3,3-BIS(BROMOMETHYL)OXETANE Chemical Properties

Melting point:

25℃

Boiling point:

125℃ (23 Torr)

Density 

1.83 g/cm3(Temp: 25 °C)

storage temp. 

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

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Solid

color 

Colourless to Off-White

Stability:

Hygroscopic

InChI

InChI=1S/C5H8Br2O/c6-1-5(2-7)3-8-4-5/h1-4H2

InChIKey

QOPMHMFIIMJWET-UHFFFAOYSA-N

SMILES

O1CC(CBr)(CBr)C1

EPA Substance Registry System

Oxetane, 3,3-bis(bromomethyl)- (2402-83-7)

Safety Information

Hazard Codes 

Xn

Risk Statements 

34-22

Safety Statements 

26-36/37/39

RIDADR 

3265

WGK Germany 

3

HS Code 

2932990090

3,3-BIS(BROMOMETHYL)OXETANE Usage And Synthesis

Uses

3,3-Bis(bromomethyl)oxetane is a useful research chemical used in the preparation of tetrahydrofuran/thiolane derivatives.

Synthesis

2,2-Bis(bromomethyl)-3-bromo-1-propanol (200 g, 616 mmol) was used as raw material and dissolved in anhydrous ethanol (1 L). The freshly prepared sodium ethanol solution (253 mL, 677 mmol, 21% ethanol solution) was added slowly over 10 min at a temperature below 20 °C. The reaction mixture was heated to reflux temperature (76°C) during which a suspension was formed. After 3 hours of reaction, complete conversion of the feedstock was confirmed by GC analysis. Subsequently, the reaction mixture was cooled to room temperature and filtered to remove solid impurities. The filtrate was extracted by partitioning with methyl tert-butyl ether (MTBE, 400 mL) and water (550 mL). The aqueous phase was extracted once more with MTBE (250 mL). All organic phases were combined, washed sequentially with water (250 mL) and brine (150 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by a short-range distillation apparatus (56 °C/0.1 mbar) to give 3,3-bis(bromomethyl)oxetane 130 g (85% yield) as an almost colorless oil.1H NMR (CDCl3, 400 MHz) data: δ = 4.44 (s, 4H), 3.86 (s, 4H).

References

[1] Synthesis (Germany), 2017, vol. 49, # 11, p. 2394 - 2401
[2] Journal of Organometallic Chemistry, 2007, vol. 692, # 24, p. 5395 - 5402
[3] Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences, 1939, vol. 42, p. 778
[4] Chem. Zentralbl., 1940, vol. 111, # I, p. 2458
[5] Kogyo Kagaku Zasshi, 1958, vol. 61, p. 904,906

3,3-BIS(BROMOMETHYL)OXETANE(2402-83-7)Related Product Information

• Propionic anhydride
• Phthalic anhydride
• 3,3-BIS(BROMOMETHYL)OXETANE
• 1-BROMO-2-BROMOMETHYL-3-HYDROXY-PROPANE
• 3,3-DIMETHYLOXETANE
• 3-Bromo-2,2-dimethyl-1-propanol
• 3-BROMOMETHYL-3-METHYLOXETANE
• (R)-(-)-3-BROMO-2-METHYL-1-PROPANOL
• (S)-(+)-3-BROMO-2-METHYL-1-PROPANOL
• 1,3-DIBROMO-2,2-DIMETHYLPROPANE