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329118

Sigma-Aldrich

Geranyl bromide

95%

Synonym(s):

trans-1-Bromo-3,7-dimethyl-2,6-octadiene

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About This Item

Linear Formula:
(CH3)2C=CHCH2CH2C(CH3)=CHCH2Br
CAS Number:
6138-90-5
Molecular Weight:
217.15
Beilstein:
1703631
EC Number:
228-123-7
MDL number:
MFCD00000243
UNSPSC Code:
12352100
PubChem Substance ID:
24859770
NACRES:
NA.22

Assay

95%

form

liquid

refractive index

n20/D 1.504 (lit.)

bp

101-102 °C/12 mmHg (lit.)

density

1.094 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C\C(C)=C\CC\C(C)=C\CBr

InChI

1S/C10H17Br/c1-9(2)5-4-6-10(3)7-8-11/h5,7H,4,6,8H2,1-3H3/b10-7+

InChI key

JSCUZAYKVZXKQE-JXMROGBWSA-N

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General description

Geranyl bromide undergoes palladium catalyzed cross-coupling reaction with aryl and alkenylgold(I) phosphanes.

Application

Geranyl bromide was used in synthesis of baicalein and 3,7-dihydroxyflavone derivatives. It was also used in synthesis of potential flavonoidic modulators of P-glycoprotein activity.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

167.0 °F - closed cup

Flash Point(C)

75 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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M Maitrejean et al.
Bioorganic & medicinal chemistry letters, 10(2), 157-160 (2000-02-15)
A new series of potential flavonoidic modulators of P-glycoprotein activity has been prepared. The flavanolignan silybin was first oxidised to dehydrosilybin and then C-alkylated with either prenyl or geranyl bromide. The resulting isoprenoid dehydrosilybins were shown to display high in
Marta Perro Neves et al.
European journal of medicinal chemistry, 46(6), 2562-2574 (2011-04-19)
Fourteen baicalein and 3,7-dihydroxyflavone derivatives were synthesized and evaluated for their inhibitory activity against the in vitro growth of three human tumor cell lines. The synthetic approaches were based on the reaction with prenyl or geranyl bromide in alkaline medium
Miguel Peña-López et al.
Organic & biomolecular chemistry, 10(8), 1686-1694 (2012-01-24)
Aryl and alkenylgold(I) phosphanes react regioselectively with allylic electrophiles such as cinnamyl and geranyl halides (bromide, chloride and acetates) under palladium catalysis in THF at 80 °C to afford the α-substitution product with moderate to high yields. When the reaction

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