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
• Article Data: 3

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

General Description

(S)-(+)-Glycidyl-4-nitrobenzenesulfonate is a chemical compound that is commonly used in organic synthesis and as a cross-linking agent in polymer chemistry. It is a reactive compound that contains a glycidyl group and a 4-nitrobenzenesulfonate group. The glycidyl group enables it to undergo ring-opening reactions with nucleophiles, making it a useful intermediate in the synthesis of various organic compounds. The nitrobenzenesulfonate group provides stability to the compound, making it a useful reagent for selective functionalization of various substrates. Overall, (S)-(+)-Glycidyl-4-nitrobenzenesulfonate is a versatile chemical that finds utility in a wide range of synthetic applications.

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 
• 60456-23-7 (S)-oxiranemethanol 
• 57044-25-4 (R)-oxiranemethanol 

Downstream Products

• 101693-40-7 (2S)-(+)-3-[4'-(methyl)-phenoxy]-1,2-epoxypropane 
• 310392-57-5 (S)-2-(2'-glycidyloxy)styrylbenzothiazole 
• 310392-60-0 (S)-5-(2-'-glycidyloxystyryl)-3-methyl-1,2,4-oxadiazole 
• 310395-53-0 (S)-α-(2'-(2,3-epoxypropan-1-yloxy)benzylidene)-γ-butyrolactone 
• 310395-75-6 C₁₅H₁₇NO₃ 
• 80910-01-6 (S)-2-[(4-methoxybenzyloxy)methyl]oxirane 
• 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 

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).

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.