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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

302791-1G:
302791-VAR:
302791-5G:
302791-25G:
302791-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
0000381072
0000381072
0000191963
0000178530
MKBZ7469V

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A synthesis of moenocinol from isoprenoid precursors.
Bottger D and Welzel P.
Tetrahedron Letters, 24(47), 5201-5204 (1983)
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)
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
Minju Lee et al.
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