1-Bromo-3-methyl-2-butene is considered as a source of 3,3-dimethylallyl group and used in the preparation of natural products. It is also employed in the synthesis of base-modified pyrimidine nucleosides. Further, it is used in the preparation of (±)-eldanolide, 1-(3,3-dimethylallyl)-L-tryptophan and (±)-fumagillin, an antibiotic isolated from Aspergillus fumigattus.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
1-Bromo-3-methyl-2-butene is considered as a source of 3,3-dimethylallyl group and used in the preparation of natural products. It is also employed in the synthesis of base-modified pyrimidine nucleosides. Further, it is used in the preparation of (±)-eldanolide, 1-(3,3-dimethylallyl)-L-tryptophan and (±)-fumagillin, an antibiotic isolated from Aspergillus fumigattus.
Solubility
Immiscible with water
Notes
Store in a cool place. Incompatible with strong oxidizing agents and strong bases
RUO – Research Use Only
General References:
- 3,3-Dimethylallyl (prenyl) building block group, useful in terpene synthesis. For use as an alkylating agent, see, e.g.: Org. Synth. Coll., 8, 381 (1993).
- In the presence of the hindered base lithium 2,2,6,6-tetramethylpiperidide (LTMP) forms a carbenoid species which reacts with alkenes to provide vinylcyclopropenes: Synlett, 647 (1991):
- Fujii, S.; Shimizu, A.; Takeda, N.; Oguchi, K.; Katsurai, T.; Shirakawa, H.; Komai, M.; Kagechika, H. Systematic synthesis and anti-inflammatory activity of μ-carboxylated menaquinone derivatives-Investigations on identified and putative vitamin K2 metabolites. Bioorg. Med. Chem. 2015, 23 (10), 2344-2352.
- Inagaki, R.; Ninomiya, M.; Tanaka, K.; Koketsu, M. Synthesis, Characterization, and Antileukemic Properties of Naphthoquinone Derivatives of Lawsone. ChemMedChem 2015, 10 (8), 1413-1423.