GERANYL BROMIDE

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CAS:6138-90-5
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CAS:6138-90-5
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  • CAS:6138-90-5
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GERANYL BROMIDE Basic information
Product Name:GERANYL BROMIDE
Synonyms:1-BROMO-3,7-DIMETHYL-2,6-OCTADIENE;GERANYL BROMIDE;TRANS-1-BROMO-3,7-DIMETHYL-2,6-OCTADIENE;(2E)-1-Bromo-3,7-dimethyl-2,6-octadiene;7-dimethyl-6-octadien(e)-1-bromo-3;(E)-1-bromo-3,7-dimethylocta-2,6-diene;Geranylbromide,97%;(2E)-1-Bromo-3,7-dimethyl-2,6-octadienine
CAS:6138-90-5
MF:C10H17Br
MW:217.15
EINECS:228-123-7
Product Categories:
Mol File:6138-90-5.mol
GERANYL BROMIDE Structure
GERANYL BROMIDE Chemical Properties
Boiling point 101-102 °C12 mm Hg(lit.)
density 1.094 g/mL at 25 °C(lit.)
refractive index n20/D 1.504(lit.)
Fp 203 °F
storage temp. 2-8°C
solubility soluble in Chloroform, Methanol
form Oil
color Clear Yellow to Pale Orange
Water Solubility Immiscible with water.
Sensitive Light Sensitive
BRN 1422412
InChI1S/C10H17Br/c1-9(2)5-4-6-10(3)7-8-11/h5,7H,4,6,8H2,1-3H3/b10-7+
InChIKeyJSCUZAYKVZXKQE-JXMROGBWSA-N
SMILESC\C(C)=C\CC\C(C)=C\CBr
CAS DataBase Reference6138-90-5(CAS DataBase Reference)
EPA Substance Registry System2,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)- (6138-90-5)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
RIDADR 2810
WGK Germany 3
8-10-19
TSCA TSCA listed
HazardClass 6.1(b)
PackingGroup III
Storage Class10 - Combustible liquids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
SigmaAldrich English
GERANYL BROMIDE Usage And Synthesis
UsesGeranyl bromide is used for the preparation of 3,7-dihydroxyflavone derivatives and baicalein. It is also involved in the synthesis of potential flavonoidic modulators of P-glycoprotein activity. Further, it reacts with benzenesulfinic acid to prepare geranyl phenyl sulfone. In addition to this, it takes part in the palladium catalyzed cross coupling with aryl and alkenylgold(I) phosphanes.
General DescriptionGeranyl bromide undergoes palladium catalyzed cross-coupling reaction with aryl and alkenylgold(I) phosphanes.
Synthesis
Geraniol

106-24-1

GERANYL BROMIDE

6138-90-5

General procedure for the synthesis of (E)-1-bromo-3,7-dimethylocta-2,6-diene from geraniol: Geraniol (10 g, 11.4 mL, 64.8 mmol, 1.0 eq.) was dissolved in dichloromethane (50 mL) under nitrogen protection. The solution was cooled to -20°C. A solution of phosphorus tribromide (3.0 mL, 32.4 mmol, 0.5 eq.) in dichloromethane (10 mL) was added slowly dropwise, keeping the reaction temperature below -16°C. The color of the solution changed to green/blue during the dropwise addition. The reaction mixture was stirred for 3 hours at about -20°C. Subsequently, water (50 mL) was carefully added at -40°C. The aqueous layer was extracted with ether (3 x 50 mL). The organic layers were combined and washed sequentially with saturated aqueous sodium bicarbonate (3 x 50 mL) and aqueous ammonium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a brown oily product (14.5 g, 66.6 mmol, quantitative yield).

References[1] Journal of the American Chemical Society, 1990, vol. 112, # 13, p. 5276 - 5290
[2] Synthesis, 1984, # 10, p. 876 - 881
[3] Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 5, p. 1456 - 1459
[4] Journal of the American Chemical Society, 2006, vol. 128, # 43, p. 14012 - 14013
[5] Advanced Synthesis and Catalysis, 2008, vol. 350, # 3, p. 365 - 369
Tag:GERANYL BROMIDE(6138-90-5) Related Product Information
Cupric bromide NICKEL(II) BROMIDE TRIHYDRATE Ethidium bromide Cuprous bromide Hydrogen bromide Copper(I) bromide-dimethyl sulfide INDIUM(III) BROMIDE Lithium bromide Potassium bromide Sodium bromide Zinc bromide Cyanogen bromide GERANYL BROMIDE TRANS,TRANS-FARNESYL BROMIDE GERANYL GERANYL BROMIDE 2,6-OCTADIENE ALL TRANS GERANYL GERANYL BROMIDE, [1-3H] TRANS, TRANS FARNESYL BROMIDE, [1-3H]

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