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| | (R)-(-)-Glycidyl nosylate Basic information |
| | (R)-(-)-Glycidyl nosylate Chemical Properties |
| Melting point | 59-63 °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 | Chloroform (Slightly), DMSO (Slightly) | | form | Crystalline Needles or Powder | | color | Slightly yellow | | Optical Rotation | -22.001°(C=1.00 g/100ml, CHCL3) | | InChI | InChI=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-/m1/s1 | | InChIKey | AIHIHVZYAAMDPM-MRVPVSSYSA-N | | SMILES | C1(S(OC[C@H]2CO2)(=O)=O)=CC=CC([N+]([O-])=O)=C1 | | CAS DataBase Reference | 115314-17-5(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 37/39-26-36 | | RIDADR | UN 1325 4.1/PG II | | RTECS | DB7192000 | | HazardClass | 4.1 | | PackingGroup | II | | HS Code | 29209090 |
| | (R)-(-)-Glycidyl nosylate Usage And Synthesis |
| Chemical Properties | white to light yellow crystal powde | | Uses | (R)-(-)-Glycidyl Nosylate (cas# 115314-17-5) is a compound useful in organic synthesis. | | Synthesis | Preparation of Compound 3: To an anhydrous dichloromethane (10 mL) and triethylamine (1.5 mL, 10 mmol) solution of (S)-oxiran-2-ylmethanol (220 mg, 3.0 mmol) that had been cooled to 0 °C (ice bath), 3-nitrobenzenesulfonyl chloride (730 mg, 3.3 mmol) was added in batches. The resulting brown solution was stirred at 0 °C for 1 h, followed by slow warming to room temperature. The progress of the reaction was monitored by TLC every 15 min until (S)-oxiran-2-ylmethanol was completely consumed. Upon completion of the reaction, the reaction was quenched by the addition of crushed ice (1-2 g). The reaction mixture was transferred to a dispensing funnel and partitioned with dichloromethane (20 mL) and water (10 mL). The organic layer was washed sequentially with saturated aqueous NaHCO3 (10 mL x 3) and brine (10 mL x 3), followed by drying with anhydrous Na2SO4. After filtration and concentration, the residue was purified by fast column chromatography to afford (S)-(+)-m-nitrobenzenesulfonic acid glycidyl ester (Compound 3) as a brown solid (710 mg, 92%).1H NMR (400 MHz, CDCl3) δ 8.77 (s, 1H), 8.54 (d, J=8.1 Hz, 1H), 8.28 (d, J=7.9 Hz , 1H), 4.50 (d, J=11.5Hz, 1H), 4.04 (dd, J1=4.9Hz, J2=1.5Hz, 1H), 3.23 (d, J=1.8Hz, 1H), 2.85 (dd, J1=4.0Hz, J2=2.0Hz, 1H), 2.64 (dd, J1=2.4Hz, J2=2.0Hz, 1H) 1H); 13C NMR (100 MHz, CDCl3) δ 148.19, 137.92, 133.32, 130.81, 128.39, 123.16, 71.69, 48.64, 44.42. | | References | [1] Patent: US2009/182011, 2009, A1. Location in patent: Page/Page column 13
[2] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 9, p. 656 - 661
[3] Tetrahedron, 2009, vol. 65, # 31, p. 5984 - 5989
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 8, p. 2948 - 2950
[5] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 17, p. 4792 - 4802 |
| | (R)-(-)-Glycidyl nosylate Preparation Products And Raw materials |
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