Tetraethylene glycol di-p-tosylate Chemical Properties

Melting point:

65-69 °C

Boiling point:

635.0±55.0 °C(Predicted)

Density 

1.242 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.53(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

color 

colorless to yellow

BRN 

1610992

InChI

InChI=1S/C22H30O9S2/c1-19-3-7-21(8-4-19)32(23,24)30-17-15-28-13-11-27-12-14-29-16-18-31-33(25,26)22-9-5-20(2)6-10-22/h3-10H,11-18H2,1-2H3

InChIKey

SLAONPBUWDUSSO-UHFFFAOYSA-N

SMILES

O(CCOCCOS(C1=CC=C(C)C=C1)(=O)=O)CCOCCOS(C1=CC=C(C)C=C1)(=O)=O

EPA Substance Registry System

Ethanol, 2,2'-[oxybis(2,1-ethanediyloxy)]bis-, bis(4-methylbenzenesulfonate) (37860-51-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2909498090

MSDS

• Language:English Provider:SigmaAldrich

Tetraethylene glycol di-p-tosylate Usage And Synthesis

Description

Tos-PEG5-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.

Uses

Tetraethylene glycol di(p-toluenesulfonate), also known as Tetraethylene glycol di-p-tosylate, was used in the preparation of donor-spacer-acceptor podand system, dual channel fluorosensor for Li⁺, Mg²⁺ and Ca²⁺.

Synthesis

20.0 g of tetraethylene glycol triacetonitrile and 10.2 g of triethylamine were added to a reaction flask, 300 mL of acetonitrile was added to dissolve the mixture, and the mixture was cooled to 0-5°C in an ice bath. 19.0 g of p-toluenesulfonyl chloride was dissolved in 100 mL of acetonitrile and slowly added dropwise to the reaction mixture, the dropwise addition time was controlled at 1 hour. After the dropwise addition was completed, the temperature of the reaction mixture was raised to 20-25 °C and the reaction was continued for 12 hours. After completion of the reaction, the solvent was removed by rotary evaporation. The crude product was separated by column chromatography using gradient elution with hexane:ethyl acetate (v/v=4:1) and hexane:ethyl acetate (v/v=1.5:1). In the eluate of hexane:ethyl acetate (v/v=4:1), 12.9 g of oily product (tetraethylene glycol di-p-toluenesulfonate) was obtained in 35.9% yield. In the eluate of hexane:ethyl acetate (v/v=1.5:1), 5.4 g of oily product (tetraethyleneglycol mono-p-toluenesulfonate) was obtained in 10.4% yield.

IC 50

PEGs

storage

Powder: -20°C for 3 years | In solvent: -80°C for 1 year;

References

[1] Organic Letters, 2002, vol. 4, # 14, p. 2329 - 2332
[2] Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 11, p. 2094 - 2100
[3] Zhurnal Organicheskoi Khimii, 1990, vol. 26, # 11, p. 2425 - 2433
[4] Patent: CN105541736, 2016, A. Location in patent: Paragraph 0044; 0052
[5] Journal of the Chemical Society, Perkin Transactions 2, 2001, # 9, p. 1573 - 1584

Tetraethylene glycol di-p-tosylate(37860-51-8)Related Product Information

• Tetraethylene glycol p-toluenesulfonate
• m-PEG5-Tos
• TETRAETHYL METHYLENEDIPHOSPHONATE
• Tetraethylene glycol dimethacrylate
• TETRAETHYLENEGLYCOL MONOMETHYL ETHER
• Tetraethyleneglycol monooctyl ether
• Tos-PEG13-Tos
• Tos-PEG10-CH2CH2COOtBu
• Tos-PEG21-Tos
• Tos-PEG6-t-Butyl ester
• Tos-PEG3-CH2CO2tBu
• Tos-PEG13-t-butyl ester
• Tos-PEG5-CH2CO2t-butyl ester
• Tos-PEG9-t-butyl ester
• Tos-PEG7-t-butyl ester
• Tos-PEG4-t-butyl ester
• (2-{2-[2-(Toluene-4-sulfonyloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid tert-butyl ester
• Tos-PEG7-CH2CO2t-butyl ester