1-Bromo-3-methyl-2-butene, 90+%, stab. with silver, Thermo Scientific Chemicals
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1-Bromo-3-methyl-2-butene, 90+%, stab. with silver, Thermo Scientific Chemicals
Thermo Scientific Chemicals

1-Bromo-3-methyl-2-butene, 90+%, stab. with silver, Thermo Scientific Chemicals

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Catalog number A13388.09
also known as A13388-09
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Chemical Identifiers
CAS870-63-3
IUPAC Name1-bromo-3-methylbut-2-ene
Molecular FormulaC5H9Br
InChI KeyLOYZVRIHVZEDMW-UHFFFAOYSA-N
SMILESCC(C)=CCBr
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SpecificationsSpecification SheetSpecification Sheet
Assay (GC)> 90.0%
Appearance (Color)Colourless to yellow
Refractive Index1.4855-1.4935
Formliquid
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:

  1. 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).
  2. 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):
  3. 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.
  4. Inagaki, R.; Ninomiya, M.; Tanaka, K.; Koketsu, M. Synthesis, Characterization, and Antileukemic Properties of Naphthoquinone Derivatives of Lawsone. ChemMedChem 2015, 10 (8), 1413-1423.