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(S)-(+)-Glycidyl nosylate

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CAS:115314-14-2
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(S)-(+)-Glycidyl nosylate Basic information
Uses
Product Name:(S)-(+)-Glycidyl nosylate
Synonyms:(2S)-OxiranylMethyl 3-Nitrobenzenesulfonate;(S)-Oxiran-2-ylMethyl 3-nitrobenzenesulfonate;(S)-(+)-Glycidyl nosylate, >=98.5%;Glycidyl (S)-(+)-3-nitrobenzenesulfonate;(S)-Glycidyl Nosylate,98%e.e.;(S)-(+)-OXIRANE-2-METHANOL 3-NITROBENZENESULFONATE;(S)-(+)-GLYCIDYL 3-NITROBENZENESULFONATE;(S)-GLYCIDYL 3-NITROBENZENESULFONATE
CAS:115314-14-2
MF:C9H9NO6S
MW:259.24
EINECS:621-475-6
Product Categories:chiral;CHIRAL COMPOUNDS;Chiral Reagents;Heterocycles;Sulfur & Selenium Compounds;APIs Intermediate
Mol File:115314-14-2.mol
(S)-(+)-Glycidyl nosylate Structure
(S)-(+)-Glycidyl nosylate Chemical Properties
Melting point 61-65 °C
alpha 21.5 º (c=2, CHCl3)
Boiling point 432.2±20.0 °C(Predicted)
density 1.5881 (rough estimate)
refractive index 1.5270 (estimate)
storage temp. Inert atmosphere,2-8°C
solubility Soluble in chloroform, methylene chloride and tetrahydrofuran. Insoluble in hexane.
form Needles or Powder
color Off-white to yellow-brown
Sensitive Moisture Sensitive
InChIInChI=1S/C9H9NO6S/c11-10(12)7-2-1-3-9(4-7)17(13,14)16-6-8-5-15-8/h1-4,8H,5-6H2/t8-/m0/s1
InChIKeyAIHIHVZYAAMDPM-QMMMGPOBSA-N
SMILESC1(S(OC[C@@H]2CO2)(=O)=O)=CC=CC([N+]([O-])=O)=C1
CAS DataBase Reference115314-14-2(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38-5
Safety Statements 37/39-26-36
RIDADR UN 1325 4.1/PG II
RTECS DB7192010
HazardClass 4.1
PackingGroup II
HS Code 29209090
MSDS Information
(S)-(+)-Glycidyl nosylate Usage And Synthesis
Uses(S)-(+)-Glycidyl Nosylate is a compound useful in organic synthesis.
Chemical Propertieswhite to light yellow crystal powde
Uses(S)-(+)-Glycidyl Nosylate (cas# 115314-14-2) is a compound useful in organic synthesis.
Synthesis
3-Nitrobenzenesulfonyl chloride

121-51-7

(R)-(+)-Glycidol

57044-25-4

(S)-(+)-Glycidyl nosylate

115314-14-2

General procedure for the synthesis of (S)-(+)-m-nitrobenzenesulfonic acid glycidyl ester from 3-nitrobenzenesulfonyl chloride and (R)-oxirane-2-methanol: at -20 °C, m-nitrobenzenesulfonyl chloride (12.6 g, 57 mmol) was slowly added to a solution containing (R)-(+)-glycidol (5.5 g, 74 mmol) and triethylamine (TEA, 10.3 mL. 74 mmol) in a cold solution. The reaction mixture was stirred continuously at -20 °C for 96 hours. Upon completion of the reaction, the reaction solution was filtered and the filtrate was washed sequentially with 10% (w/w) aqueous tartaric acid, saturated saline and deionized water. The washed organic phase was concentrated to afford the target product (S)-(+)-m-nitrobenzenesulfonic acid glycidyl ester in 97% yield. The structure of the product was confirmed by 1H NMR (CDCl3): δ 2.62 (dd, 1H), 2.84 (dd, 1H), 3.22 (m, 1H), 4.07 (dd, 1H), 4.49 (dd, 1H), 7.80 (t, 1H), 8.25 (m, 1H), 8.52 (m, 1H), 8.78 (m, 1H).

References[1] Angewandte Chemie - International Edition, 2013, vol. 52, # 20, p. 5305 - 5308
[2] Angew. Chem., 2013, vol. 125, # 20, p. 5413 - 5416,4
[3] European Journal of Organic Chemistry, 2014, vol. 2014, # 19, p. 4053 - 4069
[4] Patent: US2004/229900, 2004, A1. Location in patent: Page 14
[5] Organic and Biomolecular Chemistry, 2006, vol. 4, # 16, p. 3067 - 3076
(S)-(+)-Glycidyl nosylate Preparation Products And Raw materials
Raw materials3-Nitrobenzenesulfonyl chloride-->(S)-Oxiranemethanol-->(R)-(+)-Glycidol
Preparation Products(S)-2-Oxiranylanisole
Tag:(S)-(+)-Glycidyl nosylate(115314-14-2) Related Product Information
(R)-Glycidyl butyrate 1-Chloro-3-nitrobenzene ETHYLENE OXIDE Glycidyl tertcarbonate Sodium 3-nitrobenzenesulphonate Methanol 3-Nitrobenzaldehyde 4-Nitrophenyl chloroformate Glycidyl acrylate 3-Nitrobenzenesulfonyl chloride 3-NITROBENZENESULFONIC ACID 2,4,6-TRINITROBENZENESULFONIC ACID Benzenesulfonic acid (R)-(-)-GLYCIDYL NOSYLATE,(R)-GLYCIDYL NOSYLATE 1,3-Dinitrobenzene (R)-(+)-Glycidol Glycidol Glycerol