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262501

Sigma-Aldrich

5-Bromo-2-methyl-2-pentene

97%

Synonym(s):

1-Bromo-4-methyl-3-pentene, 2-Methyl-5-bromo-2-pentene, 4-Methyl-3-pentenyl bromide, 5-Bromo-2-methyl-2-pentene, 5-Bromo-2-methylpent-2-ene, Homoprenyl bromide, Prenylmethyl bromide

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About This Item

Linear Formula:
BrCH2CH2CH=C(CH3)2
CAS Number:
Molecular Weight:
163.06
Beilstein:
1735749
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

liquid

refractive index

n20/D 1.476 (lit.)

bp

152-154 °C (lit.)

density

1.217 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C\C(C)=C\CCBr

InChI

1S/C6H11Br/c1-6(2)4-3-5-7/h4H,3,5H2,1-2H3

InChI key

UNXURIHDFUQNOC-UHFFFAOYSA-N

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Application

5-Bromo-2-methyl-2-pentene has been used in the synthesis of:
  • geranlol-3-14C
  • penifulvin A, a sesquiterpenoid with a novel dioxa-fenestrane structure

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

71.6 °F - closed cup

Flash Point(C)

22 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tanja Gaich et al.
Journal of the American Chemical Society, 131(2), 452-453 (2009-01-15)
Herein we report the first total synthesis of Penifulvin A, a sesquiterpenoid with a novel dioxa-fenestrane structure. Penifulvin A is a potent insecticide against the fall armyworm Spodoptera frugiperda which causes enormous damage in the US by consuming foliage of
Biosynthesis of the vinca alkaloids. The incorporation of geraniol-3-14C into catharanthine and vindoline.
Leete E and Ueda S.
Tetrahedron Letters, 7(40), 4915-4918 (1966)

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