1-BROMO-3,3-DIMETHYLBUTANE Chemical Properties

Melting point:

-44.22°C (estimate)

Boiling point:

147.26°C (estimate)

Density 

1.1497

refractive index 

1.4424

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

clear liquid

color 

Colorless to Almost colorless

InChI

InChI=1S/C6H13Br/c1-6(2,3)4-5-7/h4-5H2,1-3H3

InChIKey

ROKZAMCDHKVZIQ-UHFFFAOYSA-N

SMILES

C(Br)CC(C)(C)C

Safety Information

HS Code 

2903998090

1-BROMO-3,3-DIMETHYLBUTANE Usage And Synthesis

Uses

1-Bromo-3,3-dimethylbutane is a useful reagent for the preparation of macrocycles as modulators of CFTR in the treatment of cystic fibrosis.

Synthesis

General procedure for the synthesis of 3,3-dimethyl-1-butane from 3,3-dimethyl-1-butyrate: In a 1-liter round-bottomed flask fitted with a reflux condenser, the reaction mixture was cooled to 0°C in an ice bath, and 232 g of concentrated sulfuric acid and 283 g of hydrobromic acid (48% aqueous solution) were added sequentially. The mixture was refluxed for 6 h. After completion of the reaction, it was cooled to room temperature and the reaction was quenched by the addition of 400 g of ice. The aqueous phase was extracted with 400 ml of pentane and the combined organic layers were washed sequentially with methanol, aqueous NaOH and water. The organic layer was dried with anhydrous magnesium sulfate, filtered and the solvent was removed in vacuum. The product was purified by vacuum distillation to afford 88.1 g (55% yield) of 1-bromo-3,3-dimethylbutane as a colorless oily liquid. The structure of the product was confirmed by 1H-NMR (400 MHz, CDCl3): δ = 3.35 (m, 2H, CH2Br), 1.80 (m, 2H, CH2), 0.90 (s, 9H, t-Bu) ppm.

References

[1] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 3, p. 665 - 674
[2] Journal of the American Chemical Society, 1992, vol. 114, # 5, p. 1778 - 1784
[3] Patent: US8299287, 2012, B2. Location in patent: Page/Page column 53
[4] Patent: JP6196581, 2017, B2. Location in patent: Paragraph 0186
[5] Chemische Berichte, 1983, vol. 116, # 4, p. 1345 - 1363

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