3-BROMOMETHYL-3-METHYLOXETANE Chemical Properties

Boiling point:

162℃

Density 

1.438

refractive index 

1.4800 to 1.4840

Flash point:

62℃

storage temp. 

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

form 

solid

color 

Colorless to Light yellow

InChI

InChI=1S/C5H9BrO/c1-5(2-6)3-7-4-5/h2-4H2,1H3

InChIKey

MGBZKWOJRYGRTO-UHFFFAOYSA-N

SMILES

O1CC(CBr)(C)C1

EPA Substance Registry System

Oxetane, 3-(bromomethyl)-3-methyl- (78385-26-9)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2932990090

3-BROMOMETHYL-3-METHYLOXETANE Usage And Synthesis

Uses

3-(Bromomethyl)-3-methyloxetane is a monomer for the synthesis of Poly 3-bromomethyl-3-Me oxetane (PolyBrMMO), an energetic thermoplastic elastomer for propellant formulations.

Synthesis

The general procedure for the synthesis of 3-bromomethyl-3-methyl-1-oxetane from 3-methyl-3-hydroxymethyl oxetane was as follows: 10 ml (0.1 mol) of 3-methyl-3-hydroxymethyl oxetane and 36.58 g (0.11 mol) of carbon tetrabromide were dissolved in 100 ml of dichloromethane. The reaction mixture was cooled to 0 °C under nitrogen protection and 31.56 g (0.12 mol) of triphenylphosphine was slowly added. Subsequently, the reaction mixture was warmed to room temperature and stirred continuously for 20 minutes. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. To the residue, 100 mL of ethyl acetate was added and filtered using diatomaceous earth to remove insoluble impurities. The filtrate was concentrated under reduced pressure and recrystallized by adding hexane. The mixture was again filtered using diatomaceous earth and the filtrate was concentrated under reduced pressure to give the crude product. Finally, 16 g of 3-bromomethyl-3-methyl-1-oxetane was obtained by fractional purification in 95% yield. The nuclear magnetic resonance hydrogen spectrum (1H NMR, CDCl3, 300 MHz) data of the product were as follows: δ 4.46-4.38 (double peak, 4H), 3.65 (single peak, 2H), 1.44 (single peak, 3H).

References

[1] Journal of Organic Chemistry, 1998, vol. 63, # 11, p. 3631 - 3646
[2] Patent: EP1927592, 2008, A1. Location in patent: Page/Page column 11
[3] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1981, p. 1406 - 1414
[4] Acta Chemica Scandinavica, 1991, vol. 45, # 1, p. 82 - 91
[5] Journal of Organic Chemistry, 1998, vol. 63, # 11, p. 3631 - 3646

3-BROMOMETHYL-3-METHYLOXETANE(78385-26-9)Related Product Information

• 3,3-BIS(BROMOMETHYL)OXETANE
• 3-BROMOMETHYL-3-METHYLOXETANE
• 3,3-DIMETHYLOXETANE
• 3-Bromomethyl-3-oxetanemethanol