-1,2-DI(1-NAPHTHYL)-1,2-ETHANEDIOL is used as a resolving agent for the production of pharmaceuticals, where its high selectivity in asymmetric reactions is crucial for obtaining optically pure compounds. This purity is essential for the efficacy and safety of many drugs, as different enantiomers can have different biological activities.
Used in Agrochemical Industry:
In the agrochemical sector, (R,R)-(+)-1,2-DI(1-NAPHTHYL)-1,2-ETHANEDIOL is utilized as a chiral auxiliary to synthesize enantiomerically pure agrochemicals. The ability to control the stereochemistry of these compounds is vital for enhancing their target specificity and reducing potential environmental impacts.
Used in Asymmetric Synthesis:
(R,R)-(+)-1,2-DI(1-NAPHTHYL)-1,2-ETHANEDIOL is employed as a chiral auxiliary in asymmetric synthesis, a technique that allows for the preferential formation of one enantiomer over another. This is particularly important in the synthesis of complex molecules where stereochemistry plays a critical role in biological activity.
Used in Fine Chemicals Production:
(R,R)-(+)-1,2-DI(1-NAPHTHYL)-1,2-ETHANEDIOL is also used in the production of other fine chemicals where the control of stereochemistry is necessary to achieve desired properties and reactivity. Its application in this field underscores its versatility and importance in the synthesis of high-value compounds.

InChI:InChI=1/C22H18O2/c23-21(19-13-5-9-15-7-1-3-11-17(15)19)22(24)20-14-6-10-16-8-2-4-12-18(16)20/h1-14,21-24H/t21-,22-/m1/s1

Upstream product

• 66-77-3 1-naphthaldehyde 
• 1233-36-9 (E)-1,2-bis(1-naphthyl)ethene 
• 941-98-0 1'-naphthacetophenone 
• 3457-41-8 1,2-bis(naphthalen-1-yl)ethane-1,2-dione 

Downstream Products

• 159406-53-8 (R,R)-(+)-1,2-di-naphthalen-1-yl-ethane-1,2-diol 
• 229184-99-0 1,2-di(1-naphthyl)ethane-1,2-diol 

Relevant articles and documents

Magnesium-induced pinacol coupling of aromatic aldehydes and ketones under ultrasound irradiation

The system of magnesium and magnesium iodide can reduce some aromatic aldehydes and ketones to the corresponding pinacols in good yields within 10-60 min at room temperature under ultrasound irradiation. Copyright Taylor & Francis, Inc.

Application of coumarin dyes for organic photoredox catalysis

Here we report the application of readily prepared and available coumarin dyes for photoredox catalysis, which are able to mimic powerful reductant [Ir(iii)] complexes. Coumarin derivatives 9 and 10 were employed as photoreductants in pinacol coupling and in other reactions, in the presence of Et3N as a sacrificial reducing agent. As the electronic, photophysical, and steric properties of coumarins could be varied, a wide applicability to several classes of photoredox reactions is predicted.

Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts

An extremely efficient acylative kinetic resolution of d,l-1,2-diols in the presence of only 0.5 mol% of binaphthyl-based chiral N,N-4-dimethylaminopyridine was developed (selectivity factor of up to 180). Several key experiments revealed that hydrogen bonding between the tert-alcohol unit(s) of the catalyst and the 1,2-diol unit of the substrate is critical for accelerating the rate of monoacylation and achieving high enantioselectivity. This catalytic system can be applied to a wide range of substrates involving racemic acyclic and cyclic 1,2-diols with high selectivity factors. The kinetic resolution of d,l-hydrobenzoin and trans-1,2-cyclohexanediol on a multigram scale (10 g) also proceeded with high selectivity and under moderate reaction conditions: (i) very low catalyst loading (0.1 mol%); (ii) an easily achievable low reaction temperature (0 °C); (iii) high substrate concentration (1.0 M); and (iv) short reaction time (30 min). (Figure presented.).

First pinacol coupling in emulsified water: Key role of surfactant and impact of alternative activation technologies

For the first time, the influence of surfactants on the radical pinacol coupling reaction is investigated. The rate and selectivity of this reductive C-C coupling are compared under three different activation technologies: thermal activation, microwave irradiation, and sonication. The use of IgepalCO520, a neutral surfactant, led to the successful conversion of aromatic or α,β-unsaturated aliphatic carbonyl compounds in moderate to excellent yield (55-90 %). An insight on the potential mechanism involved in the reaction is also proposed, based on microscopic observations and particle size measurement.

Selective Pinacol Coupling on Regeneratable Supported Acids in Sole Water

Efficient pinacol coupling was developed in sole water, using a reusable heterogeneous supported acid source and zinc as cheap available metal source. This medium can be easily regenerated up to 10-fold without loss of activity. Moreover, supported acids enhance the selectivity of the pinacol coupling reaction compared with homogeneous acids.

Enantioselective oxidation of 1,2-diols with quinine-derived urea organocatalyst

Quinine-derived urea has been identified as a highly efficient organocatalyst for the enantioselective oxidation of 1,2-diols using bromination reagents as the oxidant. This simple procedure utilizes readily available reagents and operates at ambient temperature to yield a wide range of α-hydroxy ketones in good yield (up to 94%) and excellent enantioselectivity (up to 95% ee).

Titanium(IV) iodide promoted pinacol coupling

Pinacol coupling of aromatic aldehydes was efficiently promoted by titanium tetraiodide in propionitrile to give the 1,2-diol derivatives with high dl-selectivities in high yields.

Highly diastereoselective pinacol coupling of aldehydes catalyzed by titanium-schiff base complexes

A new effective methodology for a highly diastereoselective pinacol coupling of aldehydes is described. The method employes 3 mol % of a complex prepared in situ from TiCl4(THF)2 and a Schiff base in acetonitrile. The catalytic cycle is realized with Me3SiCl and Mn as reducing agent. The dependence of the diastereoselectivity on the Schiff base used is reported.

Magnesium in water: Simple and effective for pinacol-coupling

A simple and effective pinacol-coupling has been carried out with magnesium. The reaction is highly effective in water in the presence of a catalytic amount of ammonium chloride. Under these conditions, various aromatic aldehydes and ketones undergo carbonyl coupling, generating 1,2-diols in good yields. The effectiveness of the reaction is strongly influenced by the steric environment surrounding the carbonyl group. Aliphatic aldehydes appear inert under the reaction conditions.

Conformers and rotamers of (±)-trans-2,3-bis(2-naphthyl)-15-crown-5 and -18-crown-6 and their alkali metal complexes

The conformations of (±)-ira/is-2,3-Bis(1-naphthyl)-15-crown-5 (1) and -18-crown-6 (2) are investigated by MM2 and dynamic 1H-NMR spectroscopy. The most stable conformation is the diequatorial one in both the free ligands and the alkali metal complexes 1·NaClO4 and 2·KClO4, Three rotamers, pseudo-aa, pseudo-ee, and pseudo-ae, with respect to the spatial arrangement of the naphthyl groups, were found as calculated minima by MM2 and experimentally by low-temperature NMR, with fair agreement of the rotational barriers. In the cation-reinforced crowns the rotation rates are significantly diminished. The distribution of the rotamers depends on the size of the crown and its state, free or complexed.