Choline tosylate Chemical Properties

Melting point:

95°C

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

crystalline solid

color 

White

Sensitive 

Light Sensitive/Hygroscopic

InChI

InChI=1S/C7H8O3S.C5H14NO/c1-6-2-4-7(5-3-6)11(8,9)10;1-6(2,3)4-5-7/h2-5H,1H3,(H,8,9,10);7H,4-5H2,1-3H3/q;+1/p-1

InChIKey

DVGVMQVOCJNXNJ-UHFFFAOYSA-M

SMILES

C1(S([O-])(=O)=O)C=CC(C)=CC=1.C(CO)[N+](C)(C)C

CAS DataBase Reference

55357-38-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant/Hygroscopic/Light Sensitive

HS Code 

2923900090

MSDS

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

Choline tosylate Usage And Synthesis

Uses

Choline p-Toluenesulfonate Salt is a useful intermediate as well as a choline acetyltransferase (CHAT) substrate.

Synthesis

A 500 mL reactor was charged at 25 ??C with 50 g (268.5 mmol) methyl tosylate and 100 mL acetone to which a solution of 25.1 g (281.6 mmol) N,N-dimethyl ethanolamine in 50.3 g acetone was added continuously at 25 ??C over 3 h. The dropping funnel was rinsed with additional acetone. The reaction mixture was stirred at 25 ??C for 20 h and the reaction progress was monitored by HPLC. When the level of methyltosylate was lower than 500 ppm the resulting suspension was cooled to 0 ??C over 150 min and the suspension was stirred at 0 ??C for 60 min. The product was collected by fdtration, washed two times with 175 mL acetone and dried under vacuum at 25 ??C to obtain 73.1 g (99 %) of choline tosylate as a white crystalline solid.

References

[1] Russian Chemical Bulletin, 1998, vol. 47, # 8, p. 1547 - 1549
[2] Tetrahedron Letters, 2009, vol. 50, # 28, p. 4092 - 4095
[3] Patent: JP5751578, 2015, B2. Location in patent: Paragraph 0017
[4] European Journal of Medicinal Chemistry, 2009, vol. 44, # 12, p. 4970 - 4977
[5] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1988, vol. 37, p. 2293 - 2296

Choline tosylate(55357-38-5)Related Product Information

• Methyl p-toluenesulfonate
• p-Toluenesulfonic acid
• Choline chloride
• Sodium xylenesulfonate
• Sodium p-toluenesulfonate
• Ethyl p-toluenesulfonate
• 4-CHLOROBENZOYLACETONITRILE
• Sodium isethionate
• Choline hydroxide
• CHLOROPHOSPHONAZO III
• PROPIONYLCHOLINE P-TOLUENESULFONATE
• 1-CYCLOHEXYL-3-(2-MORPHOLINOETHYL)CARBODIIMIDE METHO-P-TOLUENESULFONATE
• METHACRYLOYL OXYETHYL TRIMETHYL AMMONIUM P-TOLUENESULFONATE
• p-Toluenesulfonic acid ammonium salt
• Choline tosylate
• AKOS 90521
• ETHANAMINIUM, N-(2-FLUOROETHYL)-2-HYDROXY-N,N-DIMETHYL-, SALT WITH 4-METHYLBENZENESULFONIC ACID