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| | n-Butyl methanesulphonate Basic information |
| Product Name: | n-Butyl methanesulphonate | | Synonyms: | Imatinib Impurity Butyl Methane Sulfonate;Butylmethansulfonat;n-butylmethanesulfonate;BUTYL METHANE SULFONATE;BUTYLMESYLATE;n-Butyl mesylate~Methanesulphonic acid n-butyl ester;butyl methanesulphonate;n-Butylmesylate | | CAS: | 1912-32-9 | | MF: | C5H12O3S | | MW: | 152.21 | | EINECS: | 217-620-4 | | Product Categories: | | | Mol File: | 1912-32-9.mol |  |
| | 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 | | Major Application | pharmaceutical (small molecule) | | 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) |
| Hazard Codes | Xn | | Risk Statements | 22-36-43-36/37/38 | | Safety Statements | 26-36/37-37 | | WGK Germany | WGK 3 | | RTECS | PB1425000 | | HS Code | 29049090 | | Storage Class | 10 - Combustible liquids |
| | 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 Preparation Products And Raw materials |
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