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Sigma-Aldrich

2-Bromo-3-methyl-2-butene

96%

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About This Item

Linear Formula:
(CH3)2C=C(Br)CH3
CAS Number:
3017-70-7
Molecular Weight:
149.03
MDL number:
MFCD00191852
UNSPSC Code:
12352100
PubChem Substance ID:
24863097
NACRES:
NA.22

Assay

96%

form

liquid

contains

copper pellets as stabilizer

refractive index

n20/D 1.474 (lit.)

bp

40 °C/75 mmHg (lit.)

density

1.284 g/mL at 25 °C (lit.)

SMILES string

C\C(C)=C(\C)Br

InChI

1S/C5H9Br/c1-4(2)5(3)6/h1-3H3

InChI key

DBELOSOZLGEZBM-UHFFFAOYSA-N

General description

2-Bromo-3-methyl-2-butene is a vinylic bromide compound. Palladium/di-1-adamantyl-n-butylphosphine-catalyzed reductive carbonylation of 2-bromo-3-methyl-2-butene has been reported. Cross-coupling reaction of 2-bromo-3-methyl-2-butene with potassium 6-(benzoyloxy)hexyltrifluoroborate and 3-(benzoyloxy)propyltrifluoroborate has been investigated.

Application

2-Bromo-3-methyl-2-butene may be used in the preparation of:
  • 2,3,4,5-tetramethyl-2,4-hexadiene
  • 2-iodo-3-methyl-2-butene
  • diastereomers of 2-amino-3-hydroxy-4,5-dimethylhexanoic acid
  • lithium reagent, 2-lithio-3-methylbut-2-ene
  • D-allo-(2R,3R,4R)-2-amino-3-hydroxy-4,5-dimethylhexanoic acid-containing peptide, pipecolidepsin A.

Pictograms

FlameSkull and crossbones
GHS02,GHS06

Signal Word

Danger

Hazard Statements

H226,H301

Hazard Classifications

Acute Tox. 3 Oral - Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

77.0 °F

Flash Point(C)

25 °C

Certificates of Analysis (COA)

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Synthesis of All the Diastereomers of 2-Amino-3-hydroxy-4, 5-dimethylhexanoic Acid.
Spengler J and Albericio F.
European Journal of Organic Chemistry, 1, 44-47 (2014)
Synthesis and Molecular Structure of 2, 3, 4, 5-Tetramethyl-2, 4-hexadiene.
Br M, et al.
Acta Chemica Scandinavica. Series B, 31, 387-390 (1977)
Marta Pelay-Gimeno et al.
Nature communications, 4, 2352-2352 (2013-08-31)
Pipecolidepsin A is a head-to-side-chain cyclodepsipeptide isolated from the marine sponge Homophymia lamellosa. This compound shows relevant cytotoxic activity in three human tumour cell lines and has unique structural features, with an abundance of non-proteinogenic residues, including several intriguing amino
Palladium/di-1-adamantyl-n-butylphosphine-catalyzed reductive carbonylation of aryl and vinyl halides.
Brennfuhrer A, et al.
Tetrahedron, 63(27), 6252-6258 (2007)
Artis Klapars et al.
Journal of the American Chemical Society, 124(50), 14844-14845 (2002-12-12)
A mild and general method for the conversion of aryl, heteroaryl, and vinyl bromides into the corresponding iodides was developed utilizing a catalyst system comprising 5 mol % of CuI and 10 mol % of a 1,2- or 1,3-diamine ligand.
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