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302791

Sigma-Aldrich

Geranyl chloride

95%

Synonym(s):

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

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About This Item

Linear Formula:
(CH3)2C=CHCH2CH2C(CH3)=CHCH2Cl
CAS Number:
5389-87-7
Molecular Weight:
172.69
MDL number:
MFCD00000983
UNSPSC Code:
12352100
PubChem Substance ID:
24858274
NACRES:
NA.22

Quality Level

100

Assay

95%

form

liquid

refractive index

n20/D 1.4808 (lit.)

bp

102-104 °C/12 mmHg (lit.)

density

0.931 g/mL at 25 °C (lit.)

functional group

alkyl halide
chloro

SMILES string

C\C(C)=C\CC\C(C)=C\CCl

InChI

1S/C10H17Cl/c1-9(2)5-4-6-10(3)7-8-11/h5,7H,4,6,8H2,1-3H3/b10-7+

InChI key

WLAUCMCTKPXDIY-JXMROGBWSA-N

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General description

Geranyl chloride undergoes palladium-catalyzed cross-coupling reaction with aryl and alkenylgold(I) phosphanes to afford the α-substitution product.

Application

Geranyl chloride was used as starting reagent in the synthesis of:
  • C25 compound moenocinol
  • 2-methyl-6-geranylphenol
  • manoalide and seco-manoalide analogs

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)

194.0 °F - closed cup

Flash Point(C)

90 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBZ7469V
MKBN3062V
MKBK9294V
14307BD
11209BI

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Preparation and oxidative polymerization of 2-methyl-6-geranylphenol.
Hyun SH, et al.
Polymer Bull., 18(4), 283-286 (1987)
Toward elucidation of the inhibition mechanism of phospholipase A< sub> 2</sub> by manoalide: selectively modified amino acid residues by manoalide analogues.
Katsumura S, et al.
Bioorganic & Medicinal Chemistry Letters, 2(10), 1267-1268 (1992)
A synthesis of moenocinol from isoprenoid precursors.
Bottger D and Welzel P.
Tetrahedron Letters, 24(47), 5201-5204 (1983)
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
Lisa Becks et al.
BMC cancer, 10, 540-540 (2010-10-12)
Activation of nuclear factor erythroid 2-related factor (Nrf2), which belongs to the basic leucine zipper transcription factor family, is a strategy for cancer chemopreventive phytochemicals. It is an important regulator of genes induced by oxidative stress, such as glutathione S-transferases
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