(S)-(+)-Glycidyl nosylate
[CAS# 115314-14-2]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon nitrite
• Name: (S)-(+)-Glycidyl nosylate
• Synonyms: (2S)-(+)-Glycidyl 3-nitrobenzenesulfonate; (S)-(+)-Oxirane-2-methanol 3-nitrobenzenesulfonate
• Molecular Formula: C₉H₉NO₆S
• Molecular Weight: 259.23
• CAS Registry Number: 115314-14-2
• EC Number: 621-475-6
• SMILES: C1[C@H](O1)COS(=O)(=O)C2=CC=CC(=C2)[N+](=O)[O-]

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Melting point: 63-66 ºC (Expl.)
• alpha: 21.5 º (c=2, CHCl3)
• Index of Refraction: 1.585, Calc.^*
• Boiling Point: 432.2±20.0 ºC (760 mmHg), Calc.^*
• Flash Point: 215.2±21.8 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Germ cell mutagenicity	Muta.	2	H341
Carcinogenicity	Carc.	2	H351
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Flammable solids	Flam. Sol.	1	H228

Discovory and Applicatios

(S)-(+)-Glycidyl nosylate is a versatile organic compound that has garnered attention in the fields of organic synthesis and medicinal chemistry due to its unique structural features and reactive properties. This compound is a glycidyl derivative, where the glycidyl group is attached to a nosylate (nosyl) anion, a sulfonate ester known for its ability to participate in nucleophilic substitution reactions. The stereochemistry of the compound, specifically the (S)-enantiomer, plays a significant role in its reactivity and application, particularly in the synthesis of chiral molecules. The use of (S)-(+)-glycidyl nosylate is mainly driven by its role as an electrophilic reagent, facilitating the introduction of the glycidyl group into various substrates.

The discovery of (S)-(+)-glycidyl nosylate is part of ongoing efforts to develop new reagents for asymmetric synthesis, a crucial aspect of modern organic chemistry. Glycidyl derivatives, in general, are highly valued for their ability to serve as building blocks in the synthesis of more complex structures. The (S)-configuration of the glycidyl group in this particular compound provides an added advantage in terms of its selective reactivity, which is often desired in the preparation of chiral intermediates for pharmaceutical development. The presence of the nosylate group makes this compound particularly useful in reactions such as nucleophilic substitution, where the leaving group facilitates the transfer of the glycidyl group to a wide range of nucleophiles.

In terms of its application, (S)-(+)-glycidyl nosylate is commonly used in the preparation of glycidyl ethers, esters, and other derivatives, which have a variety of uses in medicinal chemistry, material science, and polymer synthesis. The glycidyl group is highly reactive, allowing it to participate in the formation of covalent bonds with nucleophilic agents, including alcohols, amines, and thiols. This reactivity is particularly important in the creation of chiral compounds, which are critical in the pharmaceutical industry for the development of drugs with high specificity and potency. The ability to introduce a glycidyl group in a controlled manner enables the design of molecules with tailored properties, such as enhanced bioactivity or improved stability.

(S)-(+)-glycidyl nosylate also plays a significant role in the synthesis of chiral epoxy compounds, which are valuable intermediates in the production of agrochemicals, plastics, and other specialty chemicals. In polymer chemistry, glycidyl derivatives are often used to modify the properties of polymers, improving their performance in various applications, such as coatings, adhesives, and electronic components. The ability to selectively functionalize polymers with glycidyl groups offers a way to enhance their chemical resistance, mechanical strength, and thermal stability.

Moreover, the reactivity of (S)-(+)-glycidyl nosylate in nucleophilic substitution reactions extends its potential applications to the creation of advanced drug delivery systems. The glycidyl group can be used to modify the surface properties of nanoparticles or other drug carriers, enabling them to interact more effectively with biological targets. By incorporating (S)-(+)-glycidyl nosylate into drug delivery systems, researchers can improve the bioavailability and controlled release of therapeutic agents.

In conclusion, (S)-(+)-glycidyl nosylate is a valuable compound in the toolkit of synthetic chemists and pharmaceutical developers. Its unique reactivity, combined with the stereochemical selectivity provided by its (S)-configuration, makes it a useful reagent in the synthesis of chiral molecules and functionalized materials. As research continues, the applications of (S)-(+)-glycidyl nosylate are likely to expand, particularly in the development of new pharmaceutical agents and advanced materials with tailored properties.

References

1991. A direct HPLC method for the resolution of glycidyl tosylate and glycidyl 3-nitrobenzenesulphonate enantiomers. Journal of Pharmaceutical and Biomedical Analysis.
DOI: 10.1016/0731-7085(91)80003-r

2005. Chiral Trialkanolamine-Based Hemicryptophanes: Synthesis and Oxovanadium Complex. Organic Letters.
DOI: 10.1021/ol047469+

2003. Indinavir sulfate. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-09-0029