3-Bromomethyl-3-oxetanemethanol Chemical Properties

Boiling point:

242℃

Density 

1.598

refractive index 

1.5130 to 1.5170

Flash point:

100°(212°F)

storage temp. 

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

form 

clear liquid

pka

14.58±0.10(Predicted)

color 

Colorless to Light yellow

CAS DataBase Reference

22633-44-9

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

23-26-37-60

RIDADR 

UN3265

TSCA 

No

HS Code 

2932209090

3-Bromomethyl-3-oxetanemethanol Usage And Synthesis

Synthesis

A. Synthesis of 3-bromomethyl-3-hydroxymethyl oxetane 2,2-Bis(bromomethyl)propane-1,3-diol (150 g, 0.573 mol) was dissolved in 650 mL of ethanol, followed by the slow addition of an ethanolic solution of sodium ethoxide (21%, 185.74 g, 0.573 mol) over 10 min. The reaction mixture was refluxed for 2 hours followed by stirring at room temperature for 16 hours. After completion of the reaction, the reaction mixture was filtered and the solvent was evaporated to give an oil containing solids. The crude product was dissolved in 200 mL of dichloromethane, filtered and the solvent was evaporated to give 98 g of crude 3-bromomethyl-3-hydroxymethoxetane. The crude product was purified by reduced pressure distillation (113°C, 3 mmHg) to give 52.95 g of pure product in 52% yield. NMR data: 1H NMR (δ, ppm): 3.75 (s, 2H), 3.88 (d, J = 4.9 Hz, 2H), 4.45 (s, 4H). 13C NMR (δ, ppm): 36.336 (t, J = 152.78 Hz), 45.0935 (s), 63.995 (t, J = 143.3 Hz), 77.216 (t, J = 152.78 Hz).

References

[1] Tetrahedron Letters, 2011, vol. 52, # 5, p. 565 - 567
[2] Patent: US5489700, 1996, A
[3] DRP/DRBP Org.Chem.,
[4] Journal of Organic Chemistry, 1956, vol. 21, p. 997
[5] Mededelingen van de Koninklijke Vlaamse Academie voor Wetenschappen, Letteren en Schone Kunsten van Belgie, Klasse der Wetenschappen, 1954, vol. 16, # 8, p. 3,10

3-Bromomethyl-3-oxetanemethanol(22633-44-9)Related Product Information

• 1-Bromo-2-methylpropane
• ISOBUTANE
• 3-Bromomethyl-3-oxetanemethanol
• 3-BROMOMETHYL-3-METHYLOXETANE
• 3-Methyl-3-oxetanemethanol