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| | (2R)-(-)-Glycidyl tosylate Basic information |
| | (2R)-(-)-Glycidyl tosylate Chemical Properties |
| Melting point | 46-49 °C(lit.) | | Boiling point | 340.07°C (rough estimate) | | alpha | -18 º (c=2.5,CHCl3) | | density | 1.3749 (rough estimate) | | refractive index | 1.5400 (estimate) | | Fp | >230 °F | | storage temp. | 2-8°C | | solubility | dioxane: 50 mg/mL, clear | | form | powder | | color | yellow to orange | | Optical Rotation | -19.9° (C=1 g/100ml CHCL3) | | Water Solubility | decomposes | | BRN | 3592142 | | InChI | InChI=1/C10H12O4S/c1-8-2-4-10(5-3-8)15(11,12)14-7-9-6-13-9/h2-5,9H,6-7H2,1H3/t9-/s3 | | InChIKey | NOQXXYIGRPAZJC-DJEYLCQNNA-N | | SMILES | C1(=CC=C(C)C=C1)S(=O)(=O)OC[C@@H]1OC1 |&1:12,r| | | CAS DataBase Reference | 113826-06-5(CAS DataBase Reference) |
| Hazard Codes | Xn,N,T | | Risk Statements | 45-41-43-51/53-68 | | Safety Statements | 61-45-36/37/39-26-53 | | RIDADR | UN 3077 9/PG 3 | | WGK Germany | 3 | | RTECS | RR0510000 | | F | 3-10-21 | | Hazard Note | Irritant | | HazardClass | 9 | | HS Code | 29109000 | | Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | | Hazard Classifications | Aquatic Chronic 2
Carc. 1B
Eye Dam. 1
Muta. 2
Skin Sens. 1 |
| | (2R)-(-)-Glycidyl tosylate Usage And Synthesis |
| Chemical Properties | white crystalline powder | | Uses | Protected Glycidol, (2R)-(-)-Glycidyl tosylate is used as an intermediate in the preparation of neurochemicals. | | Uses | (2R)-(-)-Glycidyl Tosylate is a protected glycidol used as an intermediate in the preparation of neurochemicals. | | Uses | (2R)-(-)-Glycidyl tosylate may be used to prepare:
- 1-O-hexadecyl-sn-glycerol 3-O-p-toluenesulfonate by reacting with 1-hexadecanol in the presence of boron trifluoride etherate.
- 4-Oxiranylmethoxy-(1H)-indole by reacting with 4-hydroxyindole in the presence of sodium hydride.
- [18F]Epifluorohydin, an intermediate for preparing of [18F]fluoromisonidazole.
It can also be used as a starting material in the synthesis of 1,2-diacyl-sn-3-glycerophosphocholines. | | Synthesis | GENERAL STEPS: Under dry conditions, p-toluenesulfonyl chloride (PTSC, 25.0 g) and (R)-oxirane-2-methanol (6.0 mL) were dissolved in anhydrous dichloromethane (DCM, 250 mL). Subsequently, triethylamine (TEA, 36.0 mL) was added slowly and dropwise at 0°C to the reaction mixture. After the reaction was stirred continuously at 0°C for 3 h, the reaction solution was concentrated by rotary evaporator. The crude product was purified by fast column chromatography (eluent: ethyl acetate/petroleum ether) to afford (R)-p-toluenesulfonic acid glycidyl ester (17.6 g) as a white solid. Yield: 85.0%; Melting point: 44-46°C; [α]D25 = +18.3 (c 1.7, acetonitrile). IR (KBr, cm-1): 1598, 1363, 1177, 969, 666, 556. 1H NMR (400 MHz, DMSO-d6) δ: 7.83 (d, J = 8.1 Hz, 2H), 7.52- 7.46 (m, 2H), 4.43 (d, J = 11.6 Hz, 1H), 3.85 (dddd, J = 7.0, 5.7, 3.7, 1.9 Hz, 1H), 3.26-3.17 (m, 1H), 2.78 (t, J = 4.6 Hz, 1H), 2.66-2.58 (m, 1H), 2.42 (s, 3H). esi -MS m/z: 251.2 [M + Na]+. | | References | [1] Journal of Organic Chemistry, 2015, vol. 80, # 17, p. 8668 - 8676
[2] Chemical Communications, 2014, vol. 50, # 51, p. 6718 - 6721
[3] Organic Letters, 2012, vol. 14, # 11, p. 2834 - 2837
[4] Angewandte Chemie - International Edition, 2014, vol. 53, # 15, p. 3859 - 3862
[5] Angew.Chem.Int.Ed., 2014, vol. 53, p. 3859 - 3862,4 |
| | (2R)-(-)-Glycidyl tosylate Preparation Products And Raw materials |
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