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.)

Flash point:

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

InChIKey

JSCUZAYKVZXKQE-JXMROGBWSA-N

CAS DataBase Reference

6138-90-5(CAS DataBase Reference)

EPA Substance Registry System

2,6-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

F 

8-10-19

TSCA 

Yes

HazardClass 

6.1(b)

PackingGroup 

III

MSDS

• Language:English Provider:SigmaAldrich

GERANYL BROMIDE Usage And Synthesis

Uses

Geranyl 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 Description

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

Synthesis

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

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]