| Identification | More | [Name]
1,2-BIS(TOSYLOXY)ETHANE | [CAS]
6315-52-2 | [Synonyms]
1,2-BIS(P-TOLUENESULFONYLOXY)ETHANE
1,2-BIS(TOSYLOXY)ETHANE
ETHYLENE DITOSYLATE
ETHYLENE GLYCOL BIS-P-TOLUENESULFONATE
ETHYLENE GLYCOL DI-P-TOSYLATE
ETHYLENE GLYCOL DITOSYLATE
Ethylene di(p-toluenesulfonate)
AIDS124301
1,2-ETHANEDIOLBIS(4-METHYLBENZENESULFONATE)
1,2-Bis(4-methylbenzenesulfonyloxy)ethane
1,2-Bis(p-tolylsulfonyloxy)ethane
1,2-Di(tosyloxy)ethane
1,2-Ethanediol 1,2-bis(4-methylbenzenesulfonate):1,2-Ethanediol:1,2-bis(4-methylbenzenesulfonate)
1,2-Ethanediol ditosylate
1,2-Ethylene ditosylate
Di-O-tosylglycol
Ethylene 1,2-bis(tosylate)
Ethylene glycol ditoluenesulfonate
Ethylene glycol ditosylat
Ethylene ditosylate, Ethylene glycol ditosylate | [Molecular Formula]
C16H18O6S2 | [MDL Number]
MFCD00008549 | [Molecular Weight]
370.44 | [MOL File]
6315-52-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Colourless solid | [Melting point ]
124-127 °C(lit.)
| [Boiling point ]
544.3±38.0 °C(Predicted) | [density ]
1.326 | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly), Methanol (Slightly, Heated) | [form ]
Solid | [color ]
White to Off-White | [Water Solubility ]
Slightly soluble in water. | [BRN ]
2399520 | [InChI]
InChI=1S/C16H18O6S2/c1-13-3-7-15(8-4-13)23(17,18)21-11-12-22-24(19,20)16-9-5-14(2)6-10-16/h3-10H,11-12H2,1-2H3 | [InChIKey]
LZIPBJBQQPZLOR-UHFFFAOYSA-N | [SMILES]
C(OS(C1=CC=C(C)C=C1)(=O)=O)COS(C1=CC=C(C)C=C1)(=O)=O | [CAS DataBase Reference]
6315-52-2(CAS DataBase Reference) | [EPA Substance Registry System]
1,2-Ethanediol, bis(4-methylbenzenesulfonate) (6315-52-2) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [HS Code ]
2905.31.0000 |
| Hazard Information | Back Directory | [Chemical Properties]
Colourless solid | [Uses]
Ethylene di(p-toluenesulfonate) [Ethylene glycol ditosylate] has been used in the synthesis of, cyclohexyl-fused 1,4,7-triazacyclononane, 1,2-ethylenecalix[6]arene, 1,3- and 1,4-calix[6]crown-3, 1,3- and 1,4-calix[6]crown-4, 1,4-calix[6]benzocrown-4, 1,2- and 1,3-calix[6]crown-5. | [Synthesis]
The general procedure for the synthesis of 1,2-bis(tolyloxy)ethane from ethylene glycol and p-toluenesulfonyl chloride was as follows: 19.8 g (0.3 mol) of ethylene glycol was dissolved in 150 mL of distilled pyridine, and the solution was subsequently cooled in an ice bath. Under mechanical stirring, p-toluenesulfonyl chloride (123 g, 0.65 mol) was slowly added and it was ensured that the reaction temperature was maintained below 20°C during the addition. When approximately 90 g of p-toluenesulfonyl chloride was added, stirring was difficult due to the increased viscosity of the mixture, at which point 200 mL of pyridine was added for dilution. Stirring of the reaction mixture was continued for 2 hours and 30 minutes. Upon completion of the reaction, an aqueous HCl solution consisting of 12 N HCl (170 mL) and ice (500 mL) was added to the mixture. The solid formed in the process was removed by filtration. The resulting solid was dissolved in 250 mL of refluxing methanol and subsequently filtered to remove the newly formed precipitate after cooling to room temperature. Finally, the obtained white solid was dried under vacuum to give the pure product 1,2-bis-toluoxyethane (92.4 g, 83% yield). The product was characterized as follows: 1H NMR (200 MHz, CDCl3) δ 7.71 (d, 2H), 7.31 (d, 2H), 4.16 (s, 2H), 2.43 (s, 3H). | [References]
[1] Journal of Organic Chemistry, 1992, vol. 57, # 24, p. 6678 - 6680
[2] Synthetic Communications, 1995, vol. 25, # 14, p. 2037 - 2042
[3] Macromolecular Bioscience, 2014, vol. 14, # 12, p. 1807 - 1815
[4] Tetrahedron Letters, 2001, vol. 42, # 50, p. 8781 - 8783
[5] Journal of the Chinese Chemical Society, 2004, vol. 51, # 5 B, p. 1201 - 1208 |
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