118712-60-0

Basic information

• Product Name: (S)-(+)-Glycidyl-4-nitrobenzenesulfonate
• Synonyms: (2S)-(+)-GLYCIDYL 4-NITROBENZOATE;(S)-(+)-GLYCIDYL-4-NITROBENZOATE;(S)-(+)-GLYCIDYL-4-NITRO BENZENESULFONATE;(S)-(+)-GLYCIDYL-4-NITRO BENZENESULFONATE 99+%;(S)-oxiran-2-ylmethyl 4-nitrobenzenesulfonate;(S)-Glycidil-4-Nosylate;(S)-Glycidyl-4-nosylate;(S)-Glycidyl 4-Nitrobenzenesulfonate
• CAS NO: 118712-60-0
• Molecular Formula: C₉H₉NO₆S
• Molecular Weight: 259.24
• Mol File: 118712-60-0.mol

Chemical Properties

• Melting Point: 60-62 °C(lit.)
• Boiling Point: 440.309 °C at 760 mmHg
• Flash Point: 220.091 °C
• Appearance: /
• Density: 1.527 g/cm³
• Vapor Pressure: 1.54E-07mmHg at 25°C
• Refractive Index: 1.585
• Storage Temp.: 2-8°C
• Solubility: slightly sol. in Chloroform
• CAS DataBase Reference: (S)-(+)-Glycidyl-4-nitrobenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-Glycidyl-4-nitrobenzenesulfonate(118712-60-0)
• EPA Substance Registry System: (S)-(+)-Glycidyl-4-nitrobenzenesulfonate(118712-60-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 1325 4.1/PG II
• WGK Germany: 3
• RTECS: RR0511020
• F: 10-21
• HazardClass: 4.1
• PackingGroup: II
• Hazardous Substances Data: 118712-60-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(S)-(+)-Glycidyl-4-nitrobenzenesulfonate is used as a versatile intermediate in organic synthesis for the preparation of various organic compounds. Its glycidyl group facilitates ring-opening reactions with nucleophiles, allowing for the formation of new chemical bonds and the synthesis of complex molecules.
Used in Polymer Chemistry as a Cross-linking Agent:
In the polymer industry, (S)-(+)-Glycidyl-4-nitrobenzenesulfonate is utilized as a cross-linking agent to enhance the mechanical properties and stability of polymers. Its ability to form covalent bonds between polymer chains results in improved strength, rigidity, and thermal resistance.
Used in Pharmaceutical Industry:
(S)-(+)-Glycidyl-4-nitrobenzenesulfonate is employed as a key building block in the synthesis of pharmaceutical compounds. Its unique reactivity and selectivity enable the development of novel drug candidates with potential therapeutic applications.
Used in Chemical Research:
In the field of chemical research, (S)-(+)-Glycidyl-4-nitrobenzenesulfonate serves as a valuable tool for studying reaction mechanisms and exploring new synthetic methodologies. Its reactivity and stability make it an ideal candidate for investigating various chemical transformations and understanding the underlying principles.
Used in Material Science:
(S)-(+)-Glycidyl-4-nitrobenzenesulfonate is applied in material science for the development of advanced materials with tailored properties. Its ability to form cross-links and participate in various chemical reactions allows for the creation of materials with improved performance in areas such as electronics, coatings, and adhesives.

InChI:InChI=1/C9H9NO6S/c11-10(12)7-1-3-9(4-2-7)17(13,14)16-6-8-5-15-8/h1-4,8H,5-6H2/t8-/m0/s1

Upstream product

• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 57044-25-4 (R)-oxiranemethanol 
• 60456-23-7 (S)-oxiranemethanol 

Downstream Products

• 99103-03-4 (-)-Bisoprolol 
• 101623-41-0 (2S)-3-(3-methylphenoxy)-1,2-epoxypropane 
• 400801-26-5 5-methanesulfonyl-1-((R)-oxiranylmethyl)-3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine 
• 125279-82-5 (S)-1,2-epoxy-3-(4-nitrophenoxy)propane 
• 159182-09-9 3-(4-tert-butyldimethylsilyloxyphenoxy)-2-(S)-propyleneoxide 
• 886041-53-8 3-cyclohexyl-2-{2-[(2S)-oxiran-2-ylmethoxy]phenyl}-1H-indole-6-carboxylic acid methyl ester 
• 80910-01-6 (S)-2-[(4-methoxybenzyloxy)methyl]oxirane 
• 310395-75-6 C₁₅H₁₇NO₃ 
• 310395-53-0 (S)-α-(2'-(2,3-epoxypropan-1-yloxy)benzylidene)-γ-butyrolactone 

Relevant articles and documents

Initial development of a cytotoxic amino-seco-CBI warhead for delivery by prodrug systems

Abstract Cyclopropabenzaindoles (CBIs) are exquisitely potent cytotoxins which bind and alkylate in the minor groove of DNA. They are not selective for cancer cells, so prodrugs are required. CBIs can be formed at physiological pH by Winstein cyclisation of 1-chloromethyl-3-substituted-5-hydroxy-2,3-dihydrobenzo[e]indoles (5-OH-seco-CBIs). Corresponding 5-NH2-seco-CBIs should also undergo Winstein cyclisation similarly. A key triply orthogonally protected intermediate on the route to 5-NH2-seco-CBIs has been synthesised, via selective monotrifluoroacetylation of naphthalene-1,3-diamine, Boc protection, electrophilic iodination, selective allylation at the trifluoroacetamide and 5-exo radical ring-closure with TEMPO. This intermediate has potential for introduction of peptide prodrug masking units (deactivating the Winstein cyclisation and cytotoxicity), addition of diverse indole-amide side-chains (enhancing non-covalent binding prior to alkylation) and use of different leaving groups (replacing the usual chlorine, allowing tuning of the rate of Winstein cyclisation). This key intermediate was elaborated into a simple model 5-NH2-seco-CBI with a dimethylaminoethoxyindole side-chain. Conversion to a bio-reactive entity and the bioactivity of this system were confirmed through DNA-melting studies (ΔTm = 13°C) and cytotoxicity against LNCaP human prostate cancer cells (IC50 = 18 nM).

PROCESS FOR THE PREPARATION OF CATHEPSIN S INHIBITORS

Inhibitors of Cathepsin S enzyme and their synthetic processes.

Arenesulfonate Derivatives of Homochiral Glycidol: Versatile Chiral Building Blocks for Organic Synthesis

The preparation of a series of crystalline arenesulfonate derivatives of enantiomerically enriched glycidol is described.The enhancement of optical purity by recrystallization was particularly successful for two of these derivatives, glycidyl tosylate and glycidyl 3-nitrobenzenesulfonate, which were obtained in 97 percent ee and 99 percent ee, respectively.Very high regioselectivity was observed in the reactions of these compounds with a variety of nucleophiles, including aryl oxides, Et2AlCN, organometallic reagents, and BH3-NaBH4.The application of this methodology to the synthesis of homochiral β-adrenergic blocking agents and homochiral terminal epoxides is discussed.