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A13388 1-Bromo-3-methyl-2-butene, 90+%, stab. with silver

CAS Number
870-63-3
Synonyms
3,3-Dimethylallyl bromide
Prenyl bromide

Stock No. Size Price ($) Quantity Availability
A13388-09 10g 34.80
A13388-18 50g 147.00
A13388-30 250g 714.00
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1-Bromo-3-methyl-2-butene, 90+%, stab. with silver

MDL
MFCD00000242
EINECS
212-799-5

Chemical Properties

Formula
C5H9Br
Formula Weight
149.03
Boiling Point
135°
Flash Point
32°(90°F)
Density
1.281
Refractive Index
1.4895
Storage & Sensitivity
Keep Cold. Light Sensitive.
Solubility
Immiscible with water

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.

Notes

Store in a cool place. Incompatible with strong oxidizing agents and strong bases

Literature 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.

GHS Hazard and Precautionary Statements

Hazard Statements: H226-H314-H335

Flammable liquid and vapour. Causes severe skin burns and eye damage. May cause respiratory irritation.

Precautionary Statements: P210-P233-P240-P243-P260-P264b-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P312-P363-P374-P380-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Ground/bond container and receiving equipment. Take precautionary measures against static discharge. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Call a POISON CENTER or doctor/physician if you feel unwell. Wash contaminated clothing before reuse. Fight fire with normal precautions from a reasonable distance. Evacuate area. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
1420778
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2903.39
TSCA
Yes

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