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Merck
CN

329118

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24859770
EC Number:
228-123-7
Beilstein/REAXYS Number:
1703631
MDL number:
MFCD00000243

Key Documents

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Product Name

Geranyl bromide, 95%

InChI key

JSCUZAYKVZXKQE-JXMROGBWSA-N

InChI

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

SMILES string

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

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.)

functional group

alkyl halide
bromo

storage temp.

2-8°C

Quality Level

100

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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.

General description

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

167.0 °F - closed cup

flash_point_c

75 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX8107
0000381088
0000381088
MKCT4208
MKCN0612

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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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