| Identification | Back Directory | [Name]
4-BroMo-2-Methylbutan-2-ol | [CAS]
35979-69-2 | [Synonyms]
4-BroMo-2-Methylbutan-2-ol
4-BroMo-2-Methyl-2-butanol
2-Butanol, 4-broMo-2-Methyl-
4-BroMo-2-hydroxy-2-Methylbutane
4-BroMo-2-Methylbutan-2-ol ISO 9001：2015 REACH | [Molecular Formula]
C5H11BrO | [MDL Number]
MFCD20483824 | [MOL File]
35979-69-2.mol | [Molecular Weight]
167.04 |
| Chemical Properties | Back Directory | [Boiling point ]
189.7±23.0 °C(Predicted) | [density ]
1.371±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Chloroform, Ethyl Acetate | [form ]
Oil | [pka]
14.79±0.29(Predicted) | [color ]
Brown | [InChI]
InChI=1S/C5H11BrO/c1-5(2,7)3-4-6/h7H,3-4H2,1-2H3 | [InChIKey]
RBFVGQWGOARJRU-UHFFFAOYSA-N | [SMILES]
CC(C)(O)CCBr |
| Hazard Information | Back Directory | [Chemical Properties]
4-BroMo-2-Methylbutan-2-ol is Brown Oil
| [Uses]
4-Bromo-2-methyl-2-butanol is a brominated tertiary alcohol used as a reagent in the preparation of vitamin D3 analogues. | [Synthesis]
General procedure for the synthesis of 4-bromo-2-methyl-2-butanol from ethyl 3-bromopropionate and methylmagnesium bromide: To a solution of ethyl 3-bromopropionate (0.2 g, 1.2 mmol) in tetrahydrofuran (THF, 5 mL) was slowly added methylmagnesium bromide (2.4 mL, 2.4 mmol) at 0°C. The reaction mixture was stirred continuously until a thin layer chromatography (TLC) analysis showed complete consumption of the raw material. The reaction mixture was stirred continuously at 0°C until thin layer chromatography (TLC) analysis showed complete consumption of the raw material [Unfolding agent: petroleum ether/ethyl acetate (3:1), Rf value of the product was 0.3]. Upon completion of the reaction, the reaction was quenched with aqueous ammonium chloride (2 mL) at 0°C. The reaction mixture was extracted with ethyl acetate and water by partitioning. The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated to give the crude product. The crude product was purified by column chromatography using petroleum ether/ethyl acetate (3:1) as eluent to give 4-bromo-2-methyl-2-butanol (0.15 g, 75.1% yield) as a yellow oil. | [References]
[1] Patent: WO2014/143799, 2014, A2. Location in patent: Page/Page column 403
[2] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 2, p. 525 - 535
[3] Journal of Organometallic Chemistry, 1973, vol. 47, p. 337 - 350
[4] Tetrahedron Letters, 1992, vol. 33, # 1, p. 105 - 108
[5] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 10, p. 828 - 833 |
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