1,2-BIS(TOSYLOXY)ETHANE Chemical Properties

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

2905.31.0000

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1,2-BIS(TOSYLOXY)ETHANE Usage And Synthesis

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

1,2-BIS(TOSYLOXY)ETHANE(6315-52-2)Related Product Information

• 1,2-Bis(chloromethyl)benzene
• 4-Methylbenzyl chloride
• P-XYLENE
• 4-CHLOROMETHYLBENZALDEHYDE; >95%DISCONTINUED 10/25/01
• 1,4-Benzenedimethanol
• 1,3-Bis(chloromethyl)benzene
• 4-(CHLOROMETHYL)BENZYL ALCOHOL 99
• ethylene bis[3,3-bis(3-tert-butyl-4-hydroxyphenyl)butyrate]
• 1,2-Ethanediol, dibenzenesulfonate
• Ethylidene diacetate
• 1,2-BIS(TOSYLOXY)ETHANE
• Ethylene glycol
• ETHYLENE-D4 GLYCOL
• (S)-(-)-1,2-PROPANEDIOL DI-P-TOSYLATE
• METHYL-4,6-O-BENZYLIDENE-2,3-DI-(O-TOSYL)-A-D-GLUCOPYRANOSIDE
• (2S,3S)-2,3-DI-O-TOSYLBUTANEDIOL
• METHYL 4,6-O-BENZYLIDENE-2,3-DI-O-(TOSYL)-ALPHA-D-GLUCOPYRANOSIDE
• CHEMPACIFIC 35909