N-BUTYL METHANESULPHONATE Chemical Properties

Boiling point:

172°C (estimate)

Density 

1.088 (estimate)

refractive index 

1.5151 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

solid

color 

Colourless to Pale Yellow

InChI

InChI=1S/C5H12O3S/c1-3-4-5-8-9(2,6)7/h3-5H2,1-2H3

InChIKey

LFLBHTZRLVHUQC-UHFFFAOYSA-N

SMILES

CS(OCCCC)(=O)=O

CAS DataBase Reference

1912-32-9(CAS DataBase Reference)

EPA Substance Registry System

Methanesulfonic acid, butyl ester (1912-32-9)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36-43-36/37/38

Safety Statements 

26-36/37-37

RTECS 

PB1425000

HS Code 

29049090

N-BUTYL METHANESULPHONATE Usage And Synthesis

Uses

Butyl Methanesulfonate is a reactant used in the preparation of task-specific ionic liquids.

Synthesis

To an anhydrous dichloromethane (10 mL) solution of n-butanol (500 mg, 6.7 mmol) was added sequentially pyridine (0.82 mL, 10.1 mmol) and methanesulfonyl chloride (0.78 mL, 10.1 mmol). The reaction mixture was stirred at 0 °C and gradually warmed to room temperature. After 6 hours of reaction, the reaction was quenched with methanol and the reaction solution was subsequently concentrated. The concentrate was diluted with ethyl acetate (50 mL) and washed sequentially with 1 M hydrochloric acid (10 mL), saturated sodium bicarbonate solution (10 mL) and saturated saline (10 mL). The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel column chromatography to afford n-butyl methanesulfonate (compound 2) as a colorless oil (0.94 g, 92% yield).1H NMR (400 MHz, CDCl3) δ 4.24 (t, J = 13.2, 6.4 Hz, 2H), 3.01 (s, 3H), 1.76-1.72 (m, 2H), 1.48- 1.42 (m, 2H), 0.96 (t, J = 12.8, 7.6 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 69.99, 37.30, 31.05, 18.67, 13.48. High-resolution mass spectrometry (ESI) calculated value [C5H12SO3 + Na]+ 175.0405, measured value 175.0401.

References

[1] Journal of the Indian Chemical Society, 2009, vol. 86, # 8, p. 841 - 848
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 41, p. 7753 - 7759
[3] Synthesis, 1981, # 2, p. 155 - 156
[4] Advanced Synthesis and Catalysis, 2006, vol. 348, # 1-2, p. 243 - 248
[5] Journal of Molecular Catalysis A: Chemical, 2011, vol. 351, p. 41 - 45

N-BUTYL METHANESULPHONATE(1912-32-9)Related Product Information

• ISOPROPYL METHANESULFONATE
• P-TOLUENESULFONIC ACID N-BUTYL ESTER
• TATM
• Busulfan
• CYCLOHEXYL P-TOLUENESULFONATE
• (-)-1,4-DI-O-TOSYL-2,3-O-ISOPROPYLIDENETHREITOL
• Dodecyl 4-methylbenzenesulfonate
• 5'-Tosyladenosine
• Methyl 2,3-O-isopropylidene-5-O-(p-tolylsulfonyl)-beta-D-ribofuranoside
• 2'-TOSYLADENOSINE
• 2,2,3,3,4,4-HEXAFLUOROPENTANE-1,5-DIYL BIS(4-METHYLBENZENESULFONATE)
• METHYL 6-O-TOSYL-ALPHA-D-GLUCOPYRANOSIDE
• 1,6-ANHYDRO-3,4-O-ISOPROPYLIDENE-2-TOSYL-B-D-GALACTOPYRANOSE
• Butyl Benzenesulfonate
• P-TOLUENESULFONIC ACID (S)-2-METHYLBUTYL ESTER
• (S)-(+)-2-METHYLBUTYL METHANESULFONATE
• N-BUTYL METHANESULPHONATE
• 1,2-O-Isopropylidene-5-O-p-toluenesulfonyl-a-D-xylofuranose