Oxetan-3-yl Methanesulfonate

Oxetan-3-yl Methanesulfonate Property

Boiling point:

308.9±31.0 °C(Predicted)

Density 

1.38±0.1 g/cm3(Predicted)

storage temp. 

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

Appearance

White to off-white Solid

Safety

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HS Code 

29309090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

Oxetan-3-yl Methanesulfonate Chemical Properties,Usage,Production

Synthesis

To a solution of oxetan-3-ol (5 g, 67.5 mmol) and triethylamine (14.11 mL, 101 mmol) in dichloromethane (150 mL) was added methanesulfonyl chloride (6.79 mL, 88 mmol) dropwise at 0 °C. The reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, the solid was removed by filtration and the filtrate was washed sequentially with ice water and saturated saline. The organic phase was dried with anhydrous sodium sulfate and subsequently concentrated under reduced pressure to afford oxetan-3-yl methanesulfonate (11.7 g, 67.5 mmol, 100% yield) as an oil containing 12.2 wt% dichloromethane. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 3.06 (s, 3H), 4.79-4.82 (m, 2H), 4.86-4.90 (m, 2H), 5.52-5.49 (m, 1H).

References

[1] Patent: WO2013/55910, 2013, A1. Location in patent: Page/Page column 124; 125
[2] Patent: TW2017/8221, 2017, A. Location in patent: Page/Page column 98; 99
[3] Patent: WO2015/181186, 2015, A1. Location in patent: Page/Page column 169
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 23, p. 9769 - 9789
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 6, p. 2518 - 2532