DIETHYLENE GLYCOL BIS(P-TOLUENESULFONATE) Chemical Properties

Melting point:

87-89 °C (lit.)

Boiling point:

581.2±45.0 °C(Predicted)

Density 

1.301±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Solid

color 

Off-White

BRN 

583800

InChI

InChI=1S/C18H22O7S2/c1-15-3-7-17(8-4-15)26(19,20)24-13-11-23-12-14-25-27(21,22)18-9-5-16(2)6-10-18/h3-10H,11-14H2,1-2H3

InChIKey

VYVPNTJBGPQTFA-UHFFFAOYSA-N

SMILES

O(CCOS(C1=CC=C(C)C=C1)(=O)=O)CCOS(C1=CC=C(C)C=C1)(=O)=O

CAS DataBase Reference

7460-82-4(CAS DataBase Reference)

EPA Substance Registry System

Ethanol, 2,2'-oxybis-, bis(4-methylbenzenesulfonate) (7460-82-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2909.30.6000

MSDS

• Language:English Provider:SigmaAldrich

DIETHYLENE GLYCOL BIS(P-TOLUENESULFONATE) Usage And Synthesis

Description

Tos-PEG3-Tos is a PEG linker containing two tosyl groups. The hydrophilic PEG spacer increases solubility in aqueous media. The tosyl group is a very good leaving group for nucleophilic substitution reactions.

Chemical Properties

White to off-white powder

Uses

Diethylene glycol di(p-toluenesulfonate) was used in the synthesis of bis(dibenzosulfoxo)-27,30,35,38-tetramethyl-24-crown-6, bis(dibenzosulfoxo)-21,24,29,32-tetramethyl-18-crown-4, dibenzosulfoxo-15,18-dimethyl-12-crown-3 and dibenzosulfoxo-12,15-dimethyl-9-crown-2 macrocycles.

Synthesis

The general procedure for the synthesis of 2-(2-hydroxyethoxy)ethyl 4-methylbenzenesulfonate and diethylene glycol bis(p-toluenesulfonate) from p-toluenesulfonyl chloride and diethylene glycol was as follows: diethylene glycol (1.25 g, 11.8 mmol) was dissolved in water (3.5 mL), followed by addition of sodium hydroxide (0.768 g, 19.2 mmol). The mixture was stirred at room temperature until a clarified solution was formed. The mixture was cooled to 0 °C and a solution of tetrahydrofuran (30 mL) with 4-toluenesulfonyl chloride (2.27 g, 11.9 mmol) was added slowly and dropwise over 20 minutes. After the dropwise addition was completed, the reaction mixture was continued to be stirred at 0 °C for 1 hour. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (150 mL) and water (40 mL). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and the solvent evaporated under reduced pressure. The residue was purified by a dichloromethane/methanol gradient (100/0 → 100/0) using a Biotage Isolera One purification system on an HP-Sil SNAP column to afford the more polar diethylene glycol bis(p-toluenesulfonate) as a colorless oil (1.47 g, 47% yield). The less polar bis-toluenesulfonyl derivative was discarded.1H-NMR (400 MHz, CDCl3) δ= 7.80 (d, 2H), 7.35 (d, 2H), 4.22-4.18 (m, 2H), 3.72-3.66 (m, 4H), 3.55-3.51 (m, 2H), 2.45 (s, 3H).

IC 50

PEGs

Purification Methods

Purify the ester by recrystallisation from Me2CO and dry it in a vacuum. [Beilstein 11 III 225.]

References

[1] Organic Letters, 2002, vol. 4, # 14, p. 2329 - 2332
[2] Molecules, 2011, vol. 16, # 6, p. 4748 - 4763
[3] Organic Letters, 2002, vol. 4, # 14, p. 2329 - 2332
[4] Drug Design, Development and Therapy, 2018, vol. 12, p. 987 - 995
[5] Patent: WO2015/110263, 2015, A1. Location in patent: Page/Page column 239; 240

DIETHYLENE GLYCOL BIS(P-TOLUENESULFONATE)(7460-82-4)Related Product Information

• Sodium dodecylbenzenesulphonate
• XYLENE CYANOL FF
• Diethylene glycol
• p-Toluenesulfonic acid
• METHYL-2,3,5-TRI-O-(4-TOLYLSULPHONYL)-BETA-D-RIBOFURANOSIDE
• 1-O-ACETYL-5-O-BENZOYL-2,3-DI-O-TOLUOLSULFONYL-D-RIBOFURANOSE
• AURORA KA-659
• 1,6-ANHYDRO-2,4-DI-O-P-TOLUENESULFONYL-BETA-D-GLUCOPYRANOSE
• METHYL-5-O-ACETYL-2,3-DI-O-TOLUOLSULFONYL-BETA-D-RIBOFURANOSIDE
• DIETHYLENE GLYCOL BIS(P-TOLUENESULFONATE)
• 2,3-O-Isopropylidene-1,6-ditosyl-L-sorbose
• 2,3-O-ISOPROPYLIDENE-1,6-DITOSYL-L-SORBOSE