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6138-90-5 - Geranyl bromide, 96% - 3,7-Dimethyl-2,6-octadienyl bromide - A14093 - Alfa Aesar

A14093 Geranyl bromide, 96%

CAS Number
6138-90-5
Synonyms
3,7-Dimethyl-2,6-octadienyl bromide

Size Price ($) Quantity Availability
5g 44.81
25g 143.17
100g 478.95
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Geranyl bromide, 96%

MDL
MFCD00000243
EINECS
228-123-7

Chemical Properties

Formula
C10H17Br
Formula Weight
217.16
Boiling Point
99-101°/10mm
Flash Point
95°(203°F)
Density
1.094
Refractive Index
1.5040
Sensitivity
Light Sensitive
Solubility
Immiscible with water.

Applications

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.

Notes

Store in a cool place. Incompatible with strong oxidizing agents.

Literature References

Terpene building block.

The Horner reaction with Methyl­diphenyl­phosphine oxide, A11484, provides a convenient access to the natural product (3Z,6E)-ɑ-farnesene, greatly superior to earlier multistep approaches: J. Org. Chem., 60, 6211 (1995):

Schmidt, J.; Adrian, J.; Stark, C. B. W. Short and highly efficient synthesis of lipid peroxidation inhibitor pyrrolostatin and some analogues thereof. Org. Biomol. Chem. 2015, 13 (30), 8173-8176.

Xu, L.; Liu, Z.; Dong, W.; Song, J.; Miao, M.; Xu, J.; Ren, H. Copper-free arylation of 3,3-disubstituted allylic halides with triazene-softened aryl Grignard reagents. Org. Biomol. Chem. 2015, 13 (22), 6333-6337.

GHS Hazard and Precautionary Statements

Hazard Statements: H318-H315-H335-H227

Causes serious eye damage. Causes skin irritation. May cause respiratory irritation. Combustible liquid.

Precautionary Statements: P210-P261-P280-P305+P351+P338-P304+P340-P310-P362-P312-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1422412
Harmonized Tariff Code
2903.39
TSCA
Yes

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