Geranyl bromide, 96%, Thermo Scientific Chemicals

Name: Geranyl bromide, 96%, Thermo Scientific Chemicals
SKU: ALFA14093.22

CAS: 6138-90-5 | C10H17Br | 217.15 g/mol

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100 g

5 g

Catalog number ALFA14093.22

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Chemical Identifiers

CAS617-86-7

IUPAC Nametriethylsilyl

Molecular FormulaC6H15Si

InChI KeyQXTIBZLKQPJVII-UHFFFAOYSA-N

SMILESCC[Si](CC)CC

Specifications

Specification Sheet

GC>=98.5 %

Refractive index1.4100 to 1.4120 (20°C, 589 nm)

Appearance (Color)Clear colorless

Appearance (Form)Liquid

Infrared spectrumConforms

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.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

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.

Solubility
Immiscible with water.

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

RUO – Research Use Only

General References:

Terpene building block.
The Horner reaction with Methyl diphenyl phosphine 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.